Village of Southampton Holiday Rentals, Southampton: Private House Rentals

A wooden boardwalk leading through tall grass towards a body of water.

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Go beyond your typical stay in Village of Southampton

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Our top choices for Village of Southampton hotels

A banquet hall with round tables set for dining, each with candles, glassware, and floral centerpieces.

A snow-covered pathway leading to a building with a porch.

1. Southampton Inn

Southampton

Kevin

฿6,717

฿8,221 total

includes taxes & fees

1 Nov - 2 Nov

A staircase with a white railing, a white chandelier, and framed artwork on the walls.

Two wine bottles with labels on a counter.

A covered outdoor seating area with white canopies and brown furniture.

A dining area with tables set for guests, a fireplace, and large colorful paintings on the walls.

2. Harpoon House

Southampton

Yuliya V

฿9,068

฿10,360 total

includes taxes & fees

22 Oct - 23 Oct

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 hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.

3. The Bentley Hotel Southampton

Southampton

Armando

฿4,534

฿5,180 total

includes taxes & fees

31 Oct - 1 Nov

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 swimming pool with a white fence, a table with chairs, and a building with a white picket fence in the background.

4. Southampton Long Island Hotel

Southampton

William

฿5,340

฿6,368 total

includes taxes & fees

26 Oct - 27 Oct

A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.

A bar area with shelves stocked with various bottles and glasses.

A modern hotel room with a bed, bedside table, and a view of the garden.

A bar setting with a bartender and a customer. The bar has shelves with various bottles and glasses. There is a cushioned bench in the foreground.

5. Topping Rose House

Bridgehampton

Adam

฿21,007

฿24,119 total

includes taxes & fees

22 Oct - 23 Oct

A modern kitchen with a central island, bar stools, pendant lighting, and a seating area with a sofa and coffee table.

A modern living room with a stone wall, a flat-screen TV mounted above a door, a dark sofa, and a glass coffee table with a vase of flowers.

A two-story house with a windmill on the roof, a balcony, and three Adirondack chairs in the front yard.

A beach with sand and sparse vegetation.

6. The Hampton Maid

Hampton Bays

Joshua

฿7,103

฿8,115 total

includes taxes & fees

22 Oct - 23 Oct

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 swimming pool with lounge chairs and umbrellas, surrounded by a wooden fence and trees.

7. The Atlantic Hotel

Southampton

miranda

฿3,597

฿4,949 total

includes taxes & fees

29 Oct - 30 Oct

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 spacious living room with a white sofa, a coffee table, and a fireplace. There are large windows offering a view of the outdoors.

A house with a covered porch, a garden with various plants and flowers, and a 'OPEN' sign on the window.

A room with a wicker sofa, a small table with a potted plant, and a bed with a wooden ladder.

8. Hamlet Inn

Southampton

Eric

฿4,507

฿5,825 total

includes taxes & fees

22 Oct - 23 Oct

A conservatory with a sofa, chairs, a small table, and a view of houses.

A sunlit room with a glass ceiling, a sofa, chairs, a table, and a view of the outside.

A bedroom with a bed, two bedside tables, a window with curtains, a wall-mounted lamp, and a framed picture.

A beach with waves crashing onto the shore.

9. The Penny Lane

Hampton Bays

Jacob

฿5,414

฿6,185 total

includes taxes & fees

2 Nov - 3 Nov

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 house with a dark blue exterior, a white porch railing, and a red door.

A window with a view of a building and trees, a small table with a lamp, and a curtain partially covering the window.

10. Ocean View Terrace Inn

Hampton Bays

james

฿3,686

฿6,060 total

includes taxes & fees

22 Oct - 23 Oct

A dining area with a fireplace, bookshelves, and a view of the bar area.

A room with two armchairs, a small table with a vase of flowers, and a patterned rug.

An outdoor wedding setup with white chairs, a table with floral arrangements, and a white canopy.

A two-story building with a brick pathway leading to the entrance.

11. Bridgehampton Inn

Bridgehampton

Leslie

฿10,042

฿11,473 total

includes taxes & fees

22 Oct - 23 Oct

A tented area with a pool view, wooden lounge chairs, and a table with a drink and food.

A cozy room with a large window, a sofa, a small table with a tray, and a pair of slippers on the floor.

A beach chair with a towel labeled "CANOE PLACE" and a wicker basket with bottles and a container on the sand.

12. Canoe Place Inn and Cottages

Hampton Bays

Corrado

฿15,953

฿19,320 total

includes taxes & fees

26 Oct - 27 Oct

A waterfront property with a large house, multiple boats docked, and lush greenery.

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.

A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

13. Sag Harbor Inn

Sag Harbor

Terri

฿7,355

฿8,403 total

includes taxes & fees

1 Nov - 2 Nov

A row of bicycles parked along a path in a park-like setting with trees and a building in the background.

A bathtub surrounded by candles and flower petals.

An outdoor dining area with a table and chairs, surrounded by tall trees and string lights.

14. A Room At The Beach

Bridgehampton

Samantha

฿9,945

฿11,361 total

includes taxes & fees

25 Oct - 26 Oct

Two people standing on a deck with a view of a lake and greenery.

A pool area with lounge chairs and a deck overlooking a lake.

A spacious dining area with large windows offering a view of the outdoors. There are multiple tables and chairs arranged for dining.

A sign for Bayview Resort with a contact number.

15. Bayview Resort

Hampton Bays

Hanna

฿5,441

฿6,216 total

includes taxes & fees

22 Oct - 23 Oct

A modern hotel room with a large bed, a framed picture on the wall, and a wooden floor.

A spacious room with wooden flooring, a bar area with stools, and large windows allowing natural light.

