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

Search Chalets in Southold from CA $109

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24
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, (342 reviews)
"Loved everything about our stay!"
United States
Melissa
The price is CA $285
CA $361 total
includes taxes & fees
Oct 1 - Oct 2
The Shoals Suites and Slips
A coastal building with large windows, a deck, and a view of the sea at sunset.

2. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (738 reviews)
"Great one night stay."
United States
Irene
The price is CA $322
CA $408 total
includes taxes & fees
Oct 26 - Oct 27
Sound View Greenport
A restaurant with a signboard listing its hours of operation.

3. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (411 reviews)
"Great location…thoroughly enjoyed our time."
United States
Renee
The price is CA $239
CA $273 total
includes taxes & fees
Sep 29 - Sep 30
Zey Hotel
A seaside dining area with tables, chairs, and umbrellas, overlooking a body of water.

4. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (170 reviews)
"Excellent stay. The room was clean and stylish. Can’t wait to come back"
United States
Sarah
The price is CA $400
CA $457 total
includes taxes & fees
Oct 12 - Oct 13
Silver Sands Motel & Beach Bungalows
A large, multi-story building with a porch and outdoor seating area, featuring multiple windows and a balcony.

5. The Chequit

The Chequit
3.0 star property
The Heights
9.2 out of 10, Wonderful, (64 reviews)
"It’s a beautiful property with a fun bar and delicious restaurant . The rooms were beautiful and the bed was super comfortable"
United States
Kristin
The price is CA $278
CA $318 total
includes taxes & fees
Oct 5 - Oct 6
The Chequit

6. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (295 reviews)
"Great place!"
United States
Christine
The price is CA $334
CA $538 total
includes taxes & fees
Oct 25 - Oct 26
Cliffside Resort Condominiums
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

7. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
9.0 out of 10, Wonderful, (660 reviews)
"Great location"
United States
Jordan
The price is CA $292
CA $374 total
includes taxes & fees
Oct 28 - Oct 29
The Harbor Front Inn
A house with a porch, a sign reading "House on Chase Creek," and a tree with red leaves.

8. House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (86 reviews)
"Nice owner.. convenient location"
United States
Calvin
The price is CA $304
CA $348 total
includes taxes & fees
Oct 5 - Oct 6
House on Chase Creek
A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.

9. Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.4 out of 10, Very good, (821 reviews)
"Close to all , great for a night or 2- priced right"
United States
KAREN
The price is CA $121
CA $138 total
includes taxes & fees
Sep 29 - Sep 30
Shorewood Inn
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

10. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (60 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is CA $373
CA $426 total
includes taxes & fees
Oct 26 - Oct 27
North Fork Resort
A building with a red facade, a green tree in front, and a sign reading "OPENSPACE".

11. American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (207 reviews)
"Great location, very friendly and helpful "
United States
Mary
The price is CA $324
CA $427 total
includes taxes & fees
Oct 1 - Oct 2
American Beech Hotel

12. Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (66 reviews)
"This boutique hotel is a true gem. Set among lush trees and beautiful landscaping, and with excellent indoor space, it provides a welcoming and relaxing atmosphere."
United States
Dorothy
The price is CA $285
CA $325 total
includes taxes & fees
Oct 4 - Oct 5
Shelter Island House
A large, traditional house with multiple chimneys, surrounded by a well-maintained lawn and a sand bunker.

13. Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (508 reviews)
"I loved staying here! Great location, great rooms, and the woman who runs it (Denise?) is so incredibly helpful in directing guests to the best beaches, restaurants, least traffic routes, activities. Will stay here many times in the future!"
United States
Thomas
The price is CA $179
CA $232 total
includes taxes & fees
Sep 29 - Sep 30
Hamlet Inn
A rooftop deck with outdoor seating, fire pits, and a view of a body of water.

14. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (191 reviews)
"Staff was very accommodating and extremely nice, Great stay!"
United States
Lisa
The price is CA $472
CA $595 total
includes taxes & fees
Sep 29 - Sep 30
The Menhaden
A white outdoor seating area with a white table and a potted plant.

15. The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (591 reviews)
"nice room for the price in season"
United States
Frank
The price is CA $177
CA $242 total
includes taxes & fees
Oct 4 - Oct 5
The Bentley Hotel Southampton
A motel with a large parking lot and multiple rooms.

16. Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (337 reviews)
"Hotel was clean and the staff was pleasant. The pool was wonderful! I would stay there again."
United States
Selena
The price is CA $110
CA $127 total
includes taxes & fees
Sep 29 - Sep 30
Clinton Motel
A guesthouse named Pier Blue with a sign, a parking lot, and a building with a red awning.

17. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
2.0 star property
Saybrook Manor
8.0 out of 10, Very good, (1,014 reviews)
"It was a decent stay, we came in for a family reunion and originally planning to camp but weren’t able to due to the storm so we found this last min at a decent price point. Staff was very friendly when we came in, seems to be family operated which I like. Room was clean could use some updates but I liked the almost beachy vibe they have."
United States
virginia
The price is CA $111
CA $127 total
includes taxes & fees
Sep 29 - Sep 30
Pier Blue Inn Old Saybrook - Essex
A multi-story residential building with blue trim and large windows.

18. Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
Old Saybrook
7.2 out of 10, Good, (498 reviews)
"It was a great place to stay Quiet and clean and staff was responsible"
United States
Laurie
The price is CA $95
CA $109 total
includes taxes & fees
Oct 25 - Oct 26
Econo Lodge Inn & Suites Old Saybrook Westbrook
A two-story motel with a symmetrical facade, multiple windows, and a parking lot in front.

19. Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
2.5 star property
Clinton
6.4 out of 10, (257 reviews)
"The Lamplighter is the place I always stay at when I am in this section of Connecticut. It has Clean Rooms, Comfortable Beds, Good Working Air-conditioning, plenty of Hot Water for the Shower, a Low Price, Friendly Staff, Microwaves and Refrigerators, close to the Highway, walking distance to a Great Restaurant ( the Log Cabin). I'm already looking forward to my Return."
United States
Steven
The price is CA $98
CA $112 total
includes taxes & fees
Sep 29 - Sep 30
Lamplighter Motel - Clinton, Connecticut
A hotel lobby with a sign reading 'Quality Inn by Choice Hotels.'

20. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,005 reviews)
"Great location, rooms were big and clean."
United States
Renee
The price is CA $151
CA $174 total
includes taxes & fees
Oct 4 - Oct 5
Quality Inn Old Saybrook - Westbrook
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

The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"Nice clean hotel in town"
Chris 2-night trip
Posted 6 hours ago
The Atlantic Hotel

Find out more about Southold

Southold Chalets information

Number of reviews
5,850
Accommodation
1 Chalets
Lowest Price
CA $109
Highest Price
CA $595

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