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

Southold Residences

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3
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
$227 nightly
The price is $256
Oct 1 - Oct 2
Total with taxes and fees
The Shoals Suites and Slips
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

2. Villa Luz Family Home w/ heated pool & jacuzzi

Villa Luz Family Home w/ heated pool & jacuzzi
Hampon Bays
9.6 out of 10, Exceptional, (26 reviews)
"Everything was in order. When there were a couple of very minor glitches, the manager of the property was immediately responsive - and glitch gone, fast. This was one of the smoothest VRBO experiences we've had, and we've had many."
United States
Carola C.
$1,584 nightly
The price is $1,679
Sep 9 - Sep 10
Total with taxes and fees
Villa Luz Family Home w/ heated pool & jacuzzi
A two-story house with a balcony, outdoor seating area, and a variety of plants.

3. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (398 reviews)
"Great location…thoroughly enjoyed our time."
United States
Renee
$169 nightly
The price is $193
Sep 23 - Sep 24
Total with taxes and fees
Zey Hotel
A spacious room with wicker furniture, large windows, and a view of the sea.

4. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (717 reviews)
"Great one night stay."
United States
Irene
$348 nightly
The price is $398
Sep 23 - Sep 24
Total with taxes and fees
Sound View Greenport
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
$295 nightly
The price is $338
Sep 30 - Oct 1
Total with taxes and fees
Silver Sands Motel & Beach Bungalows
An outdoor patio area with string lights, tables, chairs, and a fire pit.

6. The Chequit

The Chequit
3.0 star property
The Heights
9.2 out of 10, Wonderful, (55 reviews)
"Everything was great ! Wish we had been there when restaurant was open."
United States
Kathleen
$182 nightly
The price is $208
Oct 8 - Oct 9
Total with taxes and fees
The Chequit
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, (650 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
$259 nightly
The price is $296
Oct 4 - Oct 5
Total with taxes and fees
The Harbor Front Inn
A serene landscape with a calm body of water reflecting trees with autumn foliage.

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

9. 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

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
$370 nightly
The price is $423
Sep 30 - Oct 1
Total with taxes and fees
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

11. 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
$263 nightly
The price is $301
Sep 29 - Sep 30
Total with taxes and fees
North Fork Resort
A sign for Pier Blue Guesthouse with a logo and name.

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, (1,013 reviews)
"Pleasant one night stay in our trek"
United States
Carolyn
$95 nightly
The price is $109
Sep 10 - Sep 11
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
A deck with outdoor seating, overlooking a body of water with a sunset view.

13. The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.4 out of 10, Exceptional, (115 reviews)
"Stunning hotel! Will def stay again!"
United States
Anna
$558 nightly
The price is $637
Sep 13 - Sep 14
Total with taxes and fees
The Pridwin Hotel
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, (576 reviews)
"nice room for the price in season"
United States
Frank
$172 nightly
The price is $196
Sep 27 - Sep 28
Total with taxes and fees
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, (500 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
$146 nightly
The price is $164
Sep 27 - Sep 28
Total with taxes and fees
Hamlet Inn
A parking lot with a building in the background.

16. 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
$78 nightly
The price is $90
Sep 14 - Sep 15
Total with taxes and fees
Clinton Motel
A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.

17. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,011 reviews)
"staff is friendly and helpful breakfast had many options room was clean"
United States
Theresa
$101 nightly
The price is $116
Oct 4 - Oct 5
Total with taxes and fees
Quality Inn Old Saybrook - Westbrook
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.

18. 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
$304 nightly
The price is $347
Sep 9 - Sep 10
Total with taxes and fees
American Beech Hotel
A modern hotel room with a large bed, a framed picture on the wall, and a wooden floor.

19. 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
$107 nightly
The price is $122
Sep 24 - Sep 25
Total with taxes and fees
Hampton Bays Hotel on Main
A hotel room with a large bathtub, a desk with a lamp, a chair, and a bed with a red blanket.

20. 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, (495 reviews)
"It was a great place to stay Quiet and clean and staff was responsible"
United States
Laurie
$72 nightly
The price is $82
Oct 4 - Oct 5
Total with taxes and fees
Econo Lodge Inn & Suites 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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"This was one night, strictly for sleeping. It worked perfectly for that. Everything was clean, supplies were adequate, shower was hot and plentiful, the HVAC worked fine, the bed was comfortable, and it was quiet all night. Friendly, easy check-in, and check out. Good location for me with several choices for good restaurants for dinner and breakfast. I would be happy to return."
Michael B 1-night trip
Posted 1 hour ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Southold

Southold Residences information

Number of reviews
3,486
Accommodation
1 Residences
Lowest Price
$82
Highest Price
$637

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