Hotels in Southold

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Check prices for these dates

Tonight
Oct 10 - Oct 11
Tomorrow
Oct 11 - Oct 12
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

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 hotel room with a bed, a sofa, a coffee table, and a view of the city.
A modern living room with a blue sofa, light blue armchairs, a dining table, and a kitchen in the background.
A storefront with a sign reading "THE SHOALS".

1. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
$269
$332 total
includes taxes & fees
Nov 1 - Nov 2
The Shoals Suites and Slips
A spacious room with wicker furniture, large windows, and a view of the sea.
A coastal building with large windows, a deck, and a view of the sea at sunset.
A beach bar with wooden chairs and a small table, overlooking 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.

2. Sound View Greenport

Sound View Greenport
Greenport
$192
$248 total
includes taxes & fees
Nov 2 - Nov 3
Sound View Greenport
A two-story house with a balcony, outdoor seating area, and a variety of plants.
A modern bedroom with two beds, a sofa, a coffee table, and a potted plant.
A restaurant with a signboard listing its hours of operation.
A bathroom with a bathtub, green tiled walls, and windows with white blinds.

3. Zey Hotel

Zey Hotel
Greenport
$203
$231 total
includes taxes & fees
Oct 12 - Oct 13
Zey Hotel
An outdoor patio area with string lights, tables, chairs, and a fire pit.
A staircase with wooden balusters and a white wall.
A large, white building with multiple windows and a prominent tree in the foreground.
A modern hotel room with a large bed, a sofa, a chair, a small table, and a mirror.

4. The Chequit

The Chequit
The Heights
$179
$205 total
includes taxes & fees
Nov 1 - Nov 2
The Chequit
A lakeside patio with outdoor seating and a view of the water.
A beach with sun loungers and umbrellas, a sandy path, and a view of the water.
Outdoor spa tub
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.

5. 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 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.'
A bar area with wooden bar stools and a bookshelf.

6. The Harbor Front Inn

The Harbor Front Inn
Greenport
$179
$233 total
includes taxes & fees
Nov 2 - Nov 3
The Harbor Front Inn
A serene landscape with a calm body of water reflecting trees with autumn foliage.
A sign for 'House on Chase Creek' with a duck illustration.
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.

7. 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
Room
Beach

8. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
$212
$353 total
includes taxes & fees
Nov 9 - Nov 10
Cliffside Resort Condominiums
Front of property - evening/night
Terrace/patio
Property amenity
Property amenity

9. Shelter Island House

Shelter Island House
Shelter Island Heights
$201
$230 total
includes taxes & fees
Oct 12 - Oct 13
Shelter Island House
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.
A modern living room with a sectional sofa, a wooden coffee table, and a large window providing a view of trees.
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.

10. Oyster Estate

Oyster Estate
Greenport
$252
$317 total
includes taxes & fees
Nov 8 - Nov 9
Oyster Estate
A modern house with a deck, outdoor seating, and a fire pit.
A tented accommodation with a bed, television, and a small table with a chair.
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.

11. North Fork Resort

North Fork Resort
Greenport
$266
$304 total
includes taxes & fees
Oct 12 - Oct 13
North Fork Resort
A waterfront property with a large house, multiple boats docked, and lush greenery.
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.
A hotel lobby with a sofa, chairs, tables, and a large window.

12. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
$219
$250 total
includes taxes & fees
Nov 1 - Nov 2
Sag Harbor Inn
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.
A building with a red facade, a green tree in front, and a sign reading "OPENSPACE".
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.

13. American Beech Hotel

American Beech Hotel
Greenport
$251
$327 total
includes taxes & fees
Oct 12 - Oct 13
American Beech Hotel
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 breakfast bar with cereal, coffee, and fresh milk.

14. Shorewood Inn

Shorewood Inn
Riverhead
$103
$117 total
includes taxes & fees
Oct 11 - Oct 12
Shorewood Inn
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.
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.
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 living room with a flat-screen TV, a dining area with a round table and chairs, a sofa with cushions, and a small side table with a lamp.

15. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
$143
$163 total
includes taxes & fees
Oct 28 - Oct 29
The Bentley Hotel Southampton
A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.
A modern reception area with a staircase, a framed artwork, and a reception desk with "THE MENHADEN" signage.
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.

