Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Town of Southold Town on Hotels.com. These Town of Southold Town hotels consistently deliver on quality, location and traveler experience. Last updated on .
Town of Southold Town Hotels
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Top hotels in Greenport

Sound View Greenport

Zey Hotel
9.2/10 Wonderful! (417 reviews)

The Harbor Front Inn
9/10 Wonderful! (661 reviews)

Silver Sands Motel & Beach Bungalows
10/10 Exceptional! (172 reviews)

The Menhaden

American Beech Hotel

Oyster Estate
9.2/10 Wonderful! (291 reviews)

Harbor Knoll Bed & Breakfast
Pipes Cove
‐0.61 km from city center
Stirling House Bed & Breakfast
9.8/10 Exceptional! (28 reviews)

Hotel Moraine

Fordham House

Victorian Seasons Stirling
Top hotels in Southold

The Shoals Suites and Slips
9.4/10 Exceptional! (344 reviews)

Vine & Sand
9.8/10 Exceptional! (20 reviews)

White Blossom House Inn
10/10 Exceptional! (6 reviews)
Top hotels in Cutchogue

The Farmhouse Bed and Breakfast
10/10 Exceptional! (16 reviews)

North Fork Guest House
Top cities in Town of Southold Town
Greenport
Greenport is known for its beaches, and offers lots of things to see including Greenport Carousel and East End Seaport Maritime Museum.
Southold
Southold has lots of attractions such as Sparkling Pointe and Croteaux Vineyards.
Mattituck
Mattituck has lots of attractions such as Macari Vineyards and Harbes Family Farm.
Cutchogue
Cutchogue has lots of attractions such as Peconic Bay Winery and Bedell Cellars.
Orient
Orient has lots of attractions such as Orient Beach State Park and Orient Point County Park.
East Marion
East Marion has lots of attractions such as Orient Beach State Park and Island's End Golf and Country Club.
Top landmarks in Town of Southold Town

Orient Point County Park
10.0/10 (1 review)
Orient Point County Park is 0.8 mi (1.2 km) from central Orient Point, why not stop by during your stay. If you like Orient Point County Park, you'll love Mashomack Preserve and Cedar Point County Park, both just a short drive away.
Photo by Joe Vickiana
Orient Beach State Park
8.6/10 (33 reviews)
Orient Beach State Park is 2 mi (3.3 km) from central Orient, why not stop by during your stay.
Photo by Adriana T
Bedell Cellars
8.6/10 (4 reviews)
Travelers might want a tour of Bedell Cellars, just one of the places to visit, and located 1.5 mi (2.5 km) from central Cutchogue.
Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy your tour, head to Pindar Vineyards or Lenz Winery, both within a short walk.
Raphael Winery
Travelers might want a tour of Raphael Winery, just one of the places to visit, and located 0.9 mi (1.5 km) from central Peconic.
If you enjoy your tour, head to Pindar Vineyards or Lenz Winery, both within a short walk.
67 Steps Beach
9.6/10 (26 reviews)
If you can't wait to get to the beach, you might enjoy a trip to 67 Steps Beach located 1.3 mi (2.1 km) from central Greenport. Enjoy the sunset by the shore at Sunset Beach, Crescent Beach, and Norman E. Klipp Marine Park.
Harbes Family Farm
10.0/10 (2 reviews)
If you like the hustle and bustle of a market, you might want to head out to Harbes Family Farm when visiting Mattituck. Why not take a stroll along the beaches and watch the sunset while you're here?
Kontokosta Winery
9.2/10 (48 reviews)
Travelers might want a tour of Kontokosta Winery, just one of the places to visit, and located 1.9 mi (3.1 km) from central Greenport West.
Why not take a stroll along the beaches and watch the sunset while you're here?
Greenport Carousel
9.4/10 (50 reviews)
If you're planning a bit of sightseeing during your trip, head to Greenport Carousel— just one of the monuments in central Greenport. If you have fun at Greenport Carousel, you'll love East End Seaport Maritime Museum and Railroad Museum of Long Island, both a short walk away.
Check out the Town of Southold Town hotels guests love right now
Zey Hotel
10/10 Excellent
"Had a great stay here. James was very welcoming and a great host. The town is great with nice shops and restaurants."
Silver Sands Motel & Beach Bungalows
10/10 Excellent
"Property was well maintained and the rooms were so thought out from there coffee pot to the slippers and bathrobes!!! Staff was very courteous. Nookies was a great place to have breakfast and there freshly made donuts are so tasty and delicious. I highly recommend staying there for a the beautiful views and the quiet rooms. Well go again"
The Shoals Suites and Slips
10/10 Excellent
"The staff were all great, the food from food truck was delicious, check in was quick!"
The Harbor Front Inn
10/10 Excellent
"The hotel was just what we expected, cozy and comfortable and nestled right into central Greenport. Close to everything, dinner spots just steps away. Will definitely return."
Oyster Estate
10/10 Excellent
"Newly renovated. Place looks great."
American Beech Hotel
10/10 Excellent
"Fun picnic breakfast left at the door at 9am"
Find out more about Town of Southold Town
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