Hotels in Southold

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Tonight
Oct 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

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 storefront with a sign reading "THE SHOALS".
A modern hotel room with a bed, a sofa, a coffee table, and a view of the city.
A light blue bus with "THE SHOALS" written on the front, parked in a driveway with a house and garden in the background.

1. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
$229
$286 total
includes taxes & fees
Nov 1 - Nov 2
The Shoals Suites and Slips
An outdoor patio area with string lights, tables, chairs, and a fire pit.
A large, white building with multiple windows and a prominent tree in the foreground.
A staircase with wooden balusters and a white wall.
A large, multi-story building with a porch and outdoor seating area, featuring multiple windows and a balcony.

2. The Chequit

The Chequit
The Heights
$149
$171 total
includes taxes & fees
Nov 1 - Nov 2
The Chequit
A spacious room with wicker furniture, large windows, and a view of the sea.
A spacious room with large windows, a wooden bench, yoga mats, and a door leading to a balcony with a view of the sea.
A coastal building with large windows, a deck, and a view of the sea at sunset.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.

3. Sound View Greenport

Sound View Greenport
Greenport
$192
$248 total
includes taxes & fees
Nov 2 - Nov 3
Sound View Greenport
A lakeside patio with outdoor seating and a view of the water.
A room with a bed, two wicker chairs with checkered cushions, a small round table with a vase of flowers, and a view of a lake through a window with a bamboo blind.
A grassy area with trees and a view of a body of water.
Outdoor spa tub

4. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
$280
$320 total
includes taxes & fees
Nov 1 - Nov 2
Silver Sands Motel & Beach Bungalows
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 person standing in front of a building with a sign that reads 'The Harbor Front Inn.'

5. The Harbor Front Inn

The Harbor Front Inn
Greenport
$179
$233 total
includes taxes & fees
Nov 1 - Nov 2
The Harbor Front Inn
A two-story house with a balcony, outdoor seating area, and a variety of plants.
A bar area with stools, a shelf with glasses, and decorative plants.
A restaurant with a signboard listing its hours of operation.
A modern bedroom with two beds, a sofa, a coffee table, and a potted plant.

6. Zey Hotel

Zey Hotel
Greenport
$191
$218 total
includes taxes & fees
Oct 12 - Oct 13
Zey Hotel
Front of property - evening/night
Bar (on property)
Property amenity
Terrace/patio

7. Shelter Island House

Shelter Island House
Shelter Island Heights
$201
$230 total
includes taxes & fees
Oct 12 - Oct 13
Shelter Island House
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 house with a porch, a sign reading "House on Chase Creek," and a tree with red leaves.
A conservatory with a dining table set for four, surrounded by wooden chairs, with a view of trees and a lawn.

8. House on Chase Creek

House on Chase Creek
The Heights
$185
$211 total
includes taxes & fees
Nov 2 - Nov 3
House on Chase Creek
Terrace/patio
Room
Living area
Beach

9. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
$211
$353 total
includes taxes & fees
Nov 1 - Nov 2
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.
A modern kitchen with a stainless steel sink, white cabinets, and a blue-tiled backsplash.
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.

10. North Fork Resort

North Fork Resort
Greenport
$266
$304 total
includes taxes & fees
Oct 8 - Oct 9
North Fork Resort
A waterfront property with a large house, multiple boats docked, and lush greenery.
A hotel lobby with a sofa, chairs, tables, and a large window.
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.

11. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
$219
$250 total
includes taxes & fees
Nov 1 - Nov 2
Sag Harbor Inn
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.
A modern outdoor seating area with a sofa, cushions, a wooden coffee table with a fire feature, and a decorative wall with geometric patterns.
A wooden wall with a wall-mounted lamp, a shelf with decorative items, and a bedside table with a pillow.
A dining area with a round table, chairs, a vase, and a painting on the wall.

12. Oyster Estate

Oyster Estate
Greenport
$259
$327 total
includes taxes & fees
Nov 1 - Nov 2
Oyster Estate
A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.
A reception desk with a vase of flowers, a sign that says "STAY awhile", and a window with blinds.
A white closet with shelves, a robe hanging on a wooden hanger, and a pair of black straps on a rack.
A bedroom with a bed, a door, and a framed picture on the wall.

13. Shorewood Inn

Shorewood Inn
Riverhead
$97
$111 total
includes taxes & fees
Oct 8 - Oct 9
Shorewood Inn
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.
A reception desk with a white backdrop, surrounded by various plants and a modern pendant light.
A modern lounge area with a curved sofa, round coffee tables, and a large potted plant.
A building with a red facade, a green tree in front, and a sign reading "OPENSPACE".

