Hotels in Southold

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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 light blue bus with "THE SHOALS" written on the front, parked in a driveway with a house and garden in the background.
A storefront with a sign reading "THE SHOALS".
A modern living room with a blue sofa, light blue armchairs, a dining table, and a kitchen in the background.

1. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
$206
$260 total
includes taxes & fees
Nov 1 - Nov 2
The Shoals Suites and Slips
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 bathroom with a bathtub, green tiled walls, and windows with white blinds.
A bar area with stools, a shelf with glasses, and decorative plants.

2. Zey Hotel

Zey Hotel
Greenport
$203
$231 total
includes taxes & fees
Oct 25 - Oct 26
Zey Hotel
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 scene with a wooden structure, two wooden chairs, a campfire, and string lights.
A beach bar with wooden chairs and a small table, overlooking the sea.

3. Sound View Greenport

Sound View Greenport
Greenport
$199
$256 total
includes taxes & fees
Nov 16 - Nov 17
Sound View Greenport
An outdoor patio area with string lights, tables, chairs, and a fire pit.
A staircase with wooden balusters and a white wall.
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.

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 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.
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 leather armchair, a small round table with a book, and a bookshelf with books and decorative items.
A child playing with a colorful kite in a grassy field.
A neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.

6. The Harbor Front Inn

The Harbor Front Inn
Greenport
$179
$233 total
includes taxes & fees
Nov 3 - Nov 4
The Harbor Front Inn
Front of property - evening/night
Bar (on property)
Terrace/patio
Property amenity

7. Shelter Island House

Shelter Island House
Shelter Island Heights
$201
$230 total
includes taxes & fees
Oct 25 - Oct 26
Shelter Island House
Terrace/patio
Room
Living area
Beach

8. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
$212
$353 total
includes taxes & fees
Nov 9 - Nov 10
Cliffside Resort Condominiums
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 conservatory with a dining table set for four, surrounded by wooden chairs, with a view of trees and a lawn.
A serene lakeside view with two Adirondack chairs facing a calm lake, surrounded by trees and a clear sky.

9. House on Chase Creek

House on Chase Creek
The Heights
$185
$211 total
includes taxes & fees
Nov 2 - Nov 3
House on Chase Creek
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.
A dining area with a round table, chairs, a vase, and a painting on the wall.
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.

10. Oyster Estate

Oyster Estate
Greenport
$247
$311 total
includes taxes & fees
Oct 25 - Oct 26
Oyster Estate
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.
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".
A reception desk with a white backdrop, surrounded by various plants and a modern pendant light.

11. American Beech Hotel

American Beech Hotel
Greenport
$251
$327 total
includes taxes & fees
Oct 25 - Oct 26
American Beech Hotel
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 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.

12. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
$135
$154 total
includes taxes & fees
Oct 31 - Nov 1
The Bentley Hotel Southampton
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 lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

13. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
$219
$250 total
includes taxes & fees
Nov 1 - Nov 2
Sag Harbor Inn
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 tented accommodation with a bed, television, and a small table with a chair.

14. North Fork Resort

North Fork Resort
Greenport
$321
$367 total
includes taxes & fees
Oct 22 - Oct 23
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 reception area with a staircase, a framed artwork, and a reception desk with "THE MENHADEN" signage.
A modern bar area with black bar stools, a counter with a variety of bottles, and hanging green plants in wire baskets.

15. The Menhaden

The Menhaden
Greenport
$329
$416 total
includes taxes & fees
Nov 8 - Nov 9
The Menhaden
A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.
A breakfast bar with cereal, coffee, and fresh milk.
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.

16. Shorewood Inn

Shorewood Inn
Riverhead
$103
$117 total
includes taxes & fees
Oct 22 - Oct 23
Shorewood Inn
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.
Two Adirondack chairs facing a beach with a clear view of the sea and a distant island.
A window with a view of a building and trees, a small table with a lamp, and a curtain partially covering the window.

17. Ocean View Terrace Inn

Ocean View Terrace Inn
Hampton Bays
$122
$196 total
includes taxes & fees
Oct 22 - Oct 23
Ocean View Terrace 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 sign for 'The Atlantic Southampton' with a stylized logo and text.
A kitchen counter with a coffee maker, thermos, fruits, and breakfast items.
A swimming pool with lounge chairs and umbrellas, surrounded by a wooden fence and trees.

18. The Atlantic Hotel

The Atlantic Hotel
Southampton
$107
$147 total
includes taxes & fees
Oct 28 - Oct 29
The Atlantic 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 beach scene with a sunset, calm sea, and a few people fishing.
A room with a wicker sofa, a small table with a potted plant, and a bed with a wooden ladder.
A house with a covered porch, a garden with various plants and flowers, and a 'OPEN' sign on the window.

19. Hamlet Inn

Hamlet Inn
Southampton
$149
$193 total
includes taxes & fees
Oct 22 - Oct 23
Hamlet Inn
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A spacious living room with a fireplace, comfortable seating, and large windows.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.
A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.

20. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
$410
$515 total
includes taxes & fees
Nov 16 - Nov 17
Faraway Sag Harbor
View all properties
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
17°
14°
12°
8°
8°
4°
4°
0°
4°
0°
6°
2°
10°
7°
15°
12°
20°
17°
24°
21°
25°
22°
22°
19°
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.
See properties

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.
See properties

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.
See properties

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.
See properties

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.
See properties

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.
See properties

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.
See properties

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.
See properties

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

Budget Host East End

Budget Host East End

8/10 Good
"Very fri"
Mariann 1-night trip
Posted 4 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 5 hours ago
The Bentley Hotel Southampton
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Perfect location on the Sound. Beautiful resort with really nice large rooms. Wonderful dining and really a great experience!"
David 3-night trip
Posted 10 hours ago
Saybrook Point Resort & Marina
Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"."
Marcelia 1-night trip
Posted 1 day 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 1970’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 1 day 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 1 day ago
Hilton Garden Inn Riverhead
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. 😊"
Grace 1-night trip
Posted 1 day ago
The Atlantic Hotel
Sound View Greenport

Sound View Greenport

8/10 Good
"This was our third stay at Soundview. We stay there because all of the rooms face the sound and the natural view can’t be beat. The rooms are lodgy but spacious and depending on your room, there are public/private balconies."
Danielle 1-night trip
Posted 2 days ago
Sound View Greenport
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

8/10 Good
"Very clean bathroom. Very dated and weathered furniture. The linens were good. The paint on the door needed cleaned. The receptionist was very personable. We were on the first level and could hear the folks above."
kimberly 1-night trip
Posted 3 days ago
Pier Blue Inn Old Saybrook - Essex

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.

Keep exploring