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

Southold Chalets

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17
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
$254 nightly
The price is $286
Oct 1 - Oct 2
Total with taxes and fees
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
$248 nightly
The price is $283
Oct 26 - Oct 27
Total with taxes and fees
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
$169 nightly
The price is $193
Oct 12 - Oct 13
Total with taxes and fees
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
$267 nightly
The price is $304
Oct 12 - Oct 13
Total with taxes and fees
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
$200 nightly
The price is $228
Oct 5 - Oct 6
Total with taxes and fees
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
$333 nightly
The price is $380
Oct 25 - Oct 26
Total with taxes and fees
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
$215 nightly
The price is $246
Oct 26 - Oct 27
Total with taxes and fees
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
$215 nightly
The price is $246
Oct 5 - Oct 6
Total with taxes and fees
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, (820 reviews)
"Close to all , great for a night or 2- priced right"
United States
KAREN
$86 nightly
The price is $98
Oct 12 - Oct 13
Total with taxes and fees
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
$253 nightly
The price is $289
Oct 20 - Oct 21
Total with taxes and fees
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
$264 nightly
The price is $301
Oct 12 - Oct 13
Total with taxes and fees
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
$201 nightly
The price is $230
Oct 4 - Oct 5
Total with taxes and fees
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
$165 nightly
The price is $186
Sep 29 - Sep 30
Total with taxes and fees
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
$374 nightly
The price is $421
Sep 29 - Sep 30
Total with taxes and fees
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
$150 nightly
The price is $171
Oct 4 - Oct 5
Total with taxes and fees
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
$78 nightly
The price is $90
Sep 29 - Sep 30
Total with taxes and fees
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
$78 nightly
The price is $90
Sep 29 - Sep 30
Total with taxes and fees
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
$67 nightly
The price is $77
Oct 25 - Oct 26
Total with taxes and fees
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
$69 nightly
The price is $79
Sep 29 - Sep 30
Total with taxes and fees
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
$107 nightly
The price is $123
Oct 4 - Oct 5
Total with taxes and fees
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

Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Great short weekend trip with me and my wife for a wedding! Great staff! Great little gym, great breakfast. Didn’t use the pools. Walking distance to other bars and restaurants. Would stay here again for sure!"
Howard 2-night trip
Posted 2 hours ago
Hyatt Place Long Island East End

Find out more about Southold

Southold Chalets information

Number of reviews
5,849
Accommodation
1 Chalets
Lowest Price
$77
Highest Price
$421

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