Photo by Benny Goh

Hotels in Southold

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This weekend
Jun 5 - Jun 7
Next weekend
Jun 12 - Jun 14

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, (275 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
Jun 2 - Jun 3
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.
Vine & Sand
Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (253 reviews)
The price is $249
$328 total
includes taxes & fees
Jun 21 - Jun 22
Cliffside Resort Condominiums
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (19 reviews)
The price is $293
$334 total
includes taxes & fees
Jun 2 - Jun 3
North Fork Resort
Terrace/patio

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (85 reviews)
Perched on the bay, this coastal retreat offers a private beach, outdoor pool, and spa with hydrotherapy treatments. The seasonal restaurant serves local cuisine while proximity to Crescent Beach and Sunset Beach enhances your island getaway.
The price is $465
$584 total
includes taxes & fees
Jun 7 - Jun 8
The Pridwin Hotel
Front of property - evening/night

Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very Good, (58 reviews)
Tucked away in Shelter Island Heights, this golf-adjacent hotel offers a seasonal outdoor pool and rejuvenating massage services. Enjoy cocktails at the poolside bar, grab bites at the restaurant or deli, then explore nearby Sunset Beach and Shelter Island Country Club.
The price is $201
$230 total
includes taxes & fees
Jun 3 - Jun 4
Shelter Island House
Exterior

Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (309 reviews)
Stylish rooms in this boutique hotel offer a peaceful retreat after exploring the harbor. Unwind with a drink at the bar, grab a bite at the coffee shop, or bike to nearby Greenport Harbor Brewing Company and Farmers' Market.
The price is $180
$206 total
includes taxes & fees
Jun 2 - Jun 3
Zey Hotel
Beach bar

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (153 reviews)
The price is $450
$514 total
includes taxes & fees
Jun 2 - Jun 3
Silver Sands Motel & Beach Bungalows
Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, free WiFi, bed sheets

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.0 out of 10, Very Good, (37 reviews)
Wake up to a fresh continental breakfast at this coastal B&B offering a seasonal outdoor pool and complimentary bicycles for island exploration. Located near Shelter Island Country Club and Sunset Beach, guests enjoy free WiFi and parking in this tranquil garden setting.
The price is $219
$250 total
includes taxes & fees
Jun 7 - Jun 8
West Neck Guesthouse
Resort view

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (651 reviews)
Perched oceanfront in Greenport, this hotel offers a seasonal outdoor pool with poolside bar. Just a short drive from the Railroad Museum and The Old Field Vineyards, enjoy American cuisine at The Halyard restaurant and unwind at 2 welcoming bars.
The price is $375
$514 total
includes taxes & fees
Jun 2 - Jun 3
Sound View Greenport
View from property

House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (82 reviews)
Overlooking Chase Creek, this inviting guesthouse sits adjacent to a golf course in tranquil Shelter Island Heights. Free WiFi and parking enhance your stay while the garden and terrace offer peaceful spots to unwind near Shelter Island Country Club.
The price is $276
$315 total
includes taxes & fees
Jun 2 - Jun 3
House on Chase Creek
Lobby lounge

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (607 reviews)
Overlooking Greenport Harbor, this boutique inn combines coastal charm with modern comforts. Just a 3-minute walk from the train station, guests enjoy the seasonal outdoor pool, 24-hour fitness center, and complimentary breakfast while exploring nearby attractions.
The price is $321
$418 total
includes taxes & fees
Jun 9 - Jun 10
The Harbor Front Inn
Property entrance

The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (183 reviews)
Escape to this stylish Greenport retreat offering free breakfast and WiFi. Relax at the rooftop terrace or grab a drink from the bar before exploring local attractions on complimentary bikes. Only a 3-minute walk from Greenport Station, near Camera Obscura.
The price is $424
$525 total
includes taxes & fees
Jun 2 - Jun 3
The Menhaden
Terrace/patio

American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (200 reviews)
Explore Greenport from this stylish inn with its welcoming bar and restaurant. Grab the complimentary bikes to visit nearby Greenport Harbor Brewing Company. The attentive staff and daily housekeeping ensure a carefree stay, just an 8-minute walk from the train station.
The price is $259
$336 total
includes taxes & fees
Jun 3 - Jun 4
American Beech Hotel
Outdoor dining

The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (37 reviews)
Wake to island tranquility at this Shelter Island Heights hotel with premium bedding. Near Shelter Island Country Club and Sunset Beach, this refined retreat offers free WiFi and parking. Convenient to Greenport Station for day trips.
The price is $634
$724 total
includes taxes & fees
Jun 2 - Jun 3
The Chequit
Building design

Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (621 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 $315
$360 total
includes taxes & fees
Jun 2 - Jun 3
Sag Harbor 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 $825
$1,037 total
includes taxes & fees
Jun 7 - Jun 8
Faraway Sag Harbor
Exterior

Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.6 out of 10, Excellent, (758 reviews)
Steps from Riverhead's renowned vineyards, this welcoming motel offers free WiFi and complimentary parking. The 24-hour front desk ensures convenience while clean, comfortable rooms provide a relaxing base to explore nearby Westhampton beaches.
The price is $98
$112 total
includes taxes & fees
Jun 2 - Jun 3
Shorewood Inn
Desk, free WiFi, bed sheets

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
Southampton
8.6 out of 10, Excellent, (210 reviews)
Dive into vacation mode at this Southampton retreat, just a 10-minute drive from Cooper's Beach. After exploring nearby attractions, cool off in the outdoor pool. Complimentary WiFi and self parking enhance your coastal escape.
The price is $284
$339 total
includes taxes & fees
Jun 30 - Jul 1
Southampton Long Island Hotel
Honeymoon Room, Jetted Tub | Egyptian cotton sheets, premium bedding, desk, laptop workspace

The Atlantic Hotel

The Atlantic Hotel
2.5 star property
Southampton
7.2 out of 10, Good, (1,002 reviews)
Overlooking the ocean in Southampton, this hotel offers refreshing swims in an outdoor pool and matches on tennis courts. Guests praise the helpful staff while enjoying free WiFi and parking, with Sebonack Golf Course nearby.
The price is $199
$252 total
includes taxes & fees
Jun 2 - Jun 3
The Atlantic 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.
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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 June
Currently viewing crowd sizes and weather for June.
Typical weather for Southold
June
High 20°C / low 17°C. Sunny most days.
View properties in June
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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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May, no crowd data, average high temperature 15 degrees Celsius, average low temperature 12 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.
See properties

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 Corey Creek Winery and Horton Point Park 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

Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

8/10 Good
"Everything was good 👍"
Kenneth 3-night trip
Posted 2 hours ago
Hilton Garden Inn Riverhead

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.