Title: Book The Best Hotels in Southold, NY for 2025 from CA $128 - Competitive Prices - Expedia.ca

  

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![Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod. ](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Benny Goh

# Find hotels in Southold, NY from CA $128

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## Go beyond your typical stay in Southold

Spa

[](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2025-11-12&d1=2025-11-12&endDate=2025-11-14&d2=2025-11-14&amenities=SPA_ON_SITE)

Ocean view

[](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2025-11-12&d1=2025-11-12&endDate=2025-11-14&d2=2025-11-14&amenities=OCEAN_VIEW)

Pet friendly

[](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2025-11-12&d1=2025-11-12&endDate=2025-11-14&d2=2025-11-14&amenities=PETS)

Hot tub

[](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2025-11-12&d1=2025-11-12&endDate=2025-11-14&d2=2025-11-14&amenities=HOT_TUB)

Pool

[](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2025-11-12&d1=2025-11-12&endDate=2025-11-14&d2=2025-11-14&amenities=POOL)

Cottage

[](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2025-11-12&d1=2025-11-12&endDate=2025-11-14&d2=2025-11-14&lodging=COTTAGE)

Family friendly

[](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2025-11-12&d1=2025-11-12&endDate=2025-11-14&d2=2025-11-14&travelerType=family_friendly)

Apart­ment

[](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2025-11-12&d1=2025-11-12&endDate=2025-11-14&d2=2025-11-14&lodging=APARTMENT)

Waterpark

[](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2025-11-12&d1=2025-11-12&endDate=2025-11-14&d2=2025-11-14&amenities=WATER_PARK)

## Check prices for these dates

Tonight

[Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-29&endDate=2025-10-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Compare 4,308 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

![Garden Suite King](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace King](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/efe41897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/81035eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/22f2b7c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Shoals Suites and Slips

Southold

9.6/10

Exceptional

(218)

"Great quick stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jasmine T

CA $243

CA $313 total

includes taxes & fees

Nov 29 - Nov 30

[](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information)

![Deluxe Double Room, 1 King Bed, City View](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/e3ee1fa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/a206dde5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Double Room | Private kitchenette](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/b36c7eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/ff8b5175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Bays Hotel on Main

Hampton Bays

7.0/10

Good

(65)

"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Olivia

CA $164

CA $188 total

includes taxes & fees

Nov 1 - Nov 2

[](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Bays-Hotel-On-Main.h106830297.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, 2 outdoor pools, open 5:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/8957afe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/65651fbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/770255ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Saybrook Point Resort & Marina

Old Saybrook Center

9.4/10

Exceptional

(1005)

"Beautiful property, we loved our room, friendly staff. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Natalie

CA $331

CA $416 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Honeymoon Room, Jetted Tub](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/5fc9f561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/806c49e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/55438f97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Atlantic Hotel

Southampton

7.2/10

Good

(961)

"Very nice staff and great location "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Granger

CA $144

CA $199 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/72f65e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/31bd2f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/afdef753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

8.0/10

Very good

(1001)

"Always a great stay at Pier Blue. Comfy bed and plenty of room."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Patricia

CA $112

CA $128 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/e820e996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/34576327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/74fca349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/e70cf1f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Hampton Maid

Hampton Bays

9.0/10

Wonderful

(676)

"Was so lovely would definitely come back again, very cute clean and safe "

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Maria

CA $262

CA $300 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Maid-Motel.h19715959.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/ccd49f89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/5c6281d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Couples treatment rooms, sauna, hot tub, steam room, body treatments](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/533d1f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Water's Edge Resort & Spa

Westbrook Center

8.8/10

Excellent

(1011)

"We love the stay everything was perfect"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

angelica

CA $305

CA $375 total

includes taxes & fees

Oct 31 - Nov 1

[](https://www.expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information)

![Indoor pool, open 9:00 AM to 9:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/0b15e4f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/8ffa2c0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/9aa57818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Old Saybrook - Westbrook

Old Saybrook

7.8/10

Good

(1010)

"Everything was good, had a quiet happy stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Aishwariya

CA $130

CA $150 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden Suite, Wheelchair Accessible, Ground Floor, 2 Queen Beds, Non-Smoking](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/20957ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/942c49f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/bfb5cc4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Zey Hotel

Greenport

9.2/10

Wonderful

(282)

"Such a cute little hotel. Stayed one night bc we had a wedding in the area. Everything was great - the staff was exceptional."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Phyllis

CA $367

CA $419 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information)

![One Bedroom Harbor View Terrace Suite | View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/a8d80546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/4e8534b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/64ea9871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Harbor Front Inn

