Title: Book The Best Hotels in Southold, NY for 2025 from CA $128 - Compare prices by date | 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=2025-10-22&d1=2025-10-22&endDate=2025-10-24&d2=2025-10-24&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=2025-10-22&d1=2025-10-22&endDate=2025-10-24&d2=2025-10-24&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=2025-10-22&d1=2025-10-22&endDate=2025-10-24&d2=2025-10-24&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=2025-10-22&d1=2025-10-22&endDate=2025-10-24&d2=2025-10-24&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=2025-10-22&d1=2025-10-22&endDate=2025-10-24&d2=2025-10-24&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=2025-10-22&d1=2025-10-22&endDate=2025-10-24&d2=2025-10-24&lodging=COTTAGE)

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=2025-10-22&d1=2025-10-22&endDate=2025-10-24&d2=2025-10-24&lodging=APARTMENT)

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=2025-10-22&d1=2025-10-22&endDate=2025-10-24&d2=2025-10-24&travelerType=family_friendly)

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=2025-10-22&d1=2025-10-22&endDate=2025-10-24&d2=2025-10-24&amenities=WATER_PARK)

## Check prices for these dates

Tonight

[Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-08&endDate=2025-10-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 9 - Oct 10](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-09&endDate=2025-10-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Compare 4,313 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)

![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)

![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/81035eb2.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)

### The Shoals Suites and Slips

Southold

9.6/10

Exceptional

(211)

"Great quick stay"

CA $307

CA $386 total

includes taxes & fees

Oct 15 - Oct 16

[](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)

![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)

![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)

### Hampton Bays Hotel on Main

Hampton Bays

7.0/10

Good

(63)

"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!"

CA $169

CA $193 total

includes taxes & fees

Nov 2 - Nov 3

[](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)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/f7da52a9.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)

### Saybrook Point Resort & Marina

Old Saybrook Center

9.4/10

Exceptional

(1007)

"Great place!! "

CA $363

CA $452 total

includes taxes & fees

Nov 5 - Nov 6

[](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)

![Exterior](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/55438f97.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)

![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)

### The Atlantic Hotel

Southampton

7.2/10

Good

(948)

"Very nice staff and great location "

[](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)

![Desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a48f4b96.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

(1005)

"Very friendly and helpful staff."

CA $112

CA $128 total

includes taxes & fees

Oct 27 - Oct 28

[](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)

![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)

![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/9f1bca91.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

(667)

"Love this place "

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

![Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/98ce732d.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)

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

### Ocean Vista Resort

Amagansett

9.0/10

Wonderful

(196)

"Lovely short stay! Right on the beautiful beach. Staff were so welcoming and even quickly sent me something I accidentally left behind in the room. Absolutely plan to be back!"

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

![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)

![Villa, Multiple Beds, Ground Floor (by the Sea) | Beach/ocean view](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/25adc215.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)

### Water's Edge Resort & Spa

Westbrook Center

8.8/10

Excellent

(1004)

"clean and quiet property, great views, amazing staff"

CA $306

CA $375 total

includes taxes & fees

Oct 19 - Oct 20

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

(275)

"Clean and quiet right on a main street with plenty of shopping and dining. Very close to the vineyards. Great stay."

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

![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/2000000/1380000/1374000/1373980/8aa4b577.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

(744)

"Clean and comfortable "

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

![Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/64ea9871.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)

![Harbor View Balcony Junior Suite | Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/e407cc6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Harbor Front Inn

Greenport

8.8/10

Excellent

(521)

"Great location ,beautiful hotel,nice staff"

CA $230

CA $332 total

includes taxes & fees

Nov 2 - Nov 3

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

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/511d84f6.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)

### Quality Inn Old Saybrook - Westbrook

Old Saybrook

7.6/10

Good

(1006)

"We have stayed there before so have been pleased with it."

