A calm lake with a forest in the background during sunset.

Southold hotels from RM384

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Check prices for these dates

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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Our top choices for Southold hotels

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.
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 living room with a blue sofa, light blue armchairs, a dining table, and a kitchen 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
United States
Masayo
RM757
RM967 total
includes taxes & fees
1 Nov - 2 Nov
The Shoals Suites and Slips
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 bar area with stools, a shelf with glasses, and decorative plants.
A modern bedroom with two beds, a sofa, a coffee table, and a potted plant.

2. Zey Hotel

Zey Hotel
Greenport
United States
Renee
RM744
RM850 total
includes taxes & fees
25 Oct - 26 Oct
Zey Hotel
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

3. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Keith
RM1,143
RM1,306 total
includes taxes & fees
1 Nov - 2 Nov
Silver Sands Motel & Beach Bungalows
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 spacious room with large windows, a wooden bench, yoga mats, and a door leading to a balcony with a view of the sea.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.

4. Sound View Greenport

Sound View Greenport
Greenport
United States
Christine
RM731
RM952 total
includes taxes & fees
16 Nov - 17 Nov
Sound View Greenport
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 neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.
A kitchen counter with a bottle of wine, a glass, and a basket of snacks.

5. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
Antrii
RM731
RM952 total
includes taxes & fees
4 Nov - 5 Nov
The Harbor Front 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 dining area with a round table, chairs, a vase, and a painting on the wall.
A wooden wall with a wall-mounted lamp, a shelf with decorative items, and a bedside table with a pillow.

6. Oyster Estate

Oyster Estate
Greenport
United States
Allison
RM919
RM1,157 total
includes taxes & fees
25 Oct - 26 Oct
Oyster Estate
Terrace/patio
Room
Beach
Room

7. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
William
RM690
RM1,241 total
includes taxes & fees
12 Nov - 13 Nov
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 tented accommodation with a bed, television, and a small table with a chair.
A modern living room with a sofa, a dining table, and a kitchen area in the background.

8. North Fork Resort

North Fork Resort
Greenport
United States
Altynai
RM1,312
RM1,499 total
includes taxes & fees
22 Oct - 23 Oct
North Fork Resort
Front of property โ€“ evening/night
Property amenity
Bar (on property)
Terrace/patio

9. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
RM822
RM939 total
includes taxes & fees
25 Oct - 26 Oct
Shelter Island House
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 modern living room with a grey sofa, black and white patterned rug, and a coffee table.
A modern bar area with black bar stools, a counter with a variety of bottles, and hanging green plants in wire baskets.

10. The Menhaden

The Menhaden
Greenport
United States
Daniel
RM1,343
RM1,697 total
includes taxes & fees
8 Nov - 9 Nov
The Menhaden
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.
An outdoor dining area with tables and chairs, string lights, and hanging lanterns.
A building with a red facade, a green tree in front, and a sign reading "OPENSPACE".

11. American Beech Hotel

American Beech Hotel
Greenport
United States
Mary
RM1,024
RM1,333 total
includes taxes & fees
25 Oct - 26 Oct
American Beech Hotel
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 modern hotel room with a large bed, a sofa, a chair, a small table, and a mirror.
A large, multi-story building with a porch and outdoor seating area, featuring multiple windows and a balcony.

12. The Chequit

The Chequit
The Heights
United States
Patrick
RM731
RM835 total
includes taxes & fees
1 Nov - 2 Nov
The Chequit
A serene landscape with a calm body of water reflecting trees with autumn foliage.
A house with a porch, a sign reading "House on Chase Creek," and a tree with red leaves.
A serene lakeside view with two Adirondack chairs facing a calm lake, surrounded by trees and a clear sky.
A conservatory with a dining table set for four, surrounded by wooden chairs, with a view of trees and a lawn.

13. House on Chase Creek

House on Chase Creek
The Heights
United States
Tracey
RM755
RM862 total
includes taxes & fees
2 Nov - 3 Nov
House on Chase Creek
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 swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.

14. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Terri
RM894
RM1,021 total
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.
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.
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.

15. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
United States
Armando
RM551
RM630 total
includes taxes & fees
31 Oct - 1 Nov
The Bentley Hotel Southampton
A bedroom with a bed, bedside table, lamp, and a view of the outdoors through a window.
A living room with a wooden entertainment center, a sofa, a coffee table, and a lamp.
A living room area with a sofa, a dining table, and a separate queen bedroom.
A covered patio area with outdoor seating, a potted plant, and a well-maintained lawn.

16. Southampton Long Island Hotel

Southampton Long Island Hotel
Southampton
United States
William
RM649
RM774 total
includes taxes & fees
22 Oct - 23 Oct
Southampton Long Island Hotel
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 hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.

17. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Thomas
RM1,506
RM1,893 total
includes taxes & fees
16 Nov - 17 Nov
Faraway Sag Harbor
A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.
A bedroom with a bed, a door, and a framed picture on the wall.
A breakfast bar with cereal, coffee, and fresh milk.
A reception desk with a vase of flowers, a sign that says "STAY awhile", and a window with blinds.

18. Shorewood Inn

Shorewood Inn
Riverhead
United States
Kathleen
RM419
RM479 total
includes taxes & fees
22 Oct - 23 Oct
Shorewood Inn
A dining area with a fireplace, bookshelves, and a view of the bar area.
A two-story building with a brick pathway leading to the entrance.
A room with two armchairs, a small table with a vase of flowers, and a patterned rug.
A bedroom with a wooden headboard, a bedside table with a lamp, and a bed with a grey blanket.

19. Bridgehampton Inn

Bridgehampton Inn
Bridgehampton
United States
Leslie
RM1,221
RM1,395 total
includes taxes & fees
22 Oct - 23 Oct
Bridgehampton Inn
An outdoor dining area with a table and chairs, surrounded by tall trees and string lights.
Beach
A bathtub surrounded by candles and flower petals.
A bedroom with two beds, a ceiling fan, a large window, and a view of greenery outside.

20. A Room At The Beach

A Room At The Beach
Bridgehampton
United States
Samantha
RM1,209
RM1,381 total
includes taxes & fees
22 Oct - 23 Oct
A Room At The Beach
View all properties

Hotels recommended for families in Southold

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 spacious room with large windows, a wooden bench, yoga mats, and a door leading to a balcony with a view of the sea.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.

Sound View Greenport

Sound View Greenport
Greenport
RM731
RM952 total
includes taxes & fees
16 Nov - 17 Nov
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

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
RM1,143
RM1,306 total
includes taxes & fees
1 Nov - 2 Nov
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 neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.
A kitchen counter with a bottle of wine, a glass, and a basket of snacks.

The Harbor Front Inn

The Harbor Front Inn
Greenport
RM731
RM952 total
includes taxes & fees
4 Nov - 5 Nov
The Harbor Front Inn
Terrace/patio
Room
Beach
Room

Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
RM690
RM1,241 total
includes taxes & fees
12 Nov - 13 Nov
Cliffside Resort Condominiums
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 modern hotel room with a large bed, a sofa, a chair, a small table, and a mirror.
A large, multi-story building with a porch and outdoor seating area, featuring multiple windows and a balcony.

The Chequit

The Chequit
The Heights
RM731
RM835 total
includes taxes & fees
1 Nov - 2 Nov
The Chequit
Front of property โ€“ evening/night
Property amenity
Bar (on property)
Terrace/patio

Shelter Island House

Shelter Island House
Shelter Island Heights
RM822
RM939 total
includes taxes & fees
25 Oct - 26 Oct
Shelter Island House
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 tented accommodation with a bed, television, and a small table with a chair.
A modern living room with a sofa, a dining table, and a kitchen area in the background.

