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Southold Condominium Resorts to Rent

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Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Condo Resorts in Southold

No exact matches found, but these alternatives could be just right

Recommended hotels in Southold

Garden Suite King | Premium bedding, down comforters, individually decorated
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 star property
9.6 out of 10, Exceptional, (226)
"Food!"
United States
Ryan
$174 nightly
The price is $199
Dec 29 - Dec 30
Total with taxes and fees
The Shoals Suites and Slips
Interior entrance
Vine & Sand

Bed & Breakfast in Southold

3.0 star property
9.6 out of 10, Exceptional, (13)
"This B&B, and its hosts, were simply amazing. I cannot recommend this place enough."
United States
Sandra
$320 nightly
The price is $366
Dec 16 - Dec 17
Total with taxes and fees
Vine & Sand
Interior
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Bed & Breakfast in Southold

10.0 out of 10, Exceptional, (1)
"Must like historical houses and little sausage-shaped dogs. A seamless blend of old and mod. Room is meticulously shiny clean. Substantial bedding designed for a good night’s sleep. High-end details (furnishings, footed tub with heat lamp and fluffy robes), culture (gallery), included breakfast is simple perfection due to high-quality ingredients/sourcing (fresh pastries, eggs, butter, fruit). Pool and hot tub divine. Our hosts are upbeat and fun and really went beyond for us. There are great...
United States
Jessica P.
$403 nightly
The price is $460
Jan 1 - Jan 2, 2026
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Interior
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Bed & Breakfast in Southold

10.0 out of 10, Exceptional, (1)
"Great experience. Wonderful hosts. "
United States
Mark L.
$367 nightly
The price is $420
Jan 1 - Jan 2, 2026
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Exterior
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Bed & Breakfast in Southold

$367 nightly
The price is $420
Jan 1 - Jan 2, 2026
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Interior
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Bed & Breakfast in Southold

$403 nightly
The price is $460
Jan 1 - Jan 2, 2026
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Reception
Spark by Hilton Guilford

Spark by Hilton Guilford

2.5 star property
8.8 out of 10, Excellent, (64)
"Good clean property with great staff "
United States
David
$101 nightly
The price is $116
Jan 3 - Jan 4, 2026
Total with taxes and fees
Spark by Hilton Guilford
Standard Studio, 1 King Bed, Non Smoking | Premium bedding, free WiFi, bed sheets
The Niantic Inn

The Niantic Inn

2.5 star property
9.2 out of 10, Wonderful, (126)
"Easy parking. Walkable dining and to boardwalk. Quaint shopping."
United States
Kerry
$98 nightly
The price is $113
Dec 15 - Dec 16
Total with taxes and fees
The Niantic Inn
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Motel in Southampton

2.0 star property
8.6 out of 10, Excellent, (440)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
$114 nightly
The price is $128
Dec 9 - Dec 10
Total with taxes and fees
Hamlet Inn
View from property
House on Chase Creek

Guesthouse in The Heights

2.5 star property
9.4 out of 10, Exceptional, (79)
" This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! "
United States
Maureen
$104 nightly
The price is $119
Jan 6 - Jan 7, 2026
Total with taxes and fees
House on Chase Creek
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2.0 star property
9.6 out of 10, Exceptional, (391)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
$118 nightly
The price is $135
Dec 11 - Dec 12
Total with taxes and fees
The Bentley Hotel Southampton
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn

The Harbor Front Inn

3.5 star property
8.8 out of 10, Excellent, (544)
"Awesome stay!!! Great Location "
United States
Bryan
$153 nightly
The price is $175
Dec 22 - Dec 23
Total with taxes and fees
The Harbor Front Inn
Property grounds
Clinton Motel

Motel in Clinton

2.5 star property
8.6 out of 10, Excellent, (296)
"Great staff and clean rooms"
United States
Tyler
$78 nightly
The price is $90
Dec 9 - Dec 10
Total with taxes and fees
Clinton Motel
Property grounds
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2.0 star property
8.0 out of 10, Very Good, (1001)
"A welcoming place with some nice touches."
United States
Leslie
$79 nightly
The price is $91
Dec 21 - Dec 22
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

Motel in Old Saybrook

2.0 star property
7.2 out of 10, Good, (460)
"🙂"
United States
Jared
$67 nightly
The price is $77
Dec 15 - Dec 16
Total with taxes and fees
Econo Lodge Inn & Suites Old Saybrook Westbrook
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$171 nightly
The price is $193
Jan 2 - Jan 3, 2026
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
Terrace/patio
Shorewood Inn

Motel in Riverhead

2.5 star property
8.4 out of 10, Very Good, (708)
"Bed was very comfortable.. staff was very friendly.. loud traffic in AM.. good water pressure.. would stay here again. "
United States
Shelly
$93 nightly
The price is $106
Dec 22 - Dec 23
Total with taxes and fees
Shorewood Inn
Indoor pool, open 9:00 AM to 9:00 PM, sun loungers
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 star property
7.8 out of 10, Good, (1002)
"Staff was kind. Easy, comfortable stay."
United States
Jake
$101 nightly
The price is $116
Dec 15 - Dec 16
Total with taxes and fees
Quality Inn Old Saybrook - Westbrook
Exterior
Aqua by American Beech - Adults Only

Aqua by American Beech - Adults Only

2.5 star property
9.4 out of 10, Exceptional, (312)
"Relaxing stay"
United States
Kristin
$160 nightly
The price is $182
Dec 9 - Dec 10
Total with taxes and fees
Aqua by American Beech - Adults Only
Terrace/patio
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

3.0 star property
8.6 out of 10, Excellent, (1003)
"Staff was courteous and the room was spotless. Food service is very good as well. "
United States
Efrem
$103 nightly
The price is $118
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hilton Garden Inn Riverhead
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

The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Yes"
Ray 1-night trip
Posted 5 hours ago
The Harbor Front Inn

Find out more about Southold

Southold Condo Resorts information

Number of reviews
6,653
Accommodation
0 Condo Resorts
Lowest Price
$77
Highest Price
$460

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