16. The Menhaden

The Menhaden
Greenport
$346
$435 total
includes taxes & fees
Nov 8 - Nov 9
The Menhaden
A hotel room with a bed, bedside tables, a desk with chairs, a sofa, a window with curtains, and a door leading outside.
A swimming pool with lounge chairs and umbrellas, surrounded by a wooden fence and trees.
A hotel room with a bed, bedside tables, a desk with a chair, and a window with a view of greenery.
A sign for 'The Atlantic Southampton' with a stylized logo and text.

17. The Atlantic Hotel

The Atlantic Hotel
Southampton
$107
$147 total
includes taxes & fees
Oct 28 - Oct 29
The Atlantic Hotel
A parking lot with a building in the background.
A rectangular swimming pool with a fenced area, surrounded by trees and a concrete deck with white metal loungers.
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.

18. Clinton Motel

Clinton Motel
Clinton
$78
$90 total
includes taxes & fees
Oct 13 - Oct 14
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 window with a view of a building and trees, a small table with a lamp, and a curtain partially covering the window.
A house with a dark blue exterior, a white porch railing, and a red door.
A bedroom with a bed, a desk, a chair, a window with a view of trees and a body of water.

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 pool area with umbrellas, potted plants, and a pathway leading to a building.
A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.
A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.
A spacious living room with a fireplace, comfortable seating, and large windows.

20. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
$420
$528 total
includes taxes & fees
Nov 8 - Nov 9
Faraway Sag Harbor
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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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Custer Institute and Observatory

Custer Institute and Observatory is 1 mi (1.6 km) from central Southold, why not stop by during your stay. If you have fun at Custer Institute and Observatory, you'll love 8 Hands Farm and Railroad Museum of Long Island, both 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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McCabe's Beach

When the beach is calling your name, you might want to head down to McCabe's Beach, located 1.6 mi (2.5 km) from central Southold. If you want to continue walking by the waves, head to Horton Lane 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
A coastal landscape with a white church on a grassy hill, overlooking a sandy beach and the ocean.

Check out reviews of Southold hotels guests love

Sound View Greenport

Sound View Greenport

8/10 Good
"There is no room to put anything in the bathroom. If u want lunch you have to leave the property. No food is available until 5. After a 3 and a half hour trip The last thing I wanted to do was get into the car again"
Angela 1-night trip
Posted 2 hours ago
Sound View Greenport
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

8/10 Good
"Staff were very helpful, they printed some documents for me at the front desk. And, my room had reading lights over the bed. May not matter to most, but those lights are great for those of us who like to read in bed."
Darla 1-night trip
Posted 3 hours ago
Hilton Garden Inn Riverhead
Shorewood Inn

Shorewood Inn

10/10 Excellent
"Beautiful hotel vintage"
Dennis 1-night trip
Posted 5 hours ago
Shorewood Inn
Zey Hotel

Zey Hotel

10/10 Excellent
"Small issues I hope they fixed"
Vincenzo 2-night trip
Posted 6 hours ago
Zey Hotel
Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent
"We were pleased with the excellent location to Sag Harbor's Main Street and the Zagaya restaurant *upstairs. It was superb! The staff was very friendly and helpful. The rooms were small and the baths particularly small so just a heads up on that although the toiletries were really nice. The hotel has a great vibe at night with live music in the bar area on Thursday evenings. The weather was cool...absolutely gorgeous for early October so we didn't use the pool/cabanas (although it was heated). I did peek in the fitness room and it was very nice. Not enough time to check out the spa but there's always next time!"
SUSAN 4-night trip
Posted 22 hours ago
Faraway Sag Harbor
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

10/10 Excellent
"The hotel is not new but was clean and everything worked well. The staff was very friendly and helpful. Breakfast was excellent and the hotel price was very reasonable."
Edward 1-night trip
Posted 2 days ago
Quality Inn Old Saybrook - Westbrook
Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Parking wasn’t convenient."
Carl 1-night trip
Posted 4 days ago
Hyatt Place Long Island East End
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 5 days ago
The Harbor Front Inn
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 10 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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