Greenport

8.8/10

Excellent

(526)

"Beautiful view and room. Staff friendly and accommodating. Excellent location. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

John

CA $244

CA $347 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)

![Deluxe Double Room](https://images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/d1b868c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Single Room](https://images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/1802c026.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Studio Suite](https://images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/58338103.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Studio Suite](https://images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/73ba7bc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Greenview Inn Riverhead

Riverhead

7.4/10

Good

(760)

"Nicely refurbished rooms. Very clean"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Karen

CA $150

CA $172 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Riverhead-Hotels-Greenview-Inn-Riverhead.h1373980.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/a4958436.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/1ef9d54f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/625fce42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Madison Beach Hotel

Madison Center

9.4/10

Exceptional

(327)

"Beautiful hotel ! Great waterviews, staff and restaurant food !"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kim

CA $342

CA $393 total

includes taxes & fees

Nov 13 - Nov 14

[](https://www.expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/ae918eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/fc8f49f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/7454864c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sport court](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/20fb5209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ocean Vista Resort

Amagansett

9.0/10

Wonderful

(198)

"Such a beautiful place to stay. Pam at the front was so nice and welcoming. The room was clean it was quiet and everyone was friendly. Love that it has a private beach! Would 10/10 recommend it and deff will be going back."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

kayla c

[](https://www.expedia.ca/Amagansett-Hotels-Ocean-Vista-Resort.h9388116.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/1f765cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/e64d0e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/6a60f683.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/783d70b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Preston House & Hotel

Riverhead

9.8/10

Exceptional

(366)

"Staff was amazing, include the restaurants’ staff! 2nd time staying there, will be back for many more!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nakia

CA $247

CA $283 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Riverhead-Hotels-The-Preston-House-Hotel.h21825843.Hotel-Information)

![Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/15a14a38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/04aa4e82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/d096a355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/e77eab74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hamlet Inn

Southampton

8.6/10

Excellent

(433)

"A solid inexpensive stay in the Hamptons. Staff are very accommodating, they helped guide us when there was an upcoming storm. Room was comfortable and clean. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michelle

CA $143

CA $185 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information)

![Apartment, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/4e100a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/6142ad8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's activities](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/949a0d23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/a37c2d73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton's Vacation Inn

Hampton Bays

9.0/10

Wonderful

(323)

"A great Hampton location that's less than a thirty minutes drive from Coopers Beach and South Hampton main street."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Maggie

CA $188

CA $215 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Hampton-Bays-Hotels-Bowens-By-The-Bays.h10211593.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/6b467104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/5f09bd5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Down comforters, pillowtop beds, desk, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/5d4f757e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/5a99aefa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Hotel & Suites Long Island-East End by IHG

Riverhead

8.6/10

Excellent

(1001)

"Very friendly and clean "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Carrie

CA $206

CA $236 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Riverhead-Hotels-Holiday-Inn-Express-Hotel-Suites-Long-Island-East-End.h1376205.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/14a9b9bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/d11f2952.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/f95ca887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/db237a24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sag Harbor Inn

Sag Harbor

9.4/10

Exceptional

(561)

"We had lovely stay, the staff was knowledgeable, efficient, and friendly. Will visit again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lori

CA $262

CA $300 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1970000/1962600/1962521/82ff92d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Snack bar](https://images.trvl-media.com/lodging/2000000/1970000/1962600/1962521/98baffa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1970000/1962600/1962521/w3837h2557x3y3-b7e16408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, outdoor pool, open 8:00 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1970000/1962600/1962521/be16e1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Riverhead

Riverhead

8.6/10

Excellent

(1000)

"Convenient location "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Corin

CA $191

CA $218 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Riverhead-Hotels-Hilton-Garden-Inn-Riverhead.h1962521.Hotel-Information)

![Property amenity](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/b5361d70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Banquet hall](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/53fa5839.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Banquet hall](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/ff7ccdb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/2ffae8cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence Inn by Marriott New York Long Island East End

Riverhead

9.2/10

Wonderful

(999)

"Great staff, very clean and modern facility, nicely appointed rooms, and a lot of things nearby to do."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mary J

CA $212

CA $242 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Riverhead-Hotels-Residence-Inn-By-Marriott-New-York-Long-Island-East-End.h18516036.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-12&endDate=2025-11-13&regionId=183719&adults=2&sort=RECOMMENDED&openPlayBack=true)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSouthold-Hotels.d183719.Travel-Guide-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthold-Hotels.d183719.Travel-Guide-Hotels)

## Learn more about Southold

Vineyards and farm stands dot the landscape of this North Fork gem, inviting visitors to sample local wines and fresh produce. Stroll along the pebble beaches, explore historic lighthouses, or take a ferry to nearby Shelter Island for a day trip.