14. American Beech Hotel

American Beech Hotel
Greenport
$251
$327 total
includes taxes & fees
Oct 8 - Oct 9
American Beech Hotel
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 reception area with a staircase, a framed artwork, and a reception desk with "THE MENHADEN" signage.
A modern living room with a grey sofa, black and white patterned rug, and a coffee table.

15. The Menhaden

The Menhaden
Greenport
$346
$435 total
includes taxes & fees
Nov 5 - Nov 6
The Menhaden
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.
A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.
A modern outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.
A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.

16. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
$144
$165 total
includes taxes & fees
Oct 13 - Oct 14
The Bentley Hotel Southampton
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 house with a covered porch, a garden with various plants and flowers, and a 'OPEN' sign on the window.
A spacious living room with a white sofa, a coffee table, and a fireplace. There are large windows offering a view of the outdoors.
A beach scene with a sunset, calm sea, and a few people fishing.

17. Hamlet Inn

Hamlet Inn
Southampton
$127
$164 total
includes taxes & fees
Oct 8 - Oct 9
Hamlet Inn
A hotel room with a bed, bedside tables, a desk with chairs, a sofa, a window with curtains, and a door leading outside.
A hotel room with a bed, bedside tables, a desk with a chair, and a window with a view of greenery.
A kitchen counter with a coffee maker, thermos, fruits, and breakfast items.
A sign for 'The Atlantic Southampton' with a stylized logo and text.

18. The Atlantic Hotel

The Atlantic Hotel
Southampton
$101
$141 total
includes taxes & fees
Oct 28 - Oct 29
The Atlantic Hotel
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.
Two Adirondack chairs facing a beach with a clear view of the sea and a distant island.
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.

19. Ocean View Terrace Inn

Ocean View Terrace Inn
Hampton Bays
$132
$209 total
includes taxes & fees
Oct 12 - Oct 13
Ocean View Terrace Inn
A parking lot with a building in the background.
A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.
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.

20. Clinton Motel

Clinton Motel
Clinton
$78
$90 total
includes taxes & fees
Oct 13 - Oct 14
Clinton Motel
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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 October
Typical weather for Southold
October
High 17°C / low 14°C. Sunny most days.
View properties in October
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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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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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The Old Field Vineyards

9.6/10 (5 reviews)
Travelers might want a tour of The Old Field Vineyards, just one of the places to visit, and located 1 mi (1.6 km) from central Southold.
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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 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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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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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
Horton Point Lighthouse, Southold Long Island New York as seen from above.

Check out reviews of Southold hotels guests love

Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Parking wasn’t convenient."
Carl 1-night trip
Posted 15 hours ago
Hyatt Place Long Island East End
Greenview Inn Riverhead

Greenview Inn Riverhead

10/10 Excellent
"Excellent service, clean room, humble and polite receptionist and waited until late for an late check in. Will definitely comeback 💯"
Aurora 1-night trip
Posted 15 hours ago
Greenview Inn Riverhead
The Hampton Maid

The Hampton Maid

10/10 Excellent
"excellent stay...staff was friendly. will stay here again."
Joshua 1-night trip
Posted 23 hours ago
The Hampton Maid
The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"The rooms have recently been renovated and are very well designed."
Frank 1-night trip
Posted 1 day ago
The Bentley Hotel Southampton
The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Great hotel with friendly staff, clean and comfortable rooms, and excellent service — I really enjoyed my stay!"
Antrii 1-night trip
Posted 1 day ago
The Harbor Front Inn
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"This place was great! The restaurant was delicious, the lounge was great, the room was amazing and to top it off the view from our hotel was incredible. The staff were so generous and accommodating. We went for a long weekend/anniversary celebration. I wish we stayed longer and took advantage of the rest of the amenities the hotel has to offer. We will definitely go back."
Ryan 2-night trip
Posted 2 days ago
Saybrook Point Resort & Marina
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"Great stay. The hotel was clean and convenient. Highly recommend."
Bryan 1-night trip
Posted 3 days ago
Hilton Garden Inn Riverhead
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Friendly staff. Convenient location."
Rodhmir 1-night trip
Posted 3 days ago
Pier Blue Inn Old Saybrook - Essex
The Shoals Suites and Slips

The Shoals Suites and Slips

10/10 Excellent
"The staff were all great, the food from food truck was delicious, check in was quick!"
Jena 1-night trip
Posted 7 days ago
The Shoals Suites and Slips

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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