A calm lake with a forest in the background during sunset.

Search Chalets in Southold from CA $152

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7
No exact matches found, but these alternatives could be just right

Recommended hotels in Southold

A storefront with a sign reading "THE SHOALS".

1. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (351 reviews)
"The shoals was a perfect place for our north fork adventures. The staff was very friendly and extremely accommodating! The location was beautiful and very relaxing."
United States
William
The price is CA $265
CA $338 total
includes taxes & fees
Nov 16 - Nov 17
The Shoals Suites and Slips
Property grounds

2. North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.

North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.
Southold
9.6 out of 10, Exceptional, (10 reviews)
"Overall we had a great stay, we weren’t in the apartment much and really only needed it for a place to stay at night. The space is the basement of a home with little natural sunlight. Overall it was ok for a weekend stay."
United States
Kelly V.
The price is CA $357
CA $675 total
includes taxes & fees
Nov 23 - Nov 24
North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.
The entrance to The Harbor Front Inn with a double door and the address number 209.

3. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
9.0 out of 10, Wonderful, (676 reviews)
"Clean and comfortable room. Great location to walk around town. Nice continental breakfast."
United States
Jessika
The price is CA $181
CA $248 total
includes taxes & fees
Dec 13 - Dec 14
The Harbor Front Inn
A restaurant with a signboard listing its hours of operation.

4. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (449 reviews)
"Great place to stay for a walkable visit to Greenport NY. Comfy bed, great rooms for hanging out, close to everything."
United States
JoAnn
The price is CA $222
CA $254 total
includes taxes & fees
Dec 16 - Dec 17
Zey Hotel
A lakeside patio with outdoor seating and a view of the water.

5. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (193 reviews)
"Amazing place to stay with a great location. We will definitely be back!"
United States
Kathleen
The price is CA $295
CA $337 total
includes taxes & fees
Dec 1 - Dec 2
Silver Sands Motel & Beach Bungalows
A coastal building with large windows, a deck, and a view of the sea at sunset.

6. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (768 reviews)
"The ambience is amazing! We loved our stay!!"
United States
Christine
The price is CA $212
CA $283 total
includes taxes & fees
Dec 14 - Dec 15
Sound View Greenport
A large, multi-story building with a porch and outdoor seating area, featuring multiple windows and a balcony.

7. The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (78 reviews)
"We enjoyed our stay!"
Australia
Nicholas
The price is CA $244
CA $279 total
includes taxes & fees
Nov 19 - Nov 20
The Chequit
A cozy interior with a bar area, seating, and a fireplace.

8. Oyster Estate

Oyster Estate
4.0 star property
Greenport
9.2 out of 10, Wonderful, (302 reviews)
"convenient location, clean & updated room. great stay :)"
United States
Jacqueline
The price is CA $257
CA $324 total
includes taxes & fees
Dec 2 - Dec 3
Oyster Estate
A house with a porch, a sign reading "House on Chase Creek," and a tree with red leaves.

9. House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (87 reviews)
"Such a cute place to stay! Bill was super kind and helpful! I was only in for a quick night but I would definitely stay here again!!"
United States
Tracey
The price is CA $264
CA $301 total
includes taxes & fees
Nov 16 - Nov 17
House on Chase Creek
A balcony with a view of the ocean, a lawn, and a house in the background.

10. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (300 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is CA $274
CA $471 total
includes taxes & fees
Nov 26 - Nov 27
Cliffside Resort Condominiums
A white outdoor seating area with a white table and a potted plant.

11. The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (619 reviews)
"great spot to stay,"
United States
Armando
The price is CA $168
CA $192 total
includes taxes & fees
Nov 22 - Nov 23
The Bentley Hotel Southampton
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

12. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is CA $445
CA $508 total
includes taxes & fees
Nov 16 - Nov 17
North Fork Resort
A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.

13. Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.4 out of 10, Very good, (847 reviews)
"Beautiful hotel vintage"
United States
Dennis
The price is CA $133
CA $152 total
includes taxes & fees
Nov 16 - Nov 17
Shorewood Inn
A building with a brick facade, a porch with steps, an American flag, and a sign with a ship and text.

14. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (689 reviews)
"The room was nicely appointed; sufficient parking; close to downtown; and a nice variety for breakfast."
United States
Annie
The price is CA $313
CA $357 total
includes taxes & fees
Nov 16 - Nov 17
Sag Harbor Inn
A rooftop deck with outdoor seating, fire pits, and a view of a body of water.

15. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (197 reviews)
"Very clean, excellent staff and excellent location. All of the shops and restaurants are within walking distance, and the wineries a very short cab ride. Really enjoyed staying here and we will absolutely be back."
United States
Daniel
The price is CA $363
CA $479 total
includes taxes & fees
Dec 14 - Dec 15
The Menhaden
A building with a red facade, a green tree in front, and a sign reading "OPENSPACE".

16. American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (208 reviews)
"Great location, very friendly and helpful "
United States
Mary
The price is CA $341
CA $446 total
includes taxes & fees
Nov 16 - Nov 17
American Beech Hotel
A building with a black front door, a balcony with railings, a street lamp above the door, and a sign that reads 'FARWAY.'

17. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (322 reviews)
"Great location , wonderful lobby bar Cute rooms"
United States
Thomas
The price is CA $417
CA $523 total
includes taxes & fees
Dec 16 - Dec 17
Faraway Sag Harbor
A two-story house with a balcony, a patio with outdoor furniture, and a fenced backyard.

18. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (58 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is CA $136
CA $346 total
includes taxes & fees
Nov 30 - Dec 1
The SandPiper
A metal compass sign with the words "AQUA VISTA GREENPORT" on a building's exterior wall.

19. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (54 reviews)
"Great property and location. So easily walkable to everything. The host was super responsive, we had a great stay!"
United States
Carey D.
The price is CA $136
CA $344 total
includes taxes & fees
Nov 18 - Nov 19
Aqua Vista
A deck with blue and white chairs, a table, and a striped umbrella.

20. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (29 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is CA $122
CA $329 total
includes taxes & fees
Nov 22 - Nov 23
Harbor Heights
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.
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Top Southold Hotel Reviews

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

8/10 Good
"The location of this hotel was excellent. It is close to many restaurants. Easy to get an Uber/Lyft. The clerk at the reception was knowledgeable and friendly. The room was clean. The breakfast was good. The hotel needs some updating which they are in the process of doing and that is why I gave it 4 stars overall."
Kerry 1-night trip
Posted 9 hours ago
Quality Inn Old Saybrook - Westbrook

Find out more about Southold

Southold Chalets information

Number of reviews
2,646
Accommodation
1 Chalets
Lowest Price
CA $152
Highest Price
CA $523

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