Southold Chalets

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17
No exact matches found, but these alternatives could be just right

Recommended hotels in Southold

Front of property

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (237 reviews)
"Great stay, will definitely go again"
United States
ANTONIO J
$157 nightly
The price is $180
Jan 26 - Jan 27
Total with taxes and fees
The Shoals Suites and Slips
Exterior

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (15 reviews)
"Wonderful stay"
United States
Judy
$324 nightly
The price is $371
Feb 1 - Feb 2
Total with taxes and fees
Vine & Sand
Exterior

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Southold
10.0 out of 10, Exceptional, (1 review)
"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.
$381 nightly
The price is $435
Jan 22 - Jan 23
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Exterior

Beautifully farmhouse

Beautifully farmhouse
Southold
10.0 out of 10, Exceptional, (3 reviews)
"good experience"
United States
Anonymous traveler
$1,028 nightly
The price is $1,175
Jan 22 - Jan 23
Total with taxes and fees
Beautifully farmhouse
Exterior

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Southold
10.0 out of 10, Exceptional, (1 review)
"Great experience. Wonderful hosts. "
United States
Mark L.
$349 nightly
The price is $399
Jan 27 - Jan 28
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

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Southold
$357 nightly
The price is $408
Jan 22 - Jan 23
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Exterior

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Southold
$381 nightly
The price is $435
Jan 22 - Jan 23
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Front of property

Spark by Hilton Guilford

Spark by Hilton Guilford
2.5 star property
Guilford
8.8 out of 10, Excellent, (83 reviews)
"The front desk staff were excellent, clean and comfortable stay."
United States
JUstine
$103 nightly
The price is $119
Jan 30 - Jan 31
Total with taxes and fees
Spark by Hilton Guilford
Exterior

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, (1,000 reviews)
"A welcoming place with some nice touches."
United States
Leslie
$79 nightly
The price is $91
Jan 22 - Jan 23
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
Free self parking

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (301 reviews)
"The room was comfortable and clean. A good value for the money."
United States
Michael
$76 nightly
The price is $87
Jan 26 - Jan 27
Total with taxes and fees
Clinton Motel
Exterior

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,003 reviews)
"Was a clean room and the pool was warm and kids had fun. Breakfast was good and plenty of choices "
United States
pieter
$97 nightly
The price is $111
Jan 28 - Jan 29
Total with taxes and fees
Quality Inn Old Saybrook - Westbrook
Golf

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (448 reviews)
"Room was in good condition however I found the shower to be extremely small despite having great water pressure and extremely nice temperature."
United States
gail
$110 nightly
The price is $124
Jan 22 - Jan 23
Total with taxes and fees
Hamlet Inn
Lunch, dinner, brunch served; American cuisine, beach views

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (607 reviews)
"Nice place"
United States
Mateusz
$143 nightly
The price is $164
Feb 16 - Feb 17
Total with taxes and fees
Sound View Greenport
One Bedroom Harbor View Terrace Suite | View from room

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (562 reviews)
"Everything was Great Immaculate hotel very good location sraff was great"
United States
latoya
$159 nightly
The price is $182
Jan 25 - Jan 26
Total with taxes and fees
The Harbor Front Inn
Exterior

Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.4 out of 10, Very Good, (717 reviews)
"ROOM WAS CLEAN, WARM, GOOD PARKING"
United States
JOSEPH
$92 nightly
The price is $105
Jan 22 - Jan 23
Total with taxes and fees
Shorewood Inn

House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (79 reviews)
" 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 22 - Jan 23
Total with taxes and fees
House on Chase Creek
Exterior

The Niantic Inn

The Niantic Inn
2.5 star property
Niantic
9.2 out of 10, Wonderful, (134 reviews)
"Quiet and warm and clean. Nice touch from Housekeeping too! "
United States
Jessica
$128 nightly
The price is $147
Jan 26 - Jan 27
Total with taxes and fees
The Niantic Inn
18 bedrooms, premium bedding, minibar, in-room safe

Aqua by American Beech - Adults Only

Aqua by American Beech - Adults Only
2.5 star property
Riverhead
9.4 out of 10, Exceptional, (312 reviews)
"Relaxing stay"
United States
Kristin
$201 nightly
The price is $229
Feb 4 - Feb 5
Total with taxes and fees
Aqua by American Beech - Adults Only
Exterior

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$188 nightly
The price is $210
Jan 22 - Jan 23
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
Exterior detail

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
Southampton
8.6 out of 10, Excellent, (206 reviews)
"Staff was amazing. The room was very clean. I've stayed here numerous times, even on the night before my wedding as I was married in the Hamptons and I highly recommend! "
United States
Martine
$110 nightly
The price is $125
Jan 22 - Jan 23
Total with taxes and fees
Southampton Long Island Hotel
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southold Hotel Reviews

The Preston House & Hotel

The Preston House & Hotel

10/10 Excellent
"Wonderful experience at the Preston. Inspite of the broken elevator the entire staff went out of their ways to make our stay top self Danielle the front desk person helped us with our bags and each morning helped to carry breakfast to the room. The bartender was delightful and very personable and made good driks. Famtastic time in a great hotel. Thanks to the entire staff."
cathleen 2-night trip
Posted 2 days ago
The Preston House & Hotel

Find out more about Southold

Southold Chalets information

Number of reviews
5,709
Accommodation
1 Chalets
Lowest Price
$87
Highest Price
$1,175

Explore a world of travel with Expedia