Hotels in Southold

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Jul 24 - Jul 26
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Jul 31 - Aug 2

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, (297 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 $413
$497 total
includes taxes & fees
Jul 21 - Jul 22
The Shoals Suites and Slips
Resort view

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (667 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 $339
$473 total
includes taxes & fees
Aug 12 - Aug 13
Sound View Greenport
Exterior

Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (354 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 $270
$308 total
includes taxes & fees
Jul 29 - Jul 30
Zey Hotel
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, (1,003 reviews)
Tucked beside Old Saybrook Station, this peaceful inn offers comfortable beds and free parking. Explore nearby Chalker Beach or hike local trails before relaxing in clean rooms. Himalaya Café and The Teakettle Cafe are just steps away for tasty meals.
The price is $92
$105 total
includes taxes & fees
Jul 20 - Jul 21
Pier Blue Inn Old Saybrook - Essex
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, (60 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 $316
$361 total
includes taxes & fees
Jul 30 - Jul 31
Shelter Island House
Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (272 reviews)
The price is $355
$449 total
includes taxes & fees
Jul 23 - Jul 24
Cliffside Resort Condominiums
Property grounds

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (324 reviews)
Wake up to seaside charm at this Clinton motel where the ocean beckons nearby. Take a refreshing dip in the seasonal outdoor pool after exploring Clinton Plaza or the historic Adam Stanton House. Free WiFi and parking add value, with Clinton Station just a 19-minute walk away.
The price is $89
$102 total
includes taxes & fees
Jul 20 - Jul 21
Clinton Motel
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (33 reviews)
The price is $409
$467 total
includes taxes & fees
Jul 20 - Jul 21
North Fork Resort
Terrace/patio

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (94 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 $646
$812 total
includes taxes & fees
Jul 27 - Jul 28
The Pridwin Hotel
Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, WiFi (free), bed sheets

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very Good, (42 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 $314
$358 total
includes taxes & fees
Jul 26 - Jul 27
West Neck Guesthouse
Outdoor dining

The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (40 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 $425
$486 total
includes taxes & fees
Jul 20 - Jul 21
The Chequit
Terrace/patio

American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (202 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 $349
$439 total
includes taxes & fees
Jul 20 - Jul 21
American Beech Hotel
Exterior

Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.6 out of 10, Excellent, (780 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 $181
$207 total
includes taxes & fees
Jul 20 - Jul 21
Shorewood Inn
Beach bar

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (159 reviews)
The price is $775
$885 total
includes taxes & fees
Jul 22 - Jul 23
Silver Sands Motel & Beach Bungalows
Exterior

Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
2.5 star property
Clinton
6.4 out of 10, (245 reviews)
The price is $79
$91 total
includes taxes & fees
Jul 20 - Jul 21
Lamplighter Motel - Clinton, Connecticut
Property entrance

The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (185 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 $510
$622 total
includes taxes & fees
Jul 22 - Jul 23
The Menhaden
Frette Italian sheets, premium bedding, down comforters, pillowtop beds

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (630 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 $413
$524 total
includes taxes & fees
Aug 10 - Aug 11
The Harbor Front Inn
Deluxe Double Room, 1 King Bed, City View | In-room safe, desk, laptop workspace, WiFi (free)

Hampton Bays Hotel on Main

Hampton Bays Hotel on Main
2.0 star property
Hampton Bays
7.4 out of 10, Good, (93 reviews)
Just a 5-minute drive from The Hamptons Beaches, this hotel offers 2 bars/lounges and free WiFi. Only a 3-minute walk from Hampton Bays Station and close to Good Ground Park and Regal UA Hampton Bays for local entertainment.
The price is $150
$172 total
includes taxes & fees
Jul 21 - Jul 22
Hampton Bays Hotel on Main
Free daily continental breakfast

Spark by Hilton Guilford

Spark by Hilton Guilford
2.5 star property
Guilford
9.0 out of 10, Wonderful, (161 reviews)
Tranquil seaside accommodation near Hyland House Museum offers free breakfast, WiFi, and parking. Explore local hiking paths or visit Henry Whitfield State Museum, just minutes from Guilford Station. Guests love the helpful staff and clean, quiet rooms.
The price is $106
$122 total
includes taxes & fees
Jul 26 - Jul 27
Spark by Hilton Guilford
Lobby

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,002 reviews)
Relax at this peaceful hotel with an indoor pool and fitness center. Just a short drive from Old Saybrook Station, enjoy American cuisine at The Comfort Cafe and unwind at the bar. Free breakfast, WiFi, and parking add value near popular local attractions.
The price is $127
$146 total
includes taxes & fees
Aug 9 - Aug 10
Quality Inn Old Saybrook - Westbrook
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 July
Currently viewing crowd sizes and weather for July.
Typical weather for Southold
July
High 24°C / low 21°C. Sunny most days.
View properties in July
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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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June, no crowd data, average high temperature 20 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
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Monthly weather averages (ËšC)

Top landmarks in Southold

Sparkling Pointe

8.8/10 (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 Sparkling Pointe and Croteaux Vineyards. The city has something for everyone including sights like Sannino's Bella Vita Vineyard and The Old Field Vineyards within a sunny setting.

See all hotels in Southold
A pebbled beach at sunset with the sun reflecting on the water.
Photo by Benny Goh
Open Photo by Benny Goh

Check out reviews of Southold hotels guests love

The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Very nice property/staff and a great location"
David 2-night trip
Posted 1 hour ago
The Harbor Front Inn

Frequently asked questions

What accommodations do travelers recommend in Southold?
Guests like The Shoals Suites and Slips, Sound View Greenport and North Fork Resort.
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 115 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 Keyâ„¢, our rewards program, you will be able to earn and use OneKeyCashâ„¢* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.