[See all hotels in Southold](https://www.expedia.ca/Hotel-Search?startDate=2025-11-12&endDate=2025-11-13&adults=2&regionId=183719)

![Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod. ](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=899&h=600&p=1&q=high)

Photo by Benny Goh

### Stay near popular Southold attractions

[](https://expedia.ca/Sparkling-Pointe-Hotels.0-l6327589-0.Travel-Guide-Filter-Hotels)

![Sparkling Pointe](https://mediaim.expedia.com/destination/2/3f9e84132c7cf86c180b2490717bed52.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Sparkling Pointe

You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6327589)

[](https://expedia.ca/Sanninos-Bella-Vita-Vineyard-Hotels.0-l6327435-0.Travel-Guide-Filter-Hotels)

#### Sannino's Bella Vita Vineyard

You can enjoy a tasting or tour at Sannino's Bella Vita Vineyard during your travels to Southold. Wander the beaches or discover the sunsets in this family-friendly area.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6327435)

[](https://expedia.ca/Croteaux-Vineyards-Hotels.0-l6326852-0.Travel-Guide-Filter-Hotels)

#### Croteaux Vineyards

You can enjoy a tasting or tour at Croteaux Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6326852)

[](https://expedia.ca/Ospreys-Dominion-Hotels.0-l6326243-0.Travel-Guide-Filter-Hotels)

#### Osprey's Dominion

You can enjoy a tasting or tour at Osprey's Dominion during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6326243)

[](https://expedia.ca/Corey-Creek-Winery-Hotels.0-l6326844-0.Travel-Guide-Filter-Hotels)

#### Corey Creek Winery

You can enjoy a tasting or tour at Corey Creek Winery during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6326844)

[](https://expedia.ca/Horton-Point-Park-Hotels.0-l6064489-0.Travel-Guide-Filter-Hotels)

#### Horton Point Park

Explore the great outdoors at Horton Point Park, a lovely green space in Southold. Wander the beaches or discover the sunsets in this family-friendly area.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6064489)

## More cheap stays in Southold

![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd, Old Saybrook, CT

CA $112

CA $128 total

Oct 30 - Oct 31

includes taxes & fees

7.8/10 Good! (1,011 reviews)

[](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information)

![Quality Inn Old Saybrook - Westbrook](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Quality Inn Old Saybrook - Westbrook

100 Essex Rd, Old Saybrook, CT

CA $130

CA $150 total

Nov 9 - Nov 10

includes taxes & fees

7.6/10 Good! (1,008 reviews)

[](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information)

![The Atlantic Hotel](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Atlantic Hotel

1655 County Road 39, Southampton, NY

CA $144

CA $199 total

Oct 30 - Oct 31

includes taxes & fees

7/10 Good! (961 reviews)

[](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information)

![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Bentley Hotel Southampton

161 Hills Station Rd, Southampton, NY

CA $208

CA $237 total

Nov 4 - Nov 5

includes taxes & fees

9.4/10 Exceptional! (364 reviews)

[](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information)

![Spark by Hilton Guilford](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Spark by Hilton Guilford

300 Boston Post Rd, Guilford, CT

CA $122

CA $141 total

Nov 29 - Nov 30

includes taxes & fees

8.6/10 Excellent! (48 reviews)

[](https://expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information)

![Budget Host East End Hotel in Riverhead](https://images.trvl-media.com/lodging/2000000/1140000/1130500/1130479/ad0c5cd3_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Budget Host East End Hotel in Riverhead

30 Lake Avenue, Riverhead, NY

CA $144

CA $165 total

Oct 30 - Oct 31

includes taxes & fees

6.6/10 (757 reviews)

[](https://expedia.ca/Riverhead-Hotels-Budget-Host-East-End-Hotel-In-Riverhead.h1130479.Hotel-Information)

## Hotels in Southold with star-rating

![5 Star Hotels](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/e0e0def6_w.jpg)

5 Star Hotels

2 properties

[](https://expedia.ca/5Star-Southold-Hotels.s50-0-d183719.Travel-Guide-Filter-Hotels)

![4 Star Hotels](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_w.jpg)

4 Star Hotels

55 properties

[](https://expedia.ca/4Star-Southold-Hotels.s40-0-d183719.Travel-Guide-Filter-Hotels)

![3 Star Hotels](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_w.jpg)

3 Star Hotels

237 properties

[](https://expedia.ca/3Star-Southold-Hotels.s30-0-d183719.Travel-Guide-Filter-Hotels)

