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

Southold Condominium Resorts to Rent

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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

Exterior

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
Exterior

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
$169 nightly
The price is $193
Sep 21 - Sep 22
Total with taxes and fees
Zey Hotel
Resort view

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
$295 nightly
The price is $337
Oct 6 - Oct 7
Total with taxes and fees
Sound View Greenport
Outdoor dining

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
$195 nightly
The price is $222
Oct 5 - Oct 6
Total with taxes and fees
The Chequit
Beach bar

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 21 - Sep 22
Total with taxes and fees
Silver Sands Motel & Beach Bungalows
Suite, 1 Bedroom, Terrace, Harbor View | Terrace/patio

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
$257 nightly
The price is $293
Oct 4 - Oct 5
Total with taxes and fees
The Harbor Front Inn
View from property

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
$215 nightly
The price is $246
Oct 5 - Oct 6
Total with taxes and fees
House on Chase Creek
Front of property - evening/night

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
$201 nightly
The price is $230
Oct 4 - Oct 5
Total with taxes and fees
Shelter Island House
Living area

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
$286 nightly
The price is $326
Sep 7 - Sep 8
Total with taxes and fees
North Fork Resort
Condo | Terrace/patio

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 27 - Sep 28
Total with taxes and fees
Cliffside Resort Condominiums
Terrace/patio

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
$586 nightly
The price is $669
Sep 7 - Sep 8
Total with taxes and fees
The Pridwin Hotel
Property grounds

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
$78 nightly
The price is $90
Sep 14 - Sep 15
Total with taxes and fees
Clinton Motel
Property grounds

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
$83 nightly
The price is $96
Sep 8 - Sep 9
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
Reception

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
$172 nightly
The price is $196
Sep 27 - Sep 28
Total with taxes and fees
The Bentley Hotel Southampton
Restaurant

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
$146 nightly
The price is $164
Sep 27 - Sep 28
Total with taxes and fees
Hamlet Inn
Deluxe Double Room, 1 King Bed, City View

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
$124 nightly
The price is $141
Sep 13 - Sep 14
Total with taxes and fees
Hampton Bays Hotel on Main
Terrace/patio

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
$346 nightly
The price is $395
Sep 21 - Sep 22
Total with taxes and fees
American Beech Hotel
Exterior

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
$194 nightly
The price is $215
Oct 4 - Oct 5
Total with taxes and fees
Ocean View Terrace Inn
Exterior

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
$98 nightly
The price is $112
Sep 7 - Sep 8
Total with taxes and fees
Shorewood Inn
Reception

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
$164 nightly
The price is $188
Oct 1 - Oct 2
Total with taxes and fees
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
$90
Highest Price
$669

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