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 modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

1. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (334 reviews)
"Loved everything about our stay!"
United States
Melissa
The price is CA $279
CA $354 total
includes taxes & fees
Oct 1 - Oct 2
The Shoals Suites and Slips
A two-story house with a balcony, outdoor seating area, and a variety of plants.

2. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (397 reviews)
"Great location…thoroughly enjoyed our time."
United States
Renee
The price is CA $234
CA $267 total
includes taxes & fees
Sep 15 - Sep 16
Zey Hotel
A spacious room with wicker furniture, large windows, and a view of the sea.

3. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (714 reviews)
"Great one night stay."
United States
Irene
The price is CA $368
CA $460 total
includes taxes & fees
Oct 1 - Oct 2
Sound View Greenport
An outdoor patio area with string lights, tables, chairs, and a fire pit.

4. The Chequit

The Chequit
3.0 star property
The Heights
9.2 out of 10, Wonderful, (55 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 $264
CA $301 total
includes taxes & fees
Oct 4 - Oct 5
The Chequit
A seaside dining area with tables, chairs, and umbrellas, overlooking a body of water.

5. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (165 reviews)
"I love this place"
United States
Sirikhwan
The price is CA $414
CA $473 total
includes taxes & fees
Oct 6 - Oct 7
Silver Sands Motel & Beach Bungalows
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
9.0 out of 10, Wonderful, (649 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 $331
CA $418 total
includes taxes & fees
Oct 4 - Oct 5
The Harbor Front Inn
A serene landscape with a calm body of water reflecting trees with autumn foliage.

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 $298
CA $340 total
includes taxes & fees
Oct 5 - Oct 6
House on Chase Creek

8. 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 $278
CA $318 total
includes taxes & fees
Oct 4 - Oct 5
Shelter Island House
A modern house with a deck, outdoor seating, and a fire pit.

9. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (53 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is CA $415
CA $474 total
includes taxes & fees
Sep 30 - Oct 1
North Fork Resort

10. 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 $404
CA $585 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.

11. The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.4 out of 10, Exceptional, (114 reviews)
"Stunning hotel! Will def stay again!"
United States
Anna
The price is CA $737
CA $926 total
includes taxes & fees
Sep 7 - Sep 8
The Pridwin Hotel
A parking lot with a building in the background.

12. 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 $124 total
includes taxes & fees
Sep 14 - Sep 15
Clinton Motel
A sign for Pier Blue Guesthouse with a logo and name.

13. 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, (1,008 reviews)
"Pleasant one night stay in our trek"
United States
Carolyn
The price is CA $114
CA $131 total
includes taxes & fees
Sep 7 - Sep 8
Pier Blue Inn Old Saybrook - Essex
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.

14. The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (575 reviews)
"nice room for the price in season"
United States
Frank
The price is CA $207
CA $271 total
includes taxes & fees
Sep 27 - Sep 28
The Bentley Hotel Southampton
A glass-top table with a vase of flowers, surrounded by white-covered chairs, in a bright indoor setting with plants and a fireplace in the background.

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 $175
CA $227 total
includes taxes & fees
Sep 27 - Sep 28
Hamlet Inn
A modern hotel room with a large bed, a framed picture on the wall, and a wooden floor.

16. Hampton Bays Hotel on Main

Hampton Bays Hotel on Main
2.0 star property
Hampton Bays
7.6 out of 10, Good, (106 reviews)
"Property was new and excellently maintained. Confusing check-in for less computer savvy seniors. No parking a big bummer. Excellent downtown location. We would recommend with these considerations."
United States
Deborah
The price is CA $154
CA $176 total
includes taxes & fees
Sep 24 - Sep 25
Hampton Bays Hotel on Main
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.

17. American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (206 reviews)
"Great location, very friendly and helpful "
United States
Mary
The price is CA $430
CA $547 total
includes taxes & fees
Sep 21 - Sep 22
American Beech Hotel
An outdoor seating area with Adirondack chairs and a table, surrounded by American flags and flowers, with a view of houses and a body of water in the background.

18. Ocean View Terrace Inn

Ocean View Terrace Inn
2.0 star property
Hampton Bays
8.6 out of 10, Excellent, (134 reviews)
"Loved the place , I highly recommend staying there , the staff especially Stephanie so kind and helpful!! !"
United States
Sally
The price is CA $190
CA $298 total
includes taxes & fees
Sep 10 - Sep 11
Ocean View Terrace Inn
A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.

19. 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 $119
CA $136 total
includes taxes & fees
Sep 7 - Sep 8
Shorewood Inn
A conservatory with a sofa, chairs, a small table, and a view of houses.

20. The Penny Lane

The Penny Lane
3.0 star property
Hampton Bays
9.0 out of 10, Wonderful, (113 reviews)
"Clean and quiet stay"
United States
John
The price is CA $202
CA $231 total
includes taxes & fees
Oct 1 - Oct 2
The Penny Lane
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

Zey Hotel

Zey Hotel

10/10 Excellent
"The manager, James was so helpful during our stay. We loved that there was parking and a lovely home base during our getaway in Greenport. We loved the Zen feel, garden and lounge where we could read and relax during our stay. Our room was cozy and cool!"
Victoria 2-night trip
Posted 13 hours ago
Zey Hotel

Find out more about Southold

Southold Condo Resorts information

Number of reviews
4,188
Accommodation
0 Condo Resorts
Lowest Price
CA $124
Highest Price
CA $926

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