Photo by Benny Goh

Hotels in Southold

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Check prices for these dates

Tonight
Apr 28 - Apr 29
Tomorrow
Apr 29 - Apr 30
This weekend
May 1 - May 3
Next weekend
May 8 - May 10

Where to stay in Southold?

Exterior
The Shoals Suites and Slips
The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (265 reviews)
Dive into waterside charm at this Southold retreat on the bay. Located near The Old Field Vineyards and Crescent Beach, the hotel offers free WiFi, bicycles, and a cafe/bar lounge. Travelers consistently praise the helpful staff for enhancing their stay experience.
The price is $188
$240 total
includes taxes & fees
Apr 29 - Apr 30
The Shoals Suites and Slips
Interior
Vine & Sand
Vine & Sand
3.0 star property
Southold
9.8 out of 10, Exceptional, (16 reviews)
Soak in North Fork charm at this Southold B&B near Croteaux Vineyards. Enjoy the seasonal outdoor pool, complimentary buffet breakfast, and free bike rentals to explore wine country. The garden and terrace offer peaceful retreats after vineyard adventures.
The price is $361
$412 total
includes taxes & fees
Apr 29 - Apr 30
Vine & Sand
Individually decorated, individually furnished, iron/ironing board
Windward Shores Ocean Resort
Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (311 reviews)
Just a 15-minute walk from The Hamptons Beaches, this Amagansett aparthotel offers clean rooms with refrigerators and microwaves. Enjoy the seasonal outdoor pool and tennis courts while exploring nearby Walking Dunes Trailhead and Hither Hills State Park.
The price is $148
$197 total
includes taxes & fees
Apr 29 - Apr 30
Windward Shores Ocean Resort
Beach nearby, white sand, sun loungers, beach umbrellas
The Roundtree, Amagansett
The Roundtree, Amagansett
4.5 star property
Amagansett North
10.0 out of 10, Exceptional, (94 reviews)
Immerse yourself in luxury at this Amagansett gem near The Hamptons Beaches. Enjoy free continental breakfast, WiFi, parking, and bike rentals for exploring nearby trails. Just a 10-minute walk from Amagansett Station and close to local attractions.
The price is $694
$833 total
includes taxes & fees
Apr 29 - Apr 30
The Roundtree, Amagansett
Cottage | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
The Reform Club
The Reform Club
2.0 star property
Amagansett North
10.0 out of 10, Exceptional, (2 reviews)
Nestled in Amagansett, this tranquil hotel offers free breakfast, WiFi and valet parking. Pamper yourself with deep-tissue massages or explore nearby attractions using complimentary bike rentals. The beach shuttle makes coastal visits effortless.
The price is $813
$1,003 total
includes taxes & fees
May 18 - May 19
The Reform Club
View from property
Journey East Hampton
Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (170 reviews)
Bask in East Hampton charm at this hotel offering complimentary breakfast and bicycles. A seasonal outdoor pool awaits after exploring nearby Atlantic Double Dunes Preserve or Amelia Cottage Museum. The coffee shop and garden create a peaceful retreat within 2 minutes of Amagansett Station.
The price is $266
$334 total
includes taxes & fees
May 10 - May 11
Journey East Hampton
Deluxe Studio | Living area | TV
East Hampton House Resort
East Hampton House Resort
3.0 star property
East Hampton North
9.0 out of 10, Wonderful, (298 reviews)
Discover seaside serenity at this East Hampton retreat with a seasonal outdoor pool and fitness center. Just a short drive from Amagansett Station, this hotel offers easy beach access plus garden views and a terrace. Rooms include convenient refrigerators and microwaves.
The price is $216
$269 total
includes taxes & fees
Apr 29 - Apr 30
East Hampton House Resort
Front of property - evening/night
Mill House Inn
Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (83 reviews)
Wake up to a complimentary cooked-to-order breakfast at this luxury B&B near The Hamptons Beaches. Adventure seekers can explore nearby hiking trails and kayaking spots, while free WiFi and parking add convenience for trips to Old Hook Mill.
The price is $375
$471 total
includes taxes & fees
Apr 29 - Apr 30
Mill House Inn
Beach nearby
The Huntting Inn
The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (105 reviews)
Escape to this historic inn featuring Italian cuisine at The Palm restaurant and relaxing garden spaces. Just minutes from Osborn-Jackson House Museum and local beaches, with free breakfast, WiFi, and parking for a hassle-free Hamptons experience.
The price is $431
$503 total
includes taxes & fees
May 11 - May 12
The Huntting Inn
2 restaurants, American cuisine
The 1770 House Restaurant & Inn
The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (164 reviews)