North Fork Resort

North Fork Resort
Greenport
RM1,312
RM1,499 total
includes taxes & fees
22 Oct - 23 Oct
North Fork Resort
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 dining area with a round table, chairs, a vase, and a painting on the wall.
A wooden wall with a wall-mounted lamp, a shelf with decorative items, and a bedside table with a pillow.

Oyster Estate

Oyster Estate
Greenport
RM919
RM1,157 total
includes taxes & fees
25 Oct - 26 Oct
Oyster Estate
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Stay near popular Southold attractions

Sparkling Pointe

8.8/10 (11 reviews)
Sparkling Pointe crafts exquisite sparkling wines using traditional Mรฉthode Champenoise in their Southold vineyard. Savour their diverse bubblies in an elegant tasting room with vineyard views.
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Croteaux Vineyards

10.0/10 (12 reviews)
America's only all-rosรฉ vineyard offers a taste of Provence in New York's North Fork. Savour wine flights in the picturesque garden setting, complete with rustic barn and seaside charm.
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Sannino's Bella Vita Vineyard

9.6/10 (4 reviews)
This intimate vineyard offers personalised expert-guided wine tastings amid sustainable vineyards. Experience their unique White Merlot overlooking scenic North Fork landscapes or stay at their on-site B&B.
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Osprey's Dominion

9.6/10 (5 reviews)
This award-winning North Fork winery showcases sustainable viticulture through distinctive Sauvignon Blanc and Merlot offerings. Enjoy tastings on their spacious lawn with weekend live music and picnic areas.
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The Old Field Vineyards

9.6/10 (5 reviews)
This family-owned vineyard, Long Island's oldest continuously operated winery, offers handcrafted wines in a rustic setting. Enjoy tastings on expansive lawns overlooking Southold Bay.
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Custer Institute and Observatory

Long Island's oldest public observatory invites you to explore the cosmos through powerful telescopes every Saturday night. Enjoy guided stargazing at this historic astronomical sanctuary established in 1927.
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McCabe's Beach

Why not spend a lazy afternoon at McCabe's Beach during your trip to Southold? Stroll along the beaches or discover the area's sunsets.
See properties

Horton Point Park

9.4/10 (3 reviews)
This 1857 lighthouse stands sentinel over Long Island Sound, housing a nautical museum filled with maritime artefacts. Climb to the top for panoramic views, then follow the nature trail to the peaceful rocky beach below.
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Learn more about Southold

Vineyards and farm stands dot the landscape of this North Fork gem, inviting visitors to sample local wines and fresh produce. Stroll along the pebble beaches, explore historic lighthouses, or take a ferry to nearby Shelter Island for a day trip.

See all hotels in Southold
A coastal landscape with a white church on a grassy hill, overlooking a sandy beach and the ocean.

Top Southold Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"I stayed twice and borh rooms were decorated uniquely. The staff and owners were very nice. Good people"
David 1-night trip
Posted 2 hours ago
Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

8/10 Good
"Great ocean sounds through the pen window!"
Eric 3-night trip
Posted 2 hours ago
Sound View Greenport
Budget Host East End

Budget Host East End

8/10 Good
"Very fri"
Mariann 1-night trip
Posted 20 hours ago
Budget Host East End
The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Gorgeous room! Felt like we were home"
Irene 4-night trip
Posted 21 hours ago
The Bentley Hotel Southampton
Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"."
Marcelia 1-night trip
Posted 2 days ago
Hyatt Place Long Island East End
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

8/10 Good
"Room was spacious, comfortable and clean. Overall the hotel was nice. The decorating was a bit off putting and looked like it had been done in the 1970โ€™s and never changed; orange and avocado green with brown carpet. If you can get past that it was a good place to stay. Breakfast was very nice with plenty of hot and cold choices. For me, the fact that it was open from 7:30 til 10 am was very nice. I would stay here again."
Brenda 4-night trip
Posted 2 days ago
Quality Inn Old Saybrook - Westbrook
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"This hotel was so conveniently located on a main road, right off the 495, near so many restaurants and stores and a few minute drive to the wineries and farms. The property was spotless and very nice and accommodating. We had a 2 queen room for a family of 4 and it was perfectly spacious. We have small kids so we used the pool and hot tub. The pool was a little too cold for my liking but my kids had a blast. The hotel was great all around. I am sure we will be back again next fall!"
Jenna 1-night trip
Posted 2 days ago
Hilton Garden Inn Riverhead
The Harbor Front Inn