![2 Star Hotels](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_w.jpg)

2 Star Hotels

235 properties

[](https://expedia.ca/2Star-Southold-Hotels.s20-0-d183719.Travel-Guide-Filter-Hotels)

## Find out more about Southold

### Top reasons to visit Southold

-   **Picturesque Beaches:** Southold features stunning sandy shores, perfect for relaxing or enjoying a family day by the water.
-   **Outdoor Adventures:** Engage in various activities like paddleboarding in the summer or skiing in the winter.
-   **Local Culture:** Explore charming spots like the Southold Fish Market for a taste of local flavours.
-   **Scenic Picnic Areas:** Enjoy beautiful picnic spots amidst Southold's natural beauty.
-   **Diverse Accommodations:** Choose from a range of lodging options, including family-friendly and pet-friendly stays.

### Find great hotels near Southold

Southold, New York, offers a diverse array of accommodations to cater to every traveller's needs, from family-friendly stays to pet-friendly options. Notably, the Southold Beach Motel stands out for its charming atmosphere and proximity to the stunning shoreline. Whether you're seeking adventure or a relaxing getaway, you'll find the perfect lodging to enhance your experience in this picturesque coastal town.

-   **[Sound View Greenport:](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)** Nestled along the picturesque shoreline, Sound View Greenport offers a delightful blend of beachside relaxation and family-friendly amenities. This 3.5-star hotel is perfect for those looking to unwind by the water while enjoying a range of activities suitable for all ages. With direct beach access, you can soak up the sun or partake in water sports. Business travellers will appreciate the well-equipped meeting rooms and conference space, while families can take advantage of amenities designed for children, including free cribs and window guards for added safety.
-   **[Sag Harbor Inn:](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information)** Located a short drive from Southold, Sag Harbor Inn is an excellent choice for business travellers seeking a tranquil environment. This 3.5-star hotel is designed with professionalism in mind, offering essential business amenities including a meeting room that caters to corporate needs. The hotel's serene surroundings provide a peaceful atmosphere, allowing you to focus on your work while enjoying the charm of Sag Harbor. Guests have noted the attentive service and comfortable accommodations that make this inn a reliable option for business trips.
-   **[The Harbor Front Inn:](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)** The Harbor Front Inn stands out as a pet-friendly haven for travellers wanting to bring their furry companions along. This 3.5-star hotel, conveniently located near Southold, combines business amenities with a welcoming atmosphere for pets. With policies that allow dogs and service animals, you won't have to leave your pet behind. Business travellers can benefit from a range of facilities designed to cater to their needs, while enjoying the unique experience of a waterfront stay. Guests have praised the incredible location and accommodating staff, ensuring a comfortable visit for both you and your pet.

### Where to stay near Southold

Southold, New York, offers an idyllic vacation experience perfect for outdoor enthusiasts and couples alike. With its stunning beaches and beachfront locations, it's an ideal beach getaway for families and those seeking relaxation. Nearby attractions provide a blend of scenic beauty, historical charm, and luxury excursions. Whether you're enjoying sunny weather or planning a weekend escape, Southold promises a delightful atmosphere for every traveller.

-   **[Hamptons:](https://www.expedia.ca/Hamptons-Hotels.d6056452.Travel-Guide-Hotels)** Located a mere 16.1km from Southold, the Hamptons are a quintessential summer destination known for their beautiful beaches and upscale charm. This area sees a peak in visitors from June to August, attracting those seeking a beach , outdoor , and romantic experience. With golf courses, music concerts, and luxurious resorts, there’s no shortage of activities to indulge in. Additionally, the picturesque local landmarks, including family-friendly beaches and serene lakes, make the Hamptons a perfect getaway for relaxation and recreation.
-   **[Greenport:](https://www.expedia.ca/Greenport-Hotels.d110728.Travel-Guide-Hotels)** Just 6.4km away from Southold, Greenport is a charming city that offers a delightful mix of outdoor activities and romantic vibes. Like the Hamptons, Greenport experiences peak travel from June to August, drawing visitors who enjoy beaches and local events. Golf courses and music concerts abound, providing ample entertainment options. The proximity to beautiful beaches and event conference venues adds to Greenport’s appeal, making it a must-visit for those looking to experience the coastal lifestyle.
-   **[Sag Harbor:](https://www.expedia.ca/Sag-Harbor-Hotels.d154327.Travel-Guide-Hotels)** Located 12.9km from Southold, Sag Harbor is a picturesque city that perfectly encapsulates a coastal retreat. The area enjoys a moderate influx of visitors, especially from June to August, who come for its outdoor , beach , and romantic experiences. From golf courses to ski fields, the range of activities is impressive. Sag Harbor is also home to beautiful beaches, family parks, and scenic spots, making it an ideal location for both adventure and relaxation.

