Southold Condominium Resorts to Rent

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Recommended hotels in Southold

1. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (349 reviews)
"Very clean property, beautiful view, and quiet."
United States
Masayo
$210 nightly
The price is $237
Nov 22 - Nov 23
Total with taxes and fees
The Shoals Suites and Slips

2. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (766 reviews)
"The ambience is amazing! We loved our stay!!"
United States
Christine
$169 nightly
The price is $193
Dec 7 - Dec 8
Total with taxes and fees
Sound View Greenport

3. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
9.0 out of 10, Wonderful, (674 reviews)
"Such a lovely place for a getaway. Charming town and lovely water views!"
United States
Laura
$159 nightly
The price is $182
Nov 15 - Nov 16
Total with taxes and fees
The Harbor Front Inn

4. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (444 reviews)
"Great location…thoroughly enjoyed our time."
United States
Renee
$152 nightly
The price is $174
Nov 23 - Nov 24
Total with taxes and fees
Zey Hotel

5. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (187 reviews)
"Nicely renovated and enjoyable."
United States
Becky
$215 nightly
The price is $246
Dec 7 - Dec 8
Total with taxes and fees
Silver Sands Motel & Beach Bungalows

6. The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (76 reviews)
"Friendly staff , Unique property."
United States
Patrick
$166 nightly
The price is $190
Dec 2 - Dec 3
Total with taxes and fees
The Chequit

7. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
United States
William
$269 nightly
The price is $307
Nov 30 - Dec 1
Total with taxes and fees
Cliffside Resort Condominiums

8. House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (87 reviews)
"Such a cute place to stay! Bill was super kind and helpful! I was only in for a quick night but I would definitely stay here again!!"
United States
Tracey
$185 nightly
The price is $211
Nov 9 - Nov 10
Total with taxes and fees
House on Chase Creek

9. Oyster Estate

Oyster Estate
4.0 star property
Greenport
9.2 out of 10, Wonderful, (301 reviews)
"convenient location, clean & updated room. great stay :)"
United States
Jacqueline
$202 nightly
The price is $230
Dec 7 - Dec 8
Total with taxes and fees
Oyster Estate

10. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (686 reviews)
"The room was nicely appointed; sufficient parking; close to downtown; and a nice variety for breakfast."
United States
Annie
$219 nightly
The price is $250
Nov 8 - Nov 9
Total with taxes and fees
Sag Harbor Inn

11. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
$202 nightly
The price is $230
Nov 8 - Nov 9
Total with taxes and fees
Harbor Heights

12. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (57 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
$202 nightly
The price is $230
Nov 10 - Nov 11
Total with taxes and fees
The SandPiper

13. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (196 reviews)
"Very clean, excellent staff and excellent location. All of the shops and restaurants are within walking distance, and the wineries a very short cab ride. Really enjoyed staying here and we will absolutely be back."
United States
Daniel
$285 nightly
The price is $326
Dec 6 - Dec 7
Total with taxes and fees
The Menhaden

14. American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (208 reviews)
"Great location, very friendly and helpful "
United States
Mary
$286 nightly
The price is $327
Nov 10 - Nov 11
Total with taxes and fees
American Beech Hotel

15. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
$299 nightly
The price is $341
Nov 11 - Nov 12
Total with taxes and fees
North Fork Resort

16. The Atlantic Hotel

The Atlantic Hotel
2.5 star property
Southampton
7.2 out of 10, Good, (1,000 reviews)
"Lots of parking, rooms were clean and smelt nice"
United States
miranda
$129 nightly
The price is $147
Dec 7 - Dec 8
Total with taxes and fees
The Atlantic Hotel

17. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (52 reviews)
"Great location and nice spot."
United States
Kerri L.
$212 nightly
The price is $242
Nov 9 - Nov 10
Total with taxes and fees
Aqua Vista

18. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (320 reviews)
"Great location , wonderful lobby bar Cute rooms"
United States
Thomas
$303 nightly
The price is $346
Dec 7 - Dec 8
Total with taxes and fees
Faraway Sag Harbor

19. Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.4 out of 10, Very good, (843 reviews)
"Beautiful hotel vintage"
United States
Dennis
$93 nightly
The price is $106
Nov 20 - Nov 21
Total with taxes and fees
Shorewood Inn

20. Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (518 reviews)
"You can't find a nicer owner, or a more laid back conveniently located spot"
United States
Eric
$137 nightly
The price is $154
Nov 8 - Nov 9
Total with taxes and fees
Hamlet Inn
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.

Learn more about Southold

Vineyards and farm stands dot the landscape of this North Fork gem, inviting visitors to sample local wines and fresh produce. Stroll along the pebble beaches, explore historic lighthouses, or take a ferry to nearby Shelter Island for a day trip.

A coastal landscape with a white church on a grassy hill, overlooking a sandy beach and the ocean.

Top reviews in Southold

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