CA $130

CA $150 total

includes taxes & fees

Nov 2 - Nov 3

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

![Junior Suite, 1 King Bed](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/cd124626.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)

![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

(364)

"Great room, very spacious "

CA $316

CA $361 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Riverhead-Hotels-The-Preston-House-Hotel.h21825843.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/a37c2d73.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/11000000/10220000/10211600/10211593/6142ad8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton's Vacation Inn

Hampton Bays

9.0/10

Wonderful

(317)

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

CA $176

CA $201 total

includes taxes & fees

Oct 9 - Oct 10

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

![Property grounds](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/a7102e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/e78d099b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/c7d19019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Greenporter Hotel

Greenport

9.2/10

Wonderful

(262)

"Staff was amazing and this hotel is in the perfect location "

CA $207

CA $237 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.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/2000000/1210000/1209400/1209378/1ef9d54f.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)

![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

(321)

"the staff was exceptional and our dinner was very good"

CA $414

CA $477 total

includes taxes & fees

Nov 3 - Nov 4

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

![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)

![Seasonal outdoor pool, open 8:00 AM to 7:30 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/3fa39065.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

(1002)

"Excellent facility and staff. Room was spacious and extremely clean. Look forward to staying here every trip to Long Island!"

CA $205

CA $235 total

includes taxes & fees

Oct 27 - Oct 28

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

![Seasonal outdoor pool, open 9:00 AM to 8:00 PM, free cabanas](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/5ed206f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fishing](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/eb1df3cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic Penthouse, 2 Queen Beds, Bay View | Living area](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/cd50a48f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sundeck](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/5785cca7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bayview Resort

Hampton Bays

8.8/10

Excellent

(447)

"Staff was fantastic, room was always clean and the area was perfect! "

CA $228

CA $260 total

includes taxes & fees

Oct 9 - Oct 10

[](https://www.expedia.ca/Hampton-Bays-Hotels-Bayview-Resort.h10453825.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)

![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)

![Lobby](https://images.trvl-media.com/lodging/2000000/1970000/1962600/1962521/w3837h2557x3y3-564a2b5d.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)

### Hilton Garden Inn Riverhead

Riverhead

8.6/10

Excellent

(1001)

"Very nice hotel and convenient to vineyards "

CA $216

CA $247 total

includes taxes & fees

Oct 27 - Oct 28

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

![Building design](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/1c345cd0.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)

### Sag Harbor Inn

Sag Harbor

9.4/10

Exceptional

(557)

"Great place to stay!"

CA $262

CA $300 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.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=2025-10-22&endDate=2025-10-23&regionId=183719&adults=2&sort=RECOMMENDED&openPlayBack=true)

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

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## Learn more about Southold

Come to Southold and enjoy its wineries, island views, and beaches.

[See all hotels in Southold](https://www.expedia.ca/Hotel-Search?startDate=2025-10-22&endDate=2025-10-23&adults=2&regionId=183719)

![](https://mediaim.expedia.com/destination/1/2af9844708ff5148df98a90729e7edaf.jpg?impolicy=fcrop&w=900&h=600&p=1&q=high)

### 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

![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

[Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F10%2F2025&endDate=23%2F10%2F2025&selected=447803&PinnedHotelID=447803&HadPinnedHotel=true&regionId=183719)

7/10 Good! (948 reviews)

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

![Greenview Inn Riverhead](https://images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/12e5dcab_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Greenview Inn Riverhead

1433 W Main St, Riverhead, NY

[Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F10%2F2025&endDate=23%2F10%2F2025&selected=1373980&PinnedHotelID=1373980&HadPinnedHotel=true&regionId=183719)

7.2/10 Good! (743 reviews)

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

![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 27 - Oct 28

includes taxes & fees

7.8/10 Good! (1,005 reviews)

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

![Greenporter Hotel](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Greenporter Hotel

326 Front St, Greenport, NY

CA $207

CA $237 total

Oct 13 - Oct 14

includes taxes & fees

9.2/10 Wonderful! (260 reviews)

[](https://expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.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 $223

CA $255 total

Nov 2 - Nov 3

includes taxes & fees

9.4/10 Exceptional! (348 reviews)

[](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.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 2 - Nov 3

includes taxes & fees

7.6/10 Good! (1,003 reviews)

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

54 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

242 properties

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

![2 Star Hotels](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_w.jpg)

2 Star Hotels

214 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.*

### 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

"Great place, beautiful views! I’ll be back."

