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

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27
No exact matches found, but these alternatives could be just right

Recommended hotels in Southold

A light blue bus with "THE SHOALS" written on the front, parked in a driveway with a house and garden in the background.

1. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (332 reviews)
"Loved everything about our stay!"
United States
Melissa
The price is CA $280
CA $355 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, (712 reviews)
"Great one night stay."
United States
Irene
The price is CA $308
CA $392 total
includes taxes & fees
Oct 1 - Oct 2
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, (393 reviews)
"Very excellent boutique hotel right on Main st. Beautiful garden for relaxing. Perfect location, friendly staff"
United States
shaun
The price is CA $234
CA $267 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, (163 reviews)
"This was my first time in the North fork and this hotel was a total surprise It was absolutely wonderful The accommodations the service the food everything was a delight and we cannot wait to come back"
United States
Sol
The price is CA $411
CA $469 total
includes taxes & fees
Sep 30 - Oct 1
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, (54 reviews)
"Everything was great ! Wish we had been there when restaurant was open."
United States
Kathleen
The price is CA $312
CA $356 total
includes taxes & fees
Sep 13 - Sep 14
The Chequit
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

6. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (645 reviews)
"My family visited this hotel and were very pleased with our decision. Right in the heart of Greenport and minute walk to everything. Will plan to stay here again."
United States
Michael
The price is CA $351
CA $441 total
includes taxes & fees
Oct 1 - Oct 2
The Harbor Front Inn
A house with a porch, a sign reading "House on Chase Creek," and a tree with red leaves.

7. 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 $340
CA $389 total
includes taxes & fees
Sep 29 - Sep 30
House on Chase Creek

8. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (290 reviews)
"Great place!"
United States
Christine
The price is CA $406
CA $587 total
includes taxes & fees
Sep 27 - Sep 28
Cliffside Resort Condominiums
A deck with outdoor seating, overlooking a body of water with a sunset view.

9. The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.4 out of 10, Exceptional, (113 reviews)
"Stunning hotel! Will def stay again!"
United States
Anna
The price is CA $740
CA $930 total
includes taxes & fees
Sep 7 - Sep 8
The Pridwin Hotel
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, (52 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is CA $412
CA $470 total
includes taxes & fees
Oct 1 - Oct 2
North Fork Resort
A motel with a sign indicating the entrance, a parking lot, and a flagpole with an American flag.

11. Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (333 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 $108
CA $125 total
includes taxes & fees
Sep 3 - Sep 4
Clinton Motel
A guesthouse named Pier Blue with a sign, a parking lot, and a building with a red awning.

12. 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, (1,000 reviews)
"Pleasant one night stay in our trek"
United States
Carolyn
The price is CA $127
CA $146 total
includes taxes & fees
Sep 22 - Sep 23
Pier Blue Inn Old Saybrook - Essex
A white outdoor seating area with a white table and a potted plant.

13. The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (573 reviews)
"nice room for the price in season"
United States
Frank
The price is CA $201
CA $264 total
includes taxes & fees
Sep 27 - Sep 28
The Bentley Hotel Southampton
A multi-story residential building with blue trim and large windows.

14. 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, (491 reviews)
"Had a pleasant stay. Bed was comfortable & slept great. I shall return"
United States
Kenneth
The price is CA $105
CA $121 total
includes taxes & fees
Sep 27 - Sep 28
Econo Lodge Inn & Suites Old Saybrook Westbrook
A house with a covered porch, a garden with various plants and flowers, and a 'OPEN' sign on the window.

15. Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (499 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 $176
CA $227 total
includes taxes & fees
Sep 29 - Sep 30
Hamlet Inn

16. Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (65 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 $439
CA $502 total
includes taxes & fees
Sep 7 - Sep 8
Shelter Island House
A hotel lobby with a sign reading 'Quality Inn by Choice Hotels.'

17. 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)
"staff is friendly and helpful breakfast had many options room was clean"
United States
Theresa
The price is CA $140
CA $161 total
includes taxes & fees
Sep 27 - Sep 28
Quality Inn Old Saybrook - Westbrook
A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.

18. Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.4 out of 10, Very good, (808 reviews)
"Close to all , great for a night or 2- priced right"
United States
KAREN
The price is CA $209
CA $239 total
includes taxes & fees
Sep 7 - Sep 8
Shorewood Inn
A building with a red facade, a green tree in front, and a sign reading "OPENSPACE".

19. American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (206 reviews)
"The hotel doesn’t reception doesn’t open till 9am. For early risers we had to leave the hotel just to get coffee. 9am is unheard of for a hotel"
United States
kerri
The price is CA $432
CA $549 total
includes taxes & fees
Sep 7 - Sep 8
American Beech Hotel
A rooftop deck with outdoor seating, fire pits, and a view of a body of water.

20. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (190 reviews)
"Staff was very accommodating and extremely nice, Great stay!"
United States
Lisa
The price is CA $608
CA $751 total
includes taxes & fees
Sep 17 - Sep 18
The Menhaden
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
"Everything was great. Breakfast is a highlight"
Cindy 1-night trip
Posted less than an hour ago
Hyatt Place Long Island East End

Find out more about Southold

Southold Villas information

Number of reviews
6,750
Accommodation
32 Villas
Lowest Price
CA $121
Highest Price
CA $930

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