A compact kitchen with white cabinetry, a built-in dishwasher, and a coffee maker on the countertop.

A spacious bar area with a long counter and multiple stools, a brick wall with a mural, and exposed pipes on the ceiling.

16. Hampton Bays Hotel on Main

Hampton Bays

Richard

฿3,963

฿4,527 total

includes taxes & fees

26 Oct - 27 Oct

A building with a wooden exterior and a small porch, surrounded by a well-maintained lawn and a hedge.

A well-maintained lawn in front of a building with a brick facade, multiple windows, and outdoor seating.

An outdoor dining area with a table and chairs under a tent, surrounded by a chain-link fence and a street in the background.

A person standing on a beach, looking at a smartphone.

17. Sea Haven Resort Motel

Southampton

Urvashi

฿3,909

฿5,002 total

includes taxes & fees

2 Nov - 3 Nov

A marina with boats docked, a globe sculpture, wicker furniture, and a bottle of wine on a table.

A marina with boats docked, a fire feature, and outdoor seating with a bottle and glasses.

A dining area with wooden paneling, a patterned floor, and a view of outdoor seating through large windows.

A modern hotel with a glass facade, a covered entrance, and a sign indicating it is a Hyatt Place.

18. Hyatt Place Long Island East End

Riverhead

Timothy

฿4,265

฿4,873 total

includes taxes & fees

3 Nov - 4 Nov

A hotel room with a gray sofa, a blue ottoman, a wooden desk, and a bed with white linens.

A coffee station with two coffee machines and a variety of coffee pods and cups.

A breakfast area with a sign that reads 'GOOD MORNING' and another that says 'HOT FOOD'. There are also signs for 'EGG-XACTLY' and 'GO AHEAD. PANCAKE MY DAY.' with a flowchart.

A conference room with multiple tables and chairs, equipped with water bottles, a projector screen, and a large window.

19. Holiday Inn Express & Suites Riverhead - Long Island by IHG

Riverhead

LUIS

฿4,400

฿5,027 total

includes taxes & fees

25 Oct - 26 Oct

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 white closet with shelves, a robe hanging on a wooden hanger, and a pair of black straps on a rack.

A reception desk with a vase of flowers, a sign that says "STAY awhile", and a window with blinds.

20. Shorewood Inn

Riverhead

Dennis

฿3,448

฿3,939 total

includes taxes & fees

22 Oct - 23 Oct

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Stay near popular Village of Southampton attractions

A beach with sand dunes and a person walking along the shore.

Cooper's Beach

9.2/10 (171 reviews)

Escape NYC to play in the waves, sunbathe on fine, white sands or stroll past the exclusive mansions that line the dunes of one of the best beaches in the Hamptons.

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A red house and a wooden shop with a sign reading "The Carpenter's Shop".

Southampton Historical Museum

8.6/10 (13 reviews)

Catch a glimpse of Southampton’s pioneering days in the town’s charming collection of artisan workshops and colonial buildings full of English-style furniture.

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A man carrying a woman in front of a pool with two American flags, surrounded by greenery and a monument.

Southampton Cultural Center

8.2/10 (11 reviews)

Enjoy a stop at Southampton Cultural Center, an entertaining place to visit in Village of Southampton. While you're in the area, stroll along the beautiful beaches.

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A historical homestead with a wooden exterior, a brick chimney, and a signboard detailing its history.

Halsey House

7.6/10 (7 reviews)

You can spend time studying the exhibits at Halsey House during your travels in Village of Southampton. While you're in the area, stroll along the beautiful beaches.

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Agawam Park

8.6/10 (10 reviews)

Explore the great outdoors at Agawam Park, a lovely green space in Village of Southampton. While you're in the area, stroll along the beautiful beaches.

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North Main Street Historic District

9.4/10 (12 reviews)

You can find out about the history of Village of Southampton with a stop at North Main Street Historic District. Make some time to visit the monuments while you're in the area.

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Southampton Arts Center

8.8/10 (30 reviews)

Enjoy a stop at Southampton Arts Center, an entertaining place to visit in Village of Southampton. While you're in the area, stroll along the beautiful beaches.

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Shinnecock East County Park

8.0/10 (4 reviews)

Explore the great outdoors at Shinnecock East County Park, a lovely green space in Village of Southampton. While you're in the area, stroll along the beautiful beaches.

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Learn more about Village of Southampton

Elegant estates and pristine beaches await in this historic Hamptons haven where Cooper's Beach offers perfect Atlantic swimming. Dive into local culture at Southampton Historical Museum and Arts Centre, then browse upscale boutiques along Main Street's tree-lined pavements.

See all hotels in Village of Southampton

A welcome sign for the village of Southampton, established in 1640, with a cyclist on the road.

Top Village of Southampton Hotel Reviews

Budget Host East End

8/10 Good

"Very fri"

The Bentley Hotel Southampton

10/10 Excellent

"Gorgeous room! Felt like we were home"

Sag Harbor Inn

10/10 Excellent

"The hotel was beautiful. The room was very spacious and comfortable. The continental breakfast offered many choices, and they had coffee, tea and hot chocolate available 24 hours a day."

Hyatt Place Long Island East End

10/10 Excellent

"."

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!"

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 don’t have to go down the street to get something to eat . Honestly it’s not even an issue we will continue to stay here because it is a very nice 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. 😊"

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."

Greenview Inn Riverhead

10/10 Excellent

"Inn is in a rural areas, along scenic country nestled in nature-immersed Riverhead town.Close to Riverheads amazing stores and popular eatery s They offer a more personal, relaxed atmosphere, often featuring a cozy bed rather than a corporate polish.. Great for a short business trip or as a overnite . Unique Inn atmosphere."