Hampton Bays Vacation Homes

A sandy beach path with wooden fences on either side leading to the ocean.

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Our top choices for Hampton Bays holiday homes

A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

1. Jacuzzi year-round - Villa Luz Private Home

Hampon Bays

Annie B.

HK$13,074 total

includes taxes & fees

12 Oct - 13 Oct

A modern building with large windows overlooking a beach.

2. Beachfront Jacuzzi All Year - Black Swan Home

Hampton Bays

Donald J.

HK$9,679 total

includes taxes & fees

12 Oct - 13 Oct

A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

3. Immaculate Waterfront 2 bedroom!

Hampton Bays

Michael L.

HK$4,483 total

includes taxes & fees

12 Oct - 13 Oct

A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

4. Elegant 5-Bedroom Hamptons Home with Private Pool

Hampton Bays

Judith M.

HK$7,684 total

includes taxes & fees

12 Oct - 13 Oct

A modern kitchen with white cabinets, a dining area with a round table, and a living area with a sofa and decorative pillows.

5. Cozy Hamptons Escape 3BR Minutes From Beach!

Hampton Bays

Taylor H.

HK$12,247 total

includes taxes & fees

12 Oct - 13 Oct

A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

6. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Southampton

Justin

HK$4,725 total

includes taxes & fees

13 Oct - 14 Oct

7. Prime location, walk to all, cozy cottage Westhampton Beach

Westhampton Beach

Chris J.

HK$5,891 total

includes taxes & fees

19 Oct - 20 Oct

A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

8. Minutes from the beach, brand new 4 bedroom

Southampton

Okito H.

HK$8,401 total

includes taxes & fees

12 Oct - 13 Oct

A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

9. The SandPiper

Pipes Cove

Julian V.

HK$1,937 total

includes taxes & fees

2 Nov - 3 Nov

A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

10. Aqua Vista

Pipes Cove

Kerri L.

HK$1,990 total

includes taxes & fees

9 Nov - 10 Nov

A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

11. Amazing Southampton Home with Private Heated Pool

Southampton

Serina R.

HK$10,063 total

includes taxes & fees

19 Oct - 20 Oct

A modern living room with a grey sofa, round coffee table, and a white fireplace.

12. 5 Bedrooms! 4 Min to the Beach! HEATED POOL!

Westhampton Beach

Matthew M.

HK$21,285 total

includes taxes & fees

12 Oct - 13 Oct

A modern living room with a sofa, armchairs, a coffee table, and a TV.

13. Minutes from the beach, brand new 3 bedroom

Southampton

Kathy B.

HK$8,894 total

includes taxes & fees

2 Nov - 3 Nov

A wooden house with a front porch, white railings, and a double door.

14. COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

Southampton

Melissa

HK$22,919 total

includes taxes & fees

12 Oct - 13 Oct

A beach with people relaxing, a pier extending into the water, and a clear sky.

15. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Pipes Cove

Callie E.

HK$3,022 total

includes taxes & fees

1 Nov - 2 Nov

A rocky beach with clear water and a forested hillside in the background.

16. North Fork Fall Escape—Vineyards, Apple Picking & Greenport

Mattituck

Glenn F.

HK$9,836 total

includes taxes & fees

24 Oct - 25 Oct

A spacious living area with a fireplace, a wooden staircase, and large windows.

17. Cozy beach hose minutes from Hamptons

Calverton

Robin M