This charming inn offers American cuisine at its renowned restaurant, with a cozy bar/lounge for evening relaxation. Free WiFi and parking enhance your stay while Guild Hall and Mulford Farm await nearby exploration.
The price is $374
$511 total
includes taxes & fees
May 3 - May 4
The 1770 House Restaurant & Inn
Property entrance
The Maidstone
The Maidstone
4.0 star property
East Hampton
8.0 out of 10, Very Good, (157 reviews)
Escape to The Hamptons in style at this East Hampton boutique hotel. Borrow complimentary bikes to explore or catch the beach shuttle to nearby shores. After sandy adventures, unwind in the garden or sip drinks at the on-site bar.
The price is $348
$397 total
includes taxes & fees
Apr 29 - Apr 30
The Maidstone
2 restaurants, breakfast, lunch, dinner served; Mediterranean cuisine
EHP Resort & Marina
EHP Resort & Marina
3.5 star property
East Hampton
7.4 out of 10, Good, (9 reviews)
This waterfront hotel in East Hampton offers a marina, seasonal outdoor pool with bar, and two restaurants including Sí Sí serving Mediterranean cuisine. Near Three Mile Harbor with convenient access to Amagansett Station, rooms include refrigerators and microwaves.
The price is $316
$397 total
includes taxes & fees
Apr 29 - Apr 30
EHP Resort & Marina
Exterior
Wainscott Woods Retreat
Wainscott Woods Retreat
2.5 star property
Wainscott
7.0 out of 10, Good, (9 reviews)
This tranquil retreat sits adjacent to a golf course and near Wolffer Estates Vineyard. Enjoy complimentary WiFi and parking while relaxing in the seasonal outdoor pool. A garden and terrace create perfect spots for unwinding after exploring SagPond Vineyards.
The price is $650
$743 total
includes taxes & fees
Apr 29 - Apr 30
Wainscott Woods Retreat
Property entrance
The Sagaponack
The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (250 reviews)
Escape to this charming Wainscott B&B offering a refreshing seasonal outdoor pool and complimentary WiFi and parking. Just a 5-minute drive from stunning Hamptons Beaches and Wolffer Estates Vineyard, with attentive staff praised by past guests.
The price is $229
$297 total
includes taxes & fees
May 4 - May 5
The Sagaponack
Exterior
A Room At The Beach
A Room At The Beach
3.0 star property
Bridgehampton
9.2 out of 10, Wonderful, (92 reviews)
Escape to this tranquil Hamptons motel where the outdoor pool invites endless relaxation. Borrow free bicycles to explore nearby beaches or walk to Bridgehampton Station. The Hamptons Beaches and Natural History Museum are just minutes from your 24-hour attended haven.
The price is $329
$376 total
includes taxes & fees
Apr 29 - Apr 30
A Room At The Beach
Outdoor pool
Topping Rose House
Topping Rose House
4.5 star property
Bridgehampton
9.0 out of 10, Wonderful, (149 reviews)
Indulge in hot stone massages at the full-service spa or savor meals at Topping Rose restaurant. Just a 13-minute walk from Bridgehampton Station with an outdoor pool, fitness center, and bar for a complete luxury escape.
The price is $315
$363 total
includes taxes & fees
Apr 29 - Apr 30
Topping Rose House
Beach nearby
The Niantic Inn
The Niantic Inn
2.5 star property
Niantic
9.2 out of 10, Wonderful, (155 reviews)
Experience seaside charm at this Connecticut hotel, steps from the train station. Explore nearby Tumbleweeds and Children's Museum, then return to comfortable accommodations. Free WiFi and parking make your stay convenient while daily housekeeping ensures comfort.
The price is $158
$182 total
includes taxes & fees
Apr 29 - Apr 30
The Niantic Inn
Bar (on property)
Bridgehampton Inn
Bridgehampton Inn
3.5 star property
Bridgehampton
9.4 out of 10, Exceptional, (222 reviews)
Immerse in Bridgehampton charm at this inviting inn with restaurant and bar. Just 8 minutes from the train station and close to Hampton Classic Horse Show Grounds. Enjoy complimentary WiFi and parking while friendly staff ensure a memorable Hamptons getaway.
The price is $299
$342 total
includes taxes & fees
Apr 29 - Apr 30
Bridgehampton Inn
Building design
Sag Harbor Inn
Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (605 reviews)
Wake up to complimentary breakfast at this waterfront hotel, just moments from Sag Harbor Whaling Museum. The outdoor pool offers refreshing relaxation after exploring nearby attractions. Free WiFi and parking enhance the value, while the attentive staff ensures a memorable stay.
The price is $225
$257 total
includes taxes & fees
Apr 29 - Apr 30
Sag Harbor Inn
Property grounds
Southampton Village Motel
Southampton Village Motel
2.5 star property
Southampton
9.2 out of 10, Wonderful, (54 reviews)
The price is $454
$518 total
includes taxes & fees
May 17 - May 18
Southampton Village Motel
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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When is the best time to visit Southold?

