Photo by Benny Goh

Hotels in Southold

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Check prices for these dates

This weekend
May 22 - May 24
Next weekend
May 29 - May 31

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, (269 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 $242
$302 total
includes taxes & fees
May 25 - May 26
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 $456
$521 total
includes taxes & fees
May 27 - May 28
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, (313 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 $216
$274 total
includes taxes & fees
May 25 - May 26
Windward Shores Ocean Resort
Cozy Pad 2BR Beachside Home | TennisPoolFreePKG Unit 721 | Terrace/patio

Ocean Colony Beach and Tennis Club

Ocean Colony Beach and Tennis Club
2.0 star property
Napeague
2.0 out of 10, (1 review)
The price is $667
$1,123 total
includes taxes & fees
May 22 - May 23
Ocean Colony Beach and Tennis Club
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 $994
$1,192 total
includes taxes & fees
Jun 1 - Jun 2
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 $731
$902 total
includes taxes & fees
May 31 - Jun 1
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, (175 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 $332
$417 total
includes taxes & fees
May 27 - May 28
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, (299 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 $239
$300 total
includes taxes & fees
Jun 1 - Jun 2
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, (84 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 $625
$785 total
includes taxes & fees
May 29 - May 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 $602
$698 total
includes taxes & fees
Jun 7 - Jun 8
The Huntting Inn
Outdoor dining

The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (165 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 $661
$904 total
includes taxes & fees
May 26 - May 27
The 1770 House Restaurant & Inn
Beach nearby, sun loungers, beach umbrellas, beach towels

The Hedges Inn

The Hedges Inn
3.5 star property
East Hampton
9.6 out of 10, Exceptional, (73 reviews)
The price is $799
$962 total
includes taxes & fees
Jun 11 - Jun 12
The Hedges 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 $464
$530 total
includes taxes & fees
May 31 - Jun 1
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 $460
$578 total
includes taxes & fees
May 25 - May 26
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 $545
$623 total
includes taxes & fees
May 24 - May 25
Wainscott Woods Retreat
Property entrance

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (257 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 $239
$308 total
includes taxes & fees
May 25 - May 26
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 $569
$650 total
includes taxes & fees
May 25 - May 26
A Room At The Beach
Outdoor pool

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.0 out of 10, Wonderful, (151 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 $695
$798 total
includes taxes & fees
May 27 - May 28
Topping Rose House
Beach nearby

The Niantic Inn

The Niantic Inn
2.5 star property
Niantic
9.2 out of 10, Wonderful, (160 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 $190
$218 total
includes taxes & fees
May 25 - May 26
The Niantic Inn
Exterior

Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (292 reviews)
Immerse in coastal charm at this Sag Harbor retreat where massages await after beach days. The seasonal outdoor pool offers refreshment while the fitness center keeps routines intact. Friendly staff ensure a memorable stay near historical museums.
The price is $750
$943 total
includes taxes & fees
Jun 10 - Jun 11
Faraway Sag Harbor
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 May
Currently viewing crowd sizes and weather for May.
Typical weather for Southold
May
High 15°C / low 12°C. Sunny most days.
View properties in May
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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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April, no crowd data, average high temperature 10 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
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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.
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Learn more about Southold

Southold is well-known for its attractions such as Croteaux Vineyards and Horton Lane Beach. The city has something for everyone including sights like Osprey's Dominion and Sannino's Bella Vita Vineyard 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

Spark by Hilton Guilford

Spark by Hilton Guilford

10/10 Excellent
"From start to finish the experience was stellar. Smooth check in. Super courteous staff and exceptional facilities "
Frank 1-night trip
Posted 18 hours ago
Spark by Hilton Guilford

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 118 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.