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Find hotels in Southold, NY from ￥14,224

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Dec 14 - Dec 15
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Dec 15 - Dec 16
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Dec 19 - Dec 21
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Dec 26 - Dec 28

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Our top choices for Southold hotels

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

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (228)
"Food!"
United States
Ryan
The price is ￥26,590
￥30,379 total
includes taxes & fees
Dec 17 - Dec 18
The Shoals Suites and Slips
Interior entrance
Vine & Sand

Vine & Sand

Vine & Sand
3.0 star property
Southold
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
Vine & Sand
Reception
Spark by Hilton Guilford

Spark by Hilton Guilford

Spark by Hilton Guilford
2.5 star property
Guilford
8.8 out of 10, Excellent, (65)
"Good clean property with great staff "
United States
David
The price is ￥15,717
￥18,074 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Spark by Hilton Guilford
Standard Studio, 1 King Bed, Non Smoking | Premium bedding, free WiFi, bed sheets
The Niantic Inn

The Niantic Inn

The Niantic Inn
2.5 star property
Niantic
9.2 out of 10, Wonderful, (128)
"Easy parking. Walkable dining and to boardwalk. Quaint shopping."
United States
Kerry
The price is ￥12,368
￥14,224 total
includes taxes & fees
Dec 15 - Dec 16
The Niantic Inn
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (442)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is ￥13,883
￥17,943 total
includes taxes & fees
Dec 15 - Dec 16
Hamlet Inn
Property grounds
Pier Blue Inn Old Saybrook - Essex

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, (1002)
"A welcoming place with some nice touches."
United States
Leslie
Pier Blue Inn Old Saybrook - Essex
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

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, (460)
"🙂"
United States
Jared
The price is ￥10,444
￥12,010 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
Property grounds
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (297)
"Great staff and clean rooms"
United States
Tyler
The price is ￥12,153
￥13,976 total
includes taxes & fees
Dec 15 - Dec 16
Clinton Motel
View from property
House on Chase Creek

House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
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
The price is ￥16,224
￥18,538 total
includes taxes & fees
Jan 6 - Jan 7, 2026
House on Chase Creek
Terrace/patio
Shorewood Inn

Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.6 out of 10, Excellent, (709)
"Couldn't have been easier! The woman at the front desk was warm and welcoming, the room was super clean and cute with the heat turned on full blast in anticipation of my arrival. Adorable backyard with seating, too. Super hot water in the shower. Perfect for an impromptu winter getaway. "
United States
Mahlon
Shorewood Inn
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (547)
"Awesome stay!!! Great Location "
United States
Bryan
The price is ￥20,894
￥31,498 total
includes taxes & fees
Dec 15 - Dec 16
The Harbor Front Inn
Indoor pool, open 9:00 AM to 9:00 PM, sun loungers
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1003)
"Staff was kind. Easy, comfortable stay."
United States
Jake
The price is ￥15,760
￥18,125 total
includes taxes & fees
Dec 21 - Dec 22
Quality Inn Old Saybrook - Westbrook
Property grounds
Liberty Inn

Liberty Inn

Liberty Inn
2.0 star property
Old Saybrook
7.4 out of 10, Good, (640)
"Great little place to stay with friendly staff and clean room"
United States
Carolan
The price is ￥12,480
￥14,352 total
includes taxes & fees
Dec 15 - Dec 16
Liberty Inn
Exterior
Tower Inn And Suites Of Guilford - Madison

Tower Inn And Suites Of Guilford - Madison

Tower Inn And Suites Of Guilford - Madison
2.5 star property
Guilford
7.4 out of 10, Good, (233)
"Clean, convenient, quiet place run by nice folks. We’d stay here again."
United States
Lisa
The price is ￥13,943
￥16,034 total
includes taxes & fees
Dec 15 - Dec 16
Tower Inn And Suites Of Guilford - Madison
Indoor pool, outdoor pool
Hyatt Place Long Island East End

Hyatt Place Long Island East End

Hyatt Place Long Island East End
3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1002)
"Our room had a great view of the river and marina. we also loved the seating area in the room. Very comfortable"
United States
Helen
The price is ￥18,074
￥20,651 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Hyatt Place Long Island East End
Exterior
The Sagaponack

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (213)
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is ￥23,462
￥33,035 total
includes taxes & fees
Dec 15 - Dec 16
The Sagaponack
Exterior
American Beech Hotel

American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
8.8 out of 10, Excellent, (195)
"The property was clean beautiful and pleasant. Loved the trendy decor."
United States
Jennifer
The price is ￥27,890
￥38,097 total
includes taxes & fees
Dec 15 - Dec 16
American Beech Hotel
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (396)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is ￥19,496
￥22,431 total
includes taxes & fees
Dec 21 - Dec 22
The Bentley Hotel Southampton
Exterior
Holiday Inn Express Hotel & Suites Long Island-East End by IHG

