Photo by Benny Goh

Southold hotels from RM307

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8 Dec - 9 Dec
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9 Dec - 10 Dec
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12 Dec - 14 Dec
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19 Dec - 21 Dec

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Top 10 trending Southold hotels

Premium bedding, down duvets, individually decorated
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 star property
Southold
9.6 out of 10, Exceptional, (226)
"Food!"
United States
Ryan
The price is RM763
RM871 total
includes taxes & fees
9 Dec - 10 Dec
The Shoals Suites and Slips
Interior entrance
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
Exterior
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1001)
"Excellent food, in addition to friendly and helpful staff."
United States
marybeth
The price is RM1,271
RM1,564 total
includes taxes & fees
9 Dec - 10 Dec
Saybrook Point Resort & Marina
Exterior
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1001)
"Yes! Ease of registration! The staff helped us with dinning suggestions, hotel programs and amenities!"
United States
Bruce
The price is RM848
RM1,046 total
includes taxes & fees
9 Dec - 10 Dec
Water's Edge Resort & Spa
In-room safe, individually decorated, individually furnished, desk
Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

2.0 star property
Hampton Bays
7.2 out of 10, Good, (69)
"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"
United States
Olivia
Hampton Bays Hotel on Main
Property grounds
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, (1001)
"A welcoming place with some nice touches."
United States
Leslie
Pier Blue Inn Old Saybrook - Essex
Exterior
Madison Beach Hotel

Madison Beach Hotel

4.0 star property
Madison Center
9.4 out of 10, Exceptional, (339)
"The Spa was wonderful and the staff was attentive and helpful. "
United States
Emma
The price is RM995
RM1,144 total
includes taxes & fees
1 Jan - 2 Jan 2026
Madison Beach Hotel
Front of property
The Preston House & Hotel

The Preston House & Hotel

3.5 star property
Riverhead
9.8 out of 10, Exceptional, (371)
"Staff was amazing, include the restaurants’ staff! 2nd time staying there, will be back for many more!"
United States
Nakia
The price is RM769
RM879 total
includes taxes & fees
21 Dec - 22 Dec
The Preston House & Hotel
View from room
The Harbor Front Inn

The Harbor Front Inn

3.5 star property
Greenport
8.8 out of 10, Excellent, (543)
"Awesome stay!!! Great Location "
United States
Bryan
The price is RM539
RM817 total
includes taxes & fees
29 Dec - 30 Dec
The Harbor Front Inn
Terrace/patio
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

3.0 star property
Riverhead
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
The price is RM424
RM485 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hilton Garden Inn Riverhead
Outdoor pool
The Atlantic Hotel

The Atlantic Hotel

2.5 star property
Southampton
7.2 out of 10, Good, (974)
"Great hotel for a quick stay - very friendly staff"
United States
Dianne
The Atlantic Hotel
Exterior
Zey Hotel

Zey Hotel

3.5 star property
Greenport
9.2 out of 10, Wonderful, (290)
"Loved this place. Lots of places to relax and play games. Super-friendly staff. Can't wait to go back b"
United States
Susie
Zey Hotel
Property amenity
Residence Inn by Marriott New York Long Island East End

Residence Inn by Marriott New York Long Island East End

3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1002)
"Great staff, very clean and modern facility, nicely appointed rooms, and a lot of things nearby to do."
United States
Mary J
The price is RM509
RM582 total
includes taxes & fees
4 Jan - 5 Jan 2026
Residence Inn by Marriott New York Long Island East End
Indoor pool, open 9:00 AM to 9:00 PM, pool loungers
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 star property
Old Saybrook
7.8 out of 10, Good, (1002)
"Staff was kind. Easy, comfortable stay."
United States
Jake
The price is RM416
RM478 total
includes taxes & fees
14 Dec - 15 Dec
Quality Inn Old Saybrook - Westbrook
Property grounds
The Hampton Maid

The Hampton Maid

2.5 star property
Hampton Bays
9.0 out of 10, Wonderful, (688)
"Great place to stay"
United States
Mitchell
The price is RM1,166
RM1,332 total
includes taxes & fees
12 Dec - 13 Dec
The Hampton Maid
Exterior
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, (1002)
"It was a nice hotel and it was clean "
United States
Shaquan
The price is RM374
RM428 total
includes taxes & fees
21 Dec - 22 Dec
Holiday Inn Express Hotel & Suites Long Island-East End by IHG
Desk, laptop workspace, blackout curtains, iron/ironing board
Greenview Inn Riverhead

Greenview Inn Riverhead

2.0 star property
Riverhead
7.4 out of 10, Good, (781)
"Nice staff Beautiful & Safe place "
United States
Cameron
Greenview Inn Riverhead
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

2.0 star property
Southampton
8.6 out of 10, Excellent, (440)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is RM366
RM474 total
includes taxes & fees
9 Dec - 10 Dec
Hamlet Inn
Reception
Spark by Hilton Guilford

Spark by Hilton Guilford

2.5 star property
Guilford
8.8 out of 10, Excellent, (64)
"Good clean property with great staff "
United States
David
The price is RM405
RM466 total
includes taxes & fees
3 Jan - 4 Jan 2026
Spark by Hilton Guilford
Outdoor pool
Sag Harbor Inn

Sag Harbor Inn

3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (572)
"Very clean, helpful staff and convenient location."
United States
Gordon
The price is RM884
RM1,010 total
includes taxes & fees
9 Dec - 10 Dec
Sag Harbor 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.
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Stay near popular Southold attractions

Sparkling Pointe

4.5/5 (2 reviews)
You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area.
See properties

The Old Field Vineyards

4.0/5 (1 review)
You can enjoy a tasting or tour at The Old Field Vineyards during your travels to Southold. Stroll along the beaches or discover the sunsets in this family-friendly area.
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
"Yes! Ease of registration! The staff helped us with dinning suggestions, hotel programs and amenities!"
Bruce 2-night trip
Posted 1 day ago
Water's Edge Resort & Spa

More cheap stays in Southold

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
Get rates
7.8/10 Good! (1,000 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 traveller data. This hotel offers private balconies and a bar. Other good choices for your stay in the area are Quality Inn Old Saybrook - Westbrook and Sound View Greenport. See all available top hotels, or vacation rentals in Southold.
If I need to cancel my hotel reservation in Southold, will I receive a refund?
Yes, most hotel bookings are fully refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Southold.
What's the best dog-friendly accommodation option in Southold?
White Blossom House Inn is a top hotel for people travelling 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.
What are some accommodation options with pools in Southold?
Quality Inn Old Saybrook - Westbrook: Offers buffet, an indoor pool and free self parking. Sound View Greenport and Saybrook Point Resort & Marina are a couple of other choices that offer an on-site pool. View all hotels with pools in Southold.
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 151 hotels and other accommodation options to choose from. Find out more about Southold.
What should I do while I'm visiting Southold?
The picturesque setting of Horton Lane Beach and McCabe's Beach exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are The Old Field Vineyards and Sparkling Pointe. Take a look at what more there is to see and do in Expedia's Southold guide.
What's the best way to 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 temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Southold is 1452 mm.

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