### Things to do near Southold

Southold, New York, is perfect for a romantic and outdoor getaway, offering a variety of activities. Enjoy relaxing beach days on the sandy shores, have a picnic in scenic areas, or soak up the sun on the terrace. For the adventurous, paddleboard rentals are available, and there are opportunities for winter sports like skiing. Additionally, music concerts provide entertainment options, making Southold an ideal vacation destination.

**Shopping**

In Southold, visit the [Greenport Farmers' Market](https://www.expedia.ca/Greenport-Farmers-Market-Hotels.0-l553248621532665744-0.Travel-Guide-Filter-Hotels), only 6.4km away, for fresh produce and local crafts. [The Style Bar](https://www.expedia.ca/The-Style-Bar-Hotels.0-l553248621532665737-0.Travel-Guide-Filter-Hotels) and [BookHampton](https://www.expedia.ca/BookHampton-Hotels.0-l553248621532665731-0.Travel-Guide-Filter-Hotels), both 12.9km away, offer unique fashion and books. If you're up for a drive, check out larger malls in nearby towns for more extensive shopping options.

**Recreation**

[Goldsmith's Inlet Park](https://www.expedia.ca/Goldsmiths-Inlet-Park-Hotels.0-l6326890-0.Travel-Guide-Filter-Hotels) offers a tranquil escape with its calming natural surroundings, perfect for relaxation and rejuvenation. For those seeking sport and outdoor fun, [Noyac Golf Club](https://www.expedia.ca/Noyac-Golf-Club-Hotels.0-l6064499-0.Travel-Guide-Filter-Hotels) provides a beautiful golf experience, while [Shelter Island Whale's Tail](https://www.expedia.ca/Shelter-Island-Whales-Tail-Hotels.0-l553248621554204762-0.Travel-Guide-Filter-Hotels) mini-golf promises family-friendly adventure in a delightful setting.

**Adventure**

Experience thrilling water rides at [Splish Splash Water Park](https://www.expedia.ca/Splish-Splash-Water-Park-Hotels.0-l6173416-0.Travel-Guide-Filter-Hotels), located 30.6km from Southold, perfect for family fun. For adrenaline junkies, [Riverhead Raceway](https://www.expedia.ca/Riverhead-Raceway-Hotels.0-l6173429-0.Travel-Guide-Filter-Hotels) offers exciting motor racing action, situated 29.0km away. Don't miss the scenic [Walking Dunes Trailhead](https://www.expedia.ca/Walking-Dunes-Trailhead-Hotels.0-l553248633992587102-0.Travel-Guide-Filter-Hotels), 33.8km from Southold, for a picturesque hiking adventure.

**Nightlife**

Experience the charm of the [Greenport Carousel](https://www.expedia.ca/Greenport-Carousel-Hotels.0-l553248635961252285-0.Travel-Guide-Filter-Hotels), just 6.4km away, offering a whimsical outdoor vibe. For a touch of culture and romance, head to [Bay Street Theatre](https://www.expedia.ca/Bay-Street-Theatre-Hotels.0-l6326787-0.Travel-Guide-Filter-Hotels), 12.9km from Southold, or [Guild Hall](https://www.expedia.ca/Guild-Hall-Hotels.0-l6323757-0.Travel-Guide-Filter-Hotels), 16.4km away, both perfect for family entertainment.

*\*Distances are measured in a straight line; actual driving distances may vary depending on the route.*

### Booking tips and Expedia advantages for Southold

To save money on your trip to Southold, consider visiting between January and March when accommodation prices drop. Tuesdays tend to be the least expensive days to stay, while Saturdays are pricier. Use Expedia's search tool to find budget-friendly hotels by sorting prices from lowest to highest and filtering for eco-friendly options. Additionally, you can save by booking a package that combines your hotel, flights, and activities. Exploring the area on foot is a great way to enjoy free activities while keeping transport costs down.

-   **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Southold are January to March, where the prices are slightly lower. This is in comparison to June to August, where prices are slightly higher.
-   **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Southold is Tuesday. The most expensive day to stay in Southold is Saturday.
-   **Find cheap hotels on Expedia:** Expedia’s search tool enables you to specify your budget, preferred destination, and additional criteria. You can arrange your search results to display prices from lowest to highest, making it easy to find the most affordable hotels first. Furthermore, you have the option to narrow down your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly accommodations that you can book.
-   **Consider bundling your trip:** You can potentially save some money by combining your Southold hotel reservation with your flights and activities through an Expedia package.