Holiday Inn Express Hotel & Suites Long Island-East End by IHG

Holiday Inn Express Hotel & Suites Long Island-East End by IHG
2.5 star property
Riverhead
8.6 out of 10, Excellent, (1003)
"Nice room. Good breakfast. Nice lobby and breakfast area. "
United States
Richard
The price is ￥16,672
￥19,047 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express Hotel & Suites Long Island-East End by IHG
Seasonal outdoor pool, pool umbrellas, sun loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (598)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is ￥26,355
￥37,736 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Sound View Greenport
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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Stay near popular Southold attractions

Sparkling Pointe

4.5/5 (2 reviews)
Sparkling Pointe crafts exquisite sparkling wines using traditional Méthode Champenoise in their Southold vineyard. Savor their diverse bubblies in an elegant tasting room with vineyard views.
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The Old Field Vineyards

4.0/5 (1 review)
This family-owned vineyard, Long Island's oldest continuously operated winery, offers handcrafted wines in a rustic setting. Enjoy tastings on expansive lawns overlooking Southold Bay.
See properties

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.

See all hotels in Southold
Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod.
Photo by Benny Goh
Open Photo by Benny Goh

Top Southold Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Holiday family tradition!"
Donald 1-night trip
Posted 2 days ago
Water's Edge Resort & Spa

More cheap stays in Southold

Budget Host East End Hotel in Riverhead

Budget Host East End Hotel in Riverhead

30 Lake Avenue Riverhead NY
The price is ￥14,584 per night from Dec 15 to Dec 16
￥14,584
￥16,663 total
Dec 15 - Dec 16
includes taxes & fees
6.6/10 (779 reviews)

Frequently asked questions

Where is the best place to stay in Southold?
The Shoals Suites and Slips is one of the top choices for your stay based on our traveler data. This hotel offers private balconies and a bar. Other good choices for your trip to the area are Pier Blue Inn Old Saybrook - Essex and Water's Edge Resort & Spa. See all available top hotels, or vacation rentals in Southold.
What's the top vacation rental in Southold?
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr: This vacation home rental outside of Southold offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. See all vacation rentals in Southold.
If I need to cancel my hotel reservation in Southold, will I receive a refund?
Yes, the majority of room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If your reservation is non-refundable, you might still have the option to cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Southold.
Where can I learn more about changing or cancelling my trip to Southold?
To access more information about rescheduling or cancelling your trip to Southold, head over to our customer service page.
What's the best pet-friendly accommodation in Southold?
White Blossom House Inn is a top hotel for people traveling with their pets, and offers free use of bicycles and in-room kitchens for its human guests. See more pet-friendly hotel accommodations in Southold.
Where is the best hotel to stay near Sparkling Pointe?
White Blossom House Inn is one of the top choices for your stay based on our traveler data, and this hotel offers free parking and private patios. It's located just a short 0.9 mi (1.4 km) from Sparkling Pointe.
What about the best place to stay close to Mattebella Vineyards?
One of the top choices for your stay is White Blossom House Inn, located a short 0.7 mi (1.1 km) from Mattebella Vineyards, and this hotel offers free parking and private patios.
What are some accommodations with pools in Southold?
Water's Edge Resort & Spa: Features a seasonal outdoor pool, an indoor pool, and a private beach. Sound View Greenport and Saybrook Point Resort & Marina are a couple of other choices that feature an onsite pool. View all hotels with pools in Southold.
What's the best place to stay near John F. Kennedy International Airport (JFK)?
Holiday Inn Express Kennedy Airport is a popular hotel, featuring free breakfast and free WiFi. It's located a short 1.5 mi (2.5 km) from John F. Kennedy Intl. Airport. Other options near the airport are Fairfield Inn by Marriott JFK Airport and Radisson Hotel JFK Airport.
What's it like to stay in Southold?
Visitors can enjoy all that Southold has to offer including the wineries, beaches, and gardens. Tourists can also enjoy the city's football games and monuments. In Southold, there are 148 hotels and other accommodations to choose from. Find out more about Southold.
What should I see while I'm in Southold?
The picturesque setting of McCabe's Beach and Horton Lane Beach exemplify the area's natural beauty. A couple of additional sights to add to your agenda are Sparkling Pointe and The Old Field Vineyards. Check out what more to see and do in Expedia's Southold guide.
How should I get around Southold?
To see more of the larger area, hop aboard a train at Southold Station. If you want to venture out around the area, you may want a rental car in Southold for your journey.
What's the weather like in Southold?
The hottest months are usually August and July with an average temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Southold is 57 inches.

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