A verified traveller stayed at The Shoals Suites and Slips

Posted 2 days ago

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

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

### Greenview Inn Riverhead

5/5 Excellent

"I was really impressed with the modern, clean room. I loved the sliding barn door..clean, white bedding & refillable soap & shampoo & conditioner. No more little plastic bottles that never hold enough to even wash one person’s hair. I also lined the separate reading lights. The gentleman checking us in was pleasant and it took a very short time. I would definitely consider another visit next time I am visiting the North Fork of Long Island."

A verified traveller stayed at Greenview Inn Riverhead

Posted 2 days ago

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

"Clean room!!"

A verified traveller from Tampa stayed at The Bentley Hotel Southampton

Posted 3 days ago

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

![Saybrook Point Resort & Marina](//images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg)

### Saybrook Point Resort & Marina

5/5 Excellent

"Relaxing wonderful staff!"

A verified traveller stayed at Saybrook Point Resort & Marina

Posted 3 days ago

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

![Hotel Indigo East End by IHG](//images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/75016698_y.jpg)

### Hotel Indigo East End by IHG

5/5 Excellent

"Great experience, loved the bartender and happy hour. Very friendly staff ."

A verified traveller stayed at Hotel Indigo East End by IHG

Posted 4 days ago

[](https://expedia.ca/Riverhead-Hotels-Hotel-Indigo-East-End.h3475618.Hotel-Information)

![Greenporter Hotel](//images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f_y.jpg)

### Greenporter Hotel

5/5 Excellent

"Great stay! Lovely people! Great area!"

A verified traveller stayed at Greenporter Hotel

Posted 4 days ago

[](https://expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information)

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

### Sound View Greenport

5/5 Excellent

"Nice views on sunset"

A verified traveller stayed at Sound View Greenport

Posted 5 days ago

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

![Water's Edge Resort & Spa](//images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg)

### Water's Edge Resort & Spa

5/5 Excellent

"Beautiful grounds, well maintained property. Our room was clean and comfortable. Definitely want to come back and extend our stay with family and friends. It’s a beautiful escape on the East Coast "

A verified traveller stayed at Water's Edge Resort & Spa

Posted 5 days ago

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

"We were there 1 night, so i didnt notice shops. But there was a good restaurant across the road."

A verified traveller from STATEN ISLAND stayed at Quality Inn Old Saybrook - Westbrook

Posted 6 days ago

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

## Frequently asked questions

### What are the best hotels in Southold that travellers recommend?

> [The Shoals Suites and Slips](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) is a highly praised destination in Southold, boasting an impressive traveller review score of 9.4. This charming hotel is great for couples seeking a romantic getaway, offering premium bedding, luxurious bathrobes, and attentive champagne service that sets the mood for an intimate experience. Guests love the opportunity to explore nearby vineyards with private tours and tastings, making it a delightful choice for wine enthusiasts looking to unwind in a serene setting.
> 
>   
> 
> For families, [Vine & Sand](https://www.expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information) stands out with a great review score of 10.0. This hotel promises comfort and convenience, featuring premium bedding and designer toiletries that ensure a restful stay. Families will appreciate the spacious rooms and the opportunity to enjoy the beautiful vineyard views right from their doorstep. With rainfall showerheads and a friendly setting, it's an inviting spot for relaxation after a day of exploring local attractions.

### What are the best family hotels in Southold?

> [The Shoals Suites and Slips](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) in Southold stands out as an exceptional family-friendly hotel, boasting a stellar review score of 9.4 from guests who appreciate its attentive service and comfortable accommodations. This charming property offers a range of amenities designed to cater to families, including complimentary cribs and a daily housekeeping service, ensuring that parents can enjoy a stress-free stay while their little ones are well taken care of. Find more [child-friendly accommodations in Southold](https://www.expedia.ca/Southold-Hotels-Family-Hotel.0-0-d183719-tFamilyHotel.Travel-Guide-Filter-Hotels).