### Find the best attractions near Southold

Southold, New York, is perfect for outdoor enthusiasts and romantic getaways, offering a blend of beach experiences, cultural attractions, and history. Visitors can enjoy the scenic Southold Town Beach and explore local gems like the Southold Fish Market. The area caters to those seeking relaxation by the shore, engaging outdoor activities, and a taste of local culture, making it an ideal destination for a memorable vacation.

-   **[67 Steps Beach:](https://www.expedia.ca/67-Steps-Beach-Hotels.0-l553248626388140598-0.Travel-Guide-Filter-Hotels)** Located 8.0km from Southold, 67 Steps Beach offers a delightful seaside experience with its picturesque views and relaxing beach vibes. It's perfect for sunbathing, swimming, and enjoying the tranquil sounds of the waves.
-   **[Railroad Museum of Long Island:](https://www.expedia.ca/Railroad-Museum-Of-Long-Island-Hotels.0-l6327144-0.Travel-Guide-Filter-Hotels)** Just 6.4km away, this cultural gem showcases the rich history of Long Island's railroads. Explore fascinating exhibits and learn about the region's transportation heritage in a family-friendly environment.
-   **[Sag Harbor Marine Park:](https://www.expedia.ca/Sag-Harbor-Marine-Park-Hotels.0-l6327316-0.Travel-Guide-Filter-Hotels)** Situated 12.9km from Southold, this marina is ideal for outdoor enthusiasts. Enjoy various water activities, unwind on the beach, and take in the scenic beauty of the surrounding area for a perfect adventure.

### Best time to go to Southold

The best time to visit Southold is dependant on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately low and weather is mostly sunny with light rain.

| **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** |
| --- | --- | --- | --- | --- | --- |
| January | 35.6°F (2.0°C) | Light Rain | Mostly Sunny | Moderately Low | Slightly Low |
| February | 35.8°F (2.1°C) | Light Rain | Mostly Cloudy | Average | Slightly Low |
| March | 39.7°F (4.3°C) | Light Rain | Mostly Sunny | Average | Slightly Low |
| April | 47.5°F (8.6°C) | Light Rain | Mostly Sunny | Average | Average |
| May | 55.8°F (13.2°C) | Light Rain | Mostly Sunny | Average | Average |
| June | 64.9°F (18.3°C) | Light Rain | Mostly Sunny | Moderately High | Slightly High |
| July | 73.0°F (22.8°C) | Light Rain | Mostly Sunny | Moderately High | Slightly High |
| August | 73.4°F (23.0°C) | Light Rain | Mostly Sunny | Moderately High | Slightly High |
| September | 68.2°F (20.1°C) | Light Rain | Mostly Sunny | Average | Average |
| October | 59.7°F (15.4°C) | Light Rain | Mostly Sunny | Average | Average |
| November | 49.6°F (9.8°C) | Light Rain | Mostly Sunny | Moderately Low | Average |
| December | 42.1°F (5.6°C) | Light Rain | Mostly Cloudy | Moderately Low | Average |

### The nearest major airports for your trip to Southold

For your visit to Southold, New York, you have several airport options. Islip, NY ([ISP](https://www.expedia.ca/MacArthur-Airport-Hotels.0-aISP-0.Travel-Guide-Filter-Hotels)\-MacArthur) is located 64.4km away, with nearby hotels such as the 3.5-star [Hyatt Regency Long Island](https://www.expedia.ca/Hauppauge-Hotels-Hyatt-Regency-Long-Island.h3668.Hotel-Information), Jake's 58 Casino Hotel, and Radisson Hotel Hauppauge, each offering convenient access to the airport. New Haven, CT ([HVN](https://www.expedia.ca/Tweed-New-Haven-Regional-Airport-Hotels.0-aHVN-0.Travel-Guide-Filter-Hotels)\-Tweed - New Haven Regional) is 45.1km distant, featuring 4-star accommodations like [The Blake Hotel](https://www.expedia.ca/New-Haven-Hotels-The-Blake-Hotel.h32129620.Hotel-Information) and [Graduate by Hilton New Haven](https://www.expedia.ca/New-Haven-Hotels-Graduate-New-Haven.h37200005.Hotel-Information). East Hampton, NY ([HTO](https://www.expedia.ca/East-Hampton-Airport-Hotels.0-aHTO-0.Travel-Guide-Filter-Hotels)) is the closest at 19.3km, with luxurious options such as the 5-star [Mill House Inn](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information) and the 4.5-star [Topping Rose House](https://www.expedia.ca/Bridgehampton-Hotels-Topping-Rose-House.h5581380.Hotel-Information), ensuring a comfortable stay while being near the airport.