The Harbor Front Inn

8/10 Good
"The room was clean and the staff is always wonderful. Parking was a nightmare because of the festival which had nothing to do with the hotel. My only issue is the breakfast , I wish it had a little more so I donโ€™t have to go down the street to get something to eat . Honestly itโ€™s not even an issue we will continue to stay here because it is a very nice hotel"
Barbara 1-night trip
Posted 2 days ago
The Harbor Front Inn
The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"We were 4 girls and the room was two bedrooms and another bed also so it accommodated all of us. ๐Ÿ˜Š"
Grace 1-night trip
Posted 2 days ago
The Atlantic Hotel

More cheap stays in Southold

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
RM334
RM384 total
15 Nov - 16 Nov
includes taxes & fees
8/10 Very good! (1,001 reviews)
Pier Blue Inn Old Saybrook - Essex
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
RM363
RM415 total
22 Oct - 23 Oct
includes taxes & fees
6.8/10 (902 reviews)
Budget Host East End
Greenview Inn Riverhead

Greenview Inn Riverhead

1433 W Main St Riverhead NY
RM470
RM536 total
1 Nov - 2 Nov
includes taxes & fees
7.6/10 Good! (894 reviews)
Greenview Inn Riverhead
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
RM437
RM602 total
28 Oct - 29 Oct
includes taxes & fees
7.2/10 Good! (1,005 reviews)
The Atlantic Hotel
The Bentley Hotel Southampton

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY
RM551
RM630 total
31 Oct - 1 Nov
includes taxes & fees
9.6/10 Exceptional! (604 reviews)
The Bentley Hotel Southampton
The Hampton Maid

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY
RM863
RM987 total
22 Oct - 23 Oct
includes taxes & fees
9.2/10 Wonderful! (808 reviews)
The Hampton Maid

Frequently asked questions

Where is the best place to stay in Southold?
The Shoals Suites and Slips is one of the top choices for your stay based on our traveller data. This hotel offers a restaurant and private balconies. Other good choices for your stay in the area are Pier Blue Inn Old Saybrook - Essex and Water's Edge Resort & Spa. See all available top hotels, or vacation rentals in Southold.
If I need to cancel my hotel reservation in Southold, will I receive a refund?
Yes, most hotel bookings are fully refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Southold.
What's the best dog-friendly accommodation option in Southold?
White Blossom House Inn is a top hotel for people travelling with their pets, and offers free use of bicycles and in-room kitchens for its human guests. See more pet-friendly hotel accommodations in Southold.
What are some accommodation options with pools in Southold?
Water's Edge Resort & Spa: Features a seasonal outdoor pool, an indoor pool and a private beach. Sound View Greenport and The Atlantic Hotel are a couple of other choices that offer an on-site pool. View all hotels with pools in Southold.
What's it like to stay in Southold?
Visitors can enjoy all that Southold has to offer, including the wineries, beaches and gardens. Tourists can also enjoy the city's football games and monuments. In Southold, there are 141 hotels and other accommodation options to choose from. Find out more about Southold.
What should I do while I'm visiting Southold?
The picturesque setting of McCabe's Beach and Horton Lane Beach exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Sparkling Pointe and Croteaux Vineyards. Take a look at what more there is to see and do in Expedia's Southold guide.
What's the best way to get around Southold?
To see more of the larger area, hop aboard a train at Southold Station. If you want to venture out around the area, you may want a rental car in Southold for your journey.
What's the weather like in Southold?
The hottest months are usually August and July, with an average temperature of 21ยฐC, while the coldest months are January and February, with an average of 3ยฐC. Average annual precipitation for Southold is 1452 mm.

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