Hotels in Southold

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Check prices for these dates

Tonight
Sep 23 - Sep 24
Tomorrow
Sep 24 - Sep 25
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Where to stay in Southold?

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.
A modern living room with a blue sofa, light blue armchairs, a dining table, and a kitchen in the background.
A light blue bus with "THE SHOALS" written on the front, parked in a driveway with a house and garden in the background.
A modern hotel room with a bed, a sofa, a coffee table, and a view of the city.

1. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
$229
$286 total
includes taxes & fees
Oct 1 - Oct 2
The Shoals Suites and Slips
A spacious room with wicker furniture, large windows, and a view of the sea.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.
A coastal building with large windows, a deck, and a view of the sea at sunset.
A coastal building with a deck extending over the water, featuring large windows and a dining area.

2. Sound View Greenport

Sound View Greenport
Greenport
$269
$336 total
includes taxes & fees
Oct 18 - Oct 19
Sound View Greenport
A two-story house with a balcony, outdoor seating area, and a variety of plants.
A restaurant with a signboard listing its hours of operation.
A bathroom with a bathtub, green tiled walls, and windows with white blinds.
A bar area with stools, a shelf with glasses, and decorative plants.

3. Zey Hotel

Zey Hotel
Greenport
$191
$218 total
includes taxes & fees
Sep 27 - Sep 28
Zey Hotel
A seaside dining area with tables, chairs, and umbrellas, overlooking a body of water.
A grassy area with trees and a view of a body of water.
A beach with sun loungers and umbrellas, a sandy path, and a view of the water.

4. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
$325
$371 total
includes taxes & fees
Oct 12 - Oct 13
Silver Sands Motel & Beach Bungalows
An outdoor patio area with string lights, tables, chairs, and a fire pit.
A modern hotel room with a large bed, a sofa, a chair, a small table, and a mirror.
A large, white building with multiple windows and a prominent tree in the foreground.
A staircase with wooden balusters and a white wall.

5. The Chequit

The Chequit
The Heights
$207
$237 total
includes taxes & fees
Oct 4 - Oct 5
The Chequit
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.
A neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.
A large building with multiple floors, surrounded by a residential area with houses and a body of water.

6. The Harbor Front Inn

The Harbor Front Inn
Greenport
$279
$347 total
includes taxes & fees
Oct 15 - Oct 16
The Harbor Front Inn

7. Shelter Island House

Shelter Island House
Shelter Island Heights
$201
$230 total
includes taxes & fees
Oct 4 - Oct 5
Shelter Island House

8. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
$337
$496 total
includes taxes & fees
Sep 27 - Sep 28
Cliffside Resort Condominiums
A serene landscape with a calm body of water reflecting trees with autumn foliage.
A serene lakeside view with two Adirondack chairs facing a calm lake, surrounded by trees and a clear sky.
A sign for 'House on Chase Creek' with a duck illustration.
A conservatory with a dining table set for four, surrounded by wooden chairs, with a view of trees and a lawn.

9. House on Chase Creek

House on Chase Creek
The Heights
$215
$246 total
includes taxes & fees
Oct 5 - Oct 6
House on Chase Creek
A modern house with a deck, outdoor seating, and a fire pit.
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.
A modern living room with a sofa, a dining table, and a kitchen area in the background.
A tented accommodation with a bed, television, and a small table with a chair.

10. North Fork Resort

North Fork Resort
Greenport
$300
$342 total
includes taxes & fees
Oct 18 - Oct 19
North Fork Resort
A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.
A rooftop deck with outdoor seating, fire pits, and a view of a body of water.
A modern bar area with black bar stools, a counter with a variety of bottles, and hanging green plants in wire baskets.
A modern reception area with a staircase, a framed artwork, and a reception desk with "THE MENHADEN" signage.

11. The Menhaden

The Menhaden
Greenport
$334
$421 total
includes taxes & fees
Sep 29 - Sep 30
The Menhaden
A poolside area with lounge chairs and yellow umbrellas.
A cozy interior with a wooden bench, a sofa, and a bar area.
A cozy interior with a bar area, seating, and a fireplace.
A bedroom with a large bed, bedside tables, a window with curtains, and wooden shelving with various items.

