Title: Southold Chalets from CA $116 | Expedia.ca

 

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# Search Chalets in Southold from CA $116

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## Check prices for these dates

Next weekend

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Southold Chalets

We don't have any properties that match your exact search

[See all properties in Southold](https://expedia.ca/Hotel-Search?startDate=2025-11-19&endDate=2025-11-20&regionId=183719&adults=2)

## Recommended hotels in Southold

![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)

![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)

![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

(219)

"Great quick stay"

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

Jasmine T

CA $248

CA $284 total

includes taxes & fees

Dec 6 - Dec 7

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

![Exterior](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/5d25c168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/a9ca389a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/59bbc572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/63390424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vine & Sand

Southold

9.6/10

Exceptional

(13)

"My husband and I escaped to Long Island for a beautiful fall weekend and thoroughly enjoyed our stay at Vine + Sand. The hosts were very friendly and helpful with restaurant reservations and offered great tips for local activities. The accommodations were eco-friendly, modern and super comfortable and the breakfast in the morning offered delicious pastries and other homemade foods from local bakeries and markets which were a great touch. The location was private yet close enough to get to town...

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

Heather

[](https://www.expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/1be24cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/5f36ce70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/52e5aba4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, printers](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/30fcbecb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautifully farmhouse

Southold

10/10

Exceptional

(3)

"good experience"

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

Anonymous traveller

CA $843

CA $1,651 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Southold-Hotels-Magic-Place.h113098265.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/735ceae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Combined shower/tub, hair dryer, towels, soap](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/afd83ae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/dc9b088b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/bc78fd2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spark by Hilton Guilford

Guilford

8.6/10

Excellent

(49)

"Good clean property with great staff "

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

David

CA $149

CA $171 total

includes taxes & fees

Nov 16 - Nov 17

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

![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)

![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 $197

CA $293 total

includes taxes & fees

Nov 20 - Nov 21

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

![Free self parking](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/7836a152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/f2520f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free self parking](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/5e85d188.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/7bb1af0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Clinton Motel

Clinton

8.6/10

Excellent

(289)

"Clean and neat place "

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

john

CA $110

CA $126 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/724b2312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage, 2 Bedrooms, Patio](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/9f6ba503.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage, 1 Bedroom, Patio](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/e582d722.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/876a0e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### North Fork Cottages & RV Resort

Greenport

10/10

Exceptional

(1)

"Great stay! Very clean and new. Comfy beds, great location "

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

Lisa

CA $275

CA $314 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/9371eb14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, coffee/tea maker, cookware/dishes/utensils, spices](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/b6de66d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/691fdd98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/5b4c06e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Stern at Soundview · Beach+Ocean+Sunrise

Old Lyme

10/10

Exceptional

(3)

"Perfect for a weekend beach getaway. Very small but accurately portrayed in the pictures. It was clean and the host was very helpful and responsive. "

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

Olivia C.

CA $107

CA $273 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/334e85c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/1bfd9996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/ec2d268d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/4bbf34cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Bentley Hotel Southampton

Southampton

9.6/10

Exceptional

(367)

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

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

Ingrid

CA $164

CA $188 total

includes taxes & fees

Nov 16 - Nov 17

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

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/8d844436.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![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)

### Quality Inn Old Saybrook - Westbrook

Old Saybrook

7.8/10

Good

(1011)

"It was a nice clean hotel. "

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

Rhona

CA $125

CA $144 total

includes taxes & fees

Dec 1 - Dec 2

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/11d8806e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![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)

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

### Hamlet Inn

Southampton

8.6/10

Excellent

(434)

"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 $144

CA $186 total

includes taxes & fees

Nov 6 - Nov 7

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

![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/7564e116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/509e7634.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/ee8b7737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/f90ba663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Shorewood Inn

Riverhead

8.6/10

Excellent

(703)

"Bed was very comfortable.. staff was very friendly.. loud traffic in AM.. good water pressure.. would stay here again. "

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

Shelly

[](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information)

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

![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f.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)

![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)

### Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

8.0/10

Very good

(1002)

"Great place to stay!"

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

Nancy

CA $113

CA $129 total

includes taxes & fees

Nov 11 - Nov 12

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

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

![Exterior](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978.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)

![Lobby](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/dc9e5678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Zey Hotel

Greenport

9.2/10

Wonderful

(283)

"Funky decor, nice seating areas, great location"

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

Nicholas G

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

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/5a24caee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/f1ad96fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/3da43463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/a79f88d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New and Modern Bridgehampton Accommodations

Bridgehampton

9.6/10

Exceptional

(15)

"Had a great stay here with a small group. Host was very accommodating and responsive. "

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

Alyssa M.