## Recent reviews of Southold hotels

![The Shoals Suites and Slips](//images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8_y.jpg)

### The Shoals Suites and Slips

5/5 Excellent

"Everything was Amazing! "

A verified traveller stayed at The Shoals Suites and Slips

Posted 1 day ago

[](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information)

![The Bentley Hotel Southampton](//images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg)

### The Bentley Hotel Southampton

5/5 Excellent

"The staff was beyond helpful and nice, the rooms are huge and clean. Would definitely recommend "

A verified traveller stayed at The Bentley Hotel Southampton

Posted 1 day ago

[](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information)

![Spark by Hilton Guilford](//images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2_y.jpg)

### Spark by Hilton Guilford

5/5 Excellent

"I need an overnight stay with decent accomodations - this fit well inside my price range and comfort."

A verified traveller stayed at Spark by Hilton Guilford

Posted 1 day ago

[](https://expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information)

![The Atlantic Hotel](//images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg)

### The Atlantic Hotel

5/5 Excellent

"Perfect "

A verified traveller stayed at The Atlantic Hotel

Posted 1 day ago

[](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information)

![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg)

### Sound View Greenport

5/5 Excellent

"Beautiful Long Island Sound and sunset views."

A verified traveller stayed at Sound View Greenport

Posted 1 day ago

[](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)

![Greenview Inn Riverhead](//images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/d1b868c8_y.jpg)

### Greenview Inn Riverhead

5/5 Excellent

"The place is a little bit outdated nature a little bit of uplift but other than that it's still the best deal on Long Island and especially around Riverhead. Well worth the $97 that they are charging, but every other place is $200 and not worth it."

A verified traveller stayed at Greenview Inn Riverhead

Posted 2 days ago

[](https://expedia.ca/Riverhead-Hotels-Greenview-Inn-Riverhead.h1373980.Hotel-Information)

![The Harbor Front Inn](//images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg)

### The Harbor Front Inn

5/5 Excellent

"Beautiful view and room. Staff friendly and accommodating. Excellent location. "

A verified traveller stayed at The Harbor Front Inn

Posted 2 days ago

[](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)

![Quality Inn Old Saybrook - Westbrook](//images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg)

### Quality Inn Old Saybrook - Westbrook

5/5 Excellent

"Everything was good, had a quiet happy stay."

A verified traveller stayed at Quality Inn Old Saybrook - Westbrook

Posted 2 days ago

[](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information)

![Zey Hotel](//images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978_y.jpg)

### Zey Hotel

5/5 Excellent

"Such a cute little hotel. Stayed one night bc we had a wedding in the area. Everything was great - the staff was exceptional."

A verified traveller stayed at Zey Hotel

Posted 2 days ago

[](https://expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information)

## Frequently asked questions

### What are the best hotels in Southold with outdoor pools?

> [Vine & Sand](https://www.expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information) is a charming 3-star hotel in Southold that offers a delightful outdoor pool, great for families looking to relax after a day of adventure. Guests rave about the lovely rooms, making it a comfortable choice for travellers of all kinds.
> 
>   
> 
> In addition to its inviting pool, Vine & Sand provides a range of amenities that enhance the stay for families. Enjoy complimentary breakfast on weekends, and take advantage of free WiFi to stay connected or plan your excursions. The hotel also offers self-parking at no extra cost, making it convenient for those driving to the area. With bicycles available for guests, exploring the beautiful surroundings becomes an enjoyable family activity.

### How much does a hotel with outdoor pool in Southold cost?

> Enjoy staying in a hotel in Southold with an outdoor pool. You can find a great deal from CA $128 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.

### Are there hotels in Southold with outdoor pool cabanas or loungers?

> [Vine & Sand](https://www.expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information) is a charming 3-star hotel in Southold that offers a delightful outdoor pool area, superb for families looking to relax in the sun. Guests have praised the lovely rooms, making it a cozy retreat after a day of adventure.
> 
>   
> 
> The outdoor pool features beach sun loungers, allowing you to soak up the sun comfortably while enjoying the serene surroundings. Additionally, the hotel provides convenient amenities like free WiFi and complimentary breakfast on weekends, enhancing your stay with quality and value.

### Is it cheaper to book flights and a hotel in Southold as a package?

> Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package.

### How can I save on a hotel in Southold with Expedia?

> Before booking your Southold hotel, remember to join Expedia's free travel rewards program—[One Key™](https://www.expedia.ca/welcome-one-key). Just sign up and sign in to access our lowest Member Prices as well as members-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.