12. Oyster Estate

Oyster Estate
Greenport
$316
$398 total
includes taxes & fees
Oct 8 - Oct 9
Oyster Estate
A parking lot with a building in the background.
A hotel room with a large bed, two bedside tables, a desk with chairs, a TV, and a small table with flowers.
A motel with a large parking lot and multiple rooms.
A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.

13. Clinton Motel

Clinton Motel
Clinton
$79
$91 total
includes taxes & fees
Sep 24 - Sep 25
Clinton Motel
An outdoor seating area with Adirondack chairs and a table, surrounded by American flags and flowers, with a view of houses and a body of water in the background.
A bedroom with a bed, a desk, a chair, a window with a view of trees and a body of water.
A window with a view of a building and trees, a small table with a lamp, and a curtain partially covering the window.
Two Adirondack chairs facing a beach with a clear view of the sea and a distant island.

14. Ocean View Terrace Inn

Ocean View Terrace Inn
Hampton Bays
$121
$195 total
includes taxes & fees
Sep 24 - Sep 25
Ocean View Terrace Inn
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.
A modern lounge area with a curved sofa, round coffee tables, and a large potted plant.
An outdoor dining area with tables and chairs, string lights, and hanging lanterns.
A reception desk with a white backdrop, surrounded by various plants and a modern pendant light.

15. American Beech Hotel

American Beech Hotel
Greenport
$229
$302 total
includes taxes & fees
Oct 1 - Oct 2
American Beech Hotel
A glass-top table with a vase of flowers, surrounded by white-covered chairs, in a bright indoor setting with plants and a fireplace in the background.
A room with a wicker sofa, a small table with a potted plant, and a bed with a wooden ladder.
A beach scene with a sunset, calm sea, and a few people fishing.
A house with a covered porch, a garden with various plants and flowers, and a 'OPEN' sign on the window.

16. Hamlet Inn

Hamlet Inn
Southampton
$144
$186 total
includes taxes & fees
Sep 27 - Sep 28
Hamlet Inn
A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.
A white closet with shelves, a robe hanging on a wooden hanger, and a pair of black straps on a rack.
A breakfast bar with cereal, coffee, and fresh milk.
A bedroom with a bed, a door, and a framed picture on the wall.

17. Shorewood Inn

Shorewood Inn
Riverhead
$97
$111 total
includes taxes & fees
Sep 24 - Sep 25
Shorewood Inn
A sign for Pier Blue Guesthouse with a logo and name.
A guesthouse named Pier Blue with a sign, a parking lot, and a building with a red awning.
A train traveling along a river with autumn foliage in the background.
Two blue Adirondack chairs and a small white table in a grassy area surrounded by trees.

18. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
$91
$104 total
includes taxes & fees
Sep 30 - Oct 1
Pier Blue Inn Old Saybrook - Essex
A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.
A hotel lobby with a reception desk, two sofas, a coffee table, and a carpeted floor.
A hotel room with a large bed, a bathroom with a bathtub, a TV on a wooden cabinet, and a chair.
A dining area with tables and chairs, a clock on the wall, and a counter with food items.

19. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
$101
$116 total
includes taxes & fees
Oct 14 - Oct 15
Quality Inn Old Saybrook - Westbrook
A bedroom with a bed, bedside tables, a lamp, a window, and a door.
A beach with a wooden walkway along the shore, calm water, and a sunset sky.
A backyard with a large chessboard, outdoor furniture, and a house.
A large, light blue two-story house with a steep roof, surrounded by greenery and a gravel driveway.

20. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
West Neck Guesthouse
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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 September
Typical weather for Southold
September
High 22°C / low 19°C. Sunny most days.
View properties in September
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Monthly weather averages (˚C)

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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Croteaux Vineyards

10.0/10 (12 reviews)
Travelers might want a tour of Croteaux Vineyards, just one of the places to visit, and located 1.5 mi (2.4 km) from central Southold. Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy your tour, head to Mattebella Vineyards or Corey Creek Winery, both within a short walk.
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Sannino's Bella Vita Vineyard

9.6/10 (4 reviews)
Travelers might want a tour of Sannino's Bella Vita Vineyard, just one of the places to visit, and located 2.2 mi (3.5 km) from central Southold. If you enjoy your tour, head to Osprey's Dominion, just a short walk away.
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Horton Point Park

9.4/10 (3 reviews)
Horton Point Park is 1.7 mi (2.8 km) from central Southold, why not stop by during your stay. Want to stretch your legs some more? Head to Goldsmith's Inlet Park, located nearby.
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Osprey's Dominion

9.6/10 (5 reviews)
Travelers might want a tour of Osprey's Dominion, just one of the places to visit, and located 1.9 mi (3 km) from central Southold. Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy your tour, head to Sannino's Bella Vita Vineyard or Corey Creek Winery, both within a short walk.
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Mattebella Vineyards

8.0/10 (4 reviews)
Travelers might want a tour of Mattebella Vineyards, just one of the places to visit, and located 1.4 mi (2.3 km) from central Southold. Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy your tour, head to Croteaux Vineyards or Corey Creek Winery, both within a short walk.
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Horton Lane Beach

9.0/10 (4 reviews)
If you can't wait to get to the beach, you might enjoy a trip to Horton Lane Beach located 1.6 mi (2.6 km) from central Southold. If you want to continue walking by the waves, head to McCabe's Beach located nearby.
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Corey Creek Winery

9.6/10 (5 reviews)
Travelers might want a tour of Corey Creek Winery, just one of the places to visit, and located 1.7 mi (2.7 km) from central Southold. Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy your tour, head to Croteaux Vineyards or Mattebella Vineyards, both within a short walk.
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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 Custer Institute and Observatory 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

Check out reviews of Southold hotels guests love

Zey Hotel

Zey Hotel

10/10 Excellent
"Lovely hotel, great location and lovely courtyard!"
Martina 1-night trip
Posted less than an hour ago
Zey Hotel
Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good
"The staff at the Bistro Bar weren't very good. Also the drinks sub par. I ordered a gin and tonic, they served me soda water twice."
Linda 3-night trip
Posted 4 hours ago
Water's Edge Resort & Spa
The Hampton Maid

The Hampton Maid

10/10 Excellent
"It’s a beautiful property, we had breakfast at the restaurant on the property and it was great! Will come back."
Simranjit 1-night trip
Posted 7 hours ago
The Hampton Maid
Sag Harbor Inn

Sag Harbor Inn

10/10 Excellent
"Great place to stay in Sag Harbor. Walking distance to everything and also quiet and peaceful. Helpful staff and nice that there was 24/7 coffee and tea in lobby."
Stephen 2-night trip
Posted 7 hours ago
Sag Harbor Inn
Sound View Greenport

Sound View Greenport

10/10 Excellent
"The sunsets are incredible, different each time and it’s like the whole property pauses for that moment, fantastic views."
KRIS E 1-night trip
Posted 1 day ago
Sound View Greenport
The Shoals Suites and Slips

The Shoals Suites and Slips

10/10 Excellent
"This place is awesome! It is very well appointed and very comfortable beds. It's a beautiful space with lots of outdoor space and lovely views of the small marina next door. We were in town for just one night, wish we could have stayed longer. I'd go back in a heartbeat!"
Susan 1-night trip
Posted 1 day ago
The Shoals Suites and Slips
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Beautiful and clean room and property with a gorgeous marina view. Friendly and helpful staff. I thoroughly enjoyed my stay, and intend to return."
Joseph 1-night trip
Posted 1 day ago
Saybrook Point Resort & Marina
Budget Host East End

Budget Host East End

8/10 Good
"Staff"
Harvey 2-night trip
Posted 2 days ago
Budget Host East End
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"Great place."
Christine 3-night trip
Posted 3 days ago
Hilton Garden Inn Riverhead

Frequently asked questions

What accommodations do travelers recommend in Southold?
Guests like The Shoals Suites and Slips, Sound View Greenport and Zey Hotel.
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 12 cottages for your trip.
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.

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