CA $247

CA $609 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Bridgehampton-Hotels-New-And-Modern-Bridgehampton-Accommodations.h105953388.Hotel-Information)

![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/55b708b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/4c9856c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 2 Queen Beds](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/f76cf168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sound View Greenport

Greenport

8.6/10

Excellent

(585)

"Another amazing stay, even during a nor’easter. The staff did their best to still make the stay as enjoyable as it could have been with most things closed in the area. They were also kind enough to put us in the same room we had last time, which is our favorite thing about the Soundview and our trips out east. The view from our deck and the cute small things they have for dogs will keep us coming back. Thank you for another memorable trip. "

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

Stacie

CA $200

CA $298 total

includes taxes & fees

Nov 19 - Nov 20

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

![Exterior](https://images.trvl-media.com/lodging/5000000/4230000/4223700/4223615/948baf95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio | Living area](https://images.trvl-media.com/lodging/5000000/4230000/4223700/4223615/1ad86f14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio](https://images.trvl-media.com/lodging/5000000/4230000/4223700/4223615/6becca41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio | Living area](https://images.trvl-media.com/lodging/5000000/4230000/4223700/4223615/facf84c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### East Hampton House Resort

East Hampton North

9.0/10

Wonderful

(288)

"easy clean convenient beautiful grounds !!!"

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

carlo

CA $228

CA $291 total

includes taxes & fees

Nov 20 - Nov 21

[](https://www.expedia.ca/East-Hampton-Hotels-East-Hampton-House-Resort.h4223615.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/a27d78bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/39934cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/db00678f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/b026cb5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Econo Lodge Inn & Suites Old Saybrook Westbrook

Old Saybrook

7.2/10

Good

(457)

"the so-called breakfast was absolute minimum only thing available was make your own waffle"

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

Brian

CA $101

CA $116 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.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)

![Exterior](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/e70cf1f3.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)

### The Hampton Maid

Hampton Bays

9.0/10

Wonderful

(680)

"Love this place "

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

Diane

CA $398

CA $455 total

includes taxes & fees

Nov 15 - Nov 16

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/cd843dbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/98bad297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/42c9a535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/7fef8cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tower Inn And Suites Of Guilford - Madison

Guilford

7.4/10

Good

(230)

"excellent location to get to the beach"

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

claudia

CA $102

CA $118 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/New-Haven-Hotels-Tower-Inn-And-Suites-Of-Guilford-Madison.h1399998.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=2025-11-19&endDate=2025-11-20&regionId=183719&adults=2&lodging=CHALET&sort=RECOMMENDED&openPlayBack=true)

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

## Top Southold Hotel Reviews

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

### The Bentley Hotel Southampton

10/10 Excellent

"It was clean and the staff was very nice they "

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

![Budget Host East End Hotel in Riverhead](//images.trvl-media.com/lodging/2000000/1140000/1130500/1130479/ad0c5cd3_y.jpg)

### Budget Host East End Hotel in Riverhead

10/10 Excellent

"Very nice room for the price. Very clean, clean bed sheets, nice pillows and good mattress. Definitely will stay again."

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

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

### Sound View Greenport

10/10 Excellent

"We love the Sound View. We stay every year for a girls’ weekend. Rooms are great with a beautiful view. One thing the rooms could use are a standing closet for your clothes. Otherwise, it’s lovely."

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

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

### Saybrook Point Resort & Marina

10/10 Excellent

"This hotel has everything!!! We went for a girls’ night away, and we never had to leave. The heated pools and steam/sauna rooms were wonderful. The on-site restaurants and room service options were delicious. Our room was very clean and cozy, especially with the service of a staff member starting a fire for us in the fireplace. Every single staff member was incredibly helpful, friendly and hospitable, making the entire stay 5 stars! "

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

![The Sagaponack](//images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8_y.jpg)

### The Sagaponack

10/10 Excellent

"An all round lovely experience. Perfect location and attention to detail. Lovely layout and amenities. It was a peaceful stay. "

[](https://expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information)

![Madison Beach Hotel](//images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b_y.jpg)

### Madison Beach Hotel

10/10 Excellent

"yes"

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

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

### The Shoals Suites and Slips

10/10 Excellent

"Everything was Amazing! "

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

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

### Spark by Hilton Guilford

10/10 Excellent

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

[](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

10/10 Excellent

"Perfect "

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

## Find out more about Southold

## Southold Chalets information

| Number of reviews | 6,886 |
| --- | --- |
| Accommodation | 1 Chalets |
| Lowest Price | CA $116 |
| Highest Price | CA $1,651 |

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