### Can I cancel my hotel reservation on Expedia?

> Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel with an outdoor pool in Southold for you.

### Is Southold a family-friendly destination?

> Yes, Southold is a wonderfully family-friendly destination, offering a relaxed coastal atmosphere with plenty of activities and amenities great for families.
> 
>   
> 
> Southold boasts beautiful, calm beaches along the Peconic Bay, ideal for children to paddle in the shallow waters and build sandcastles. Many of these beaches also have playgrounds nearby, providing extra entertainment. The area is dotted with open green spaces and local parks, great for a picnic or a game of frisbee.
> 
>   
> 
> Getting around Southold is quite pleasant; many areas are walkable, especially the charming village centre with its local shops and eateries. For longer distances, cycling is a popular option, with several flat paths suitable for families.
> 
>   
> 
> You'll find a good selection of casual, family-friendly restaurants offering delicious local fare, often with outdoor seating.

### What family-friendly activities should we do in Southold?

> Some of the best family-friendly activities to do in Southold include exploring the beaches, visiting local farms for berry picking, and enjoying the many parks and green spaces.
> 
>   
> 
> Southold boasts beautiful, calm beaches like Southold Town Beach and Kenney's Beach, which are great for children to play in the sand and splash in the gentle waters. These spots often have picnic areas and open spaces for families to relax and enjoy the coastal atmosphere together.
> 
>   
> 
> Visiting a local farm for berry picking, such as those found along the North Fork, offers a delightful hands-on experience for the whole family. Many farms also have farm stands where you can pick up fresh produce and local treats, making for a lovely outing.
> 
>   
> 
> For outdoor play, Southold offers several parks and recreational areas. These green spaces often feature playgrounds, open fields for games, and walking paths ideal for a leisurely family stroll.

### How can I save on a family-friendly hotel in Southold with Expedia?

> With Expedia, you'll unlock our lowest prices by becoming a [One Key™](https://www.expedia.ca/welcome-one-key) member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on family-friendly Southold hotels. Typically, booking in advance will help you save on your hotel stay. If you're feeling spontaneous, be sure to check for last-minute deals.

### Can I cancel my family hotel reservation on Expedia?

> Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right family-friendly hotel in Southold for you.

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-   [Adults Only Resorts & in Silver Beach](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels-Adults-Only-Resorts.0-n553248635976481903-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
-   [Silver Beach Hotels](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels.0-n553248635976481903-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Sunset Beach](https://www.expedia.ca/Sunset-Beach-Hotels.0-l553248626388141313-0.Travel-Guide-Filter-Hotels)
-   [The Heights Hotels](https://www.expedia.ca/The-Heights-Shelter-Island-Heights-Hotels.0-n553248635976473534-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Wades Beach](https://www.expedia.ca/Wades-Beach-Hotels.0-l553248621554204759-0.Travel-Guide-Filter-Hotels)

-   [Flights to Greenport](https://www.expedia.ca/Cheap-Flights-To-Greenport.d110728.Travel-Guide-Flights)
-   [Flights to Shelter Island](https://www.expedia.ca/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)
-   [Flights from Shelter Island](https://www.expedia.ca/lp/flights/157359/flights-from-shelter-island)
-   [Flights from Toronto (YYZ) to New York (NYC)](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york)

-   [Bedell Cellars](https://www.expedia.ca/Bedell-Cellars-Cutchogue.d553248621532665643.Vacation-Attraction)
-   [Visit Pipes Cove](https://www.expedia.ca/Greenport-Pipes-Cove.dx553248635976473295)
-   [Kontokosta Winery](https://www.expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction)
-   [Pindar Vineyards](https://www.expedia.ca/Pindar-Vineyards-Peconic.d6326965.Vacation-Attraction)
-   [Shelter Island Heights Vacations](https://www.expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides)
-   [Visit Shelter Island](https://www.expedia.ca/Shelter-Island.dx157359)

-   [Car rental Greenport](https://www.expedia.ca/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide)
-   [Car rental Shelter Island](https://www.expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)

-   [Cutchogue Vacation Rentals](https://www.expedia.ca/Cutchogue-Vacation-Rentals.d183659.Travel-Guide-VacationRentals)
-   [Shelter Island Vacation Rentals](https://www.expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)

-   [Things to do in Greenport](https://www.expedia.ca/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities)
-   [Things to do in Shelter Island Heights](https://www.expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities)
-   [Things to do in Shelter Island](https://www.expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)

-   [Book Hotels in Southold on Expedia.com](https://www.expedia.com/Southold-Hotels.d183719.Travel-Guide-Hotels)

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