Our prices for hotels in Southold are cheapest in November
Price trends for hotels in Southold
Pricing is based on two traveler single night rates
View properties in April
Currently viewing crowd sizes and weather for April.
Typical weather for Southold
April
High 10°C / low 7°C. Sunny most days.
View properties in April
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April, no crowd data, average high temperature 10 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
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May, no crowd data, average high temperature 15 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
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June, no crowd data, average high temperature 20 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
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July, no crowd data, average high temperature 24 degrees Celsius, average low temperature 21 degrees Celsius. Sunny most days.
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August, no crowd data, average high temperature 25 degrees Celsius, average low temperature 22 degrees Celsius. Sunny most days.
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September, no crowd data, average high temperature 22 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
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October, no crowd data, average high temperature 17 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
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November, no crowd data, average high temperature 12 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
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December, no crowd data, average high temperature 8 degrees Celsius, average low temperature 4 degrees Celsius. Cloudy most days.
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January, no crowd data, average high temperature 4 degrees Celsius, average low temperature 0 degrees Celsius. Partly sunny.
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February, no crowd data, average high temperature 4 degrees Celsius, average low temperature 0 degrees Celsius. Cloudy most days.
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March, no crowd data, average high temperature 6 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
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Monthly weather averages (˚C)

Top landmarks in Southold

Sparkling Pointe

4.4/5 (11 reviews)
Travelers might want a tour of Sparkling Pointe, just one of the places to visit, and located 1 mi (1.6 km) from central Southold.
See properties

Learn more about Southold

Southold is well-known for its attractions such as Sparkling Pointe and Mattebella Vineyards. The city has something for everyone including sights like Croteaux Vineyards and Horton Lane Beach within a sunny setting.

See all hotels in Southold
Photo by Benny Goh
Open Photo by Benny Goh

Check out reviews of Southold hotels guests love

Madison Beach Hotel

Madison Beach Hotel

10/10 Excellent
"Excellent hotel, high quality in every way, beautiful setting, very quiet relaxing and peaceful Sunday night stay off-season."
Melanie 1-night trip
Posted 8 hours ago
Madison Beach Hotel

Frequently asked questions

What accommodations do travelers recommend in Southold?
Guests like The Shoals Suites and Slips, Vine & Sand and Sound View Greenport.
Can I book refundable accommodations in Southold?
If you want the flexibility to change your travel plans to Southold, most properties offer refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Southold if I want a vacation home instead of a traditional hotel?
If you want to find a good alternative to a hotel, browse our selection of 117 vacation homes. You can also consider one of the 5 apartments or 13 cottages.
What will the weather in Southold be like during my vacation?
The warmest months in Southold are usually August and July with an average temp of 70°F. January and February are the chilliest months when the average temp is 38°F. The rainiest months are October and December.
Why should I book my Southold accommodation with Hotels.com?
There are plenty of reasons to book your Southold travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.