### What hotels in Southold offer free breakfast?

> [Vine & Sand](https://www.expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information) in Southold is an exceptional choice for travellers seeking a serene retreat complemented by attentive service. With a superb customer review rating of 10.0, this hotel stands out not only for its picturesque vineyard views but also for its delightful amenities. Find more [hotels with free breakfast in Southold](https://www.expedia.ca/Southold-Hotels-Hotels-With-Free-Breakfast.0-0-d183719-tHotelsWithFreeBreakfast.Travel-Guide-Filter-Hotels).

### What are the top pet-friendly hotels in Southold?

> [The Shoals Suites and Slips](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) in Southold, NY, is a charming pet-friendly hotel that welcomes furry companions while offering an exceptional stay for their owners. This beautifully situated property boasts a stunning white sand beach, great for morning strolls with your pet. Guests rave about the attentive service and thoughtful amenities, including premium bedding, air conditioning, and a kitchenette, ensuring a comfortable and convenient experience. See more [pet-friendly hotels in Southold](https://www.expedia.ca/Southold-Hotels-Pet-Friendly-Hotel.0-0-d183719-tPetFriendlyHotel.Travel-Guide-Filter-Hotels).

### What are the best budget hotels in Southold?

> For travellers seeking charming accommodations in Southold, [Vine & Sand](https://www.expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information) is an exceptional option, boasting a great review score of 10.0. This hotel offers a delightful array of amenities, including free Wi-Fi and complimentary breakfast on weekends, ensuring a comfortable stay without breaking the bank. Guests can enjoy the seasonal outdoor pool, relax on the terrace, or take in the beautiful vineyard views. The nearby private beach with sun loungers and umbrellas provides an ideal spot for families to unwind.
> 
>   
> 
> Another top property is [The Shoals Suites and Slips](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information), which has received high praise with a traveller review score of 9.4. This hotel features a kitchenette in each suite, great for families who prefer the convenience of preparing their own meals. The property also offers access to a stunning white sand beach and organizes public tours and tastings at their on-site winery, making it a fantastic choice for couples looking for a romantic getaway while still appealing to families. View all [budget hotels in Southold](https://www.expedia.ca/Southold-Hotels-Cheap-Hotels.0-0-d183719-tCheapHotels.Travel-Guide-Filter-Hotels).

### What are the most romantic hotels in Southold for couples?

> For couples seeking a romantic escape, [The Shoals Suites and Slips](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) in Southold is an exceptional choice, boasting an impressive customer review rating of 9.4. This hotel features an array of amenities designed to enhance your romantic getaway, including couples dining options that set the stage for intimate meals together. See all [romantic hotels in Southold](https://www.expedia.ca/Southold-Hotels-Romantic-Hotel.0-0-d183719-tRomanticHotel.Travel-Guide-Filter-Hotels).

### When is the best time to go to Southold?

> The most popular time to visit Southold is during the summer months, particularly July, when the weather is warm and inviting. With average temperatures ranging from 22 to 27°C, this is the superb season for enjoying the beautiful beaches, exploring local wineries, and taking part in outdoor activities.
> 
>   
> 
> During the peak season, which runs from June to August, Southold comes alive with vibrant tourist activity. Visitors flock to the area for its stunning coastal views and charming small-town atmosphere. This time of year is especially enjoyable for those who appreciate leisurely days spent cycling through scenic vineyards or indulging in fresh seafood at waterfront restaurants, where you can savour the local cuisine while soaking in the sun.
> 
>   
> 
> For families and couples alike, July offers numerous festivals and events that showcase the best of Southold's culture and community spirit. Whether it's a local art fair or a concert in the park, there's always something happening to enhance your visit. The long days and pleasant evenings provide ample time to explore and relax.
> 
>   
> 
> If you're looking for a slightly quieter experience, consider planning your trip in September. The weather remains pleasant, with temperatures still hovering around 20 to 24°C, and you'll find that prices for accommodations and activities often drop as the summer crowds disperse. This is a wonderful opportunity to enjoy the area's natural beauty without the hustle and bustle of peak season.

### Can I cancel my 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. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Southold hotel for you.

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

> With Expedia, you'll unlock our lowest prices by becoming a 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 Southold hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings.

### How much is the nightly rate at a Southold hotel?

> Prices for hotels in Southold often vary, but you can find a great deal from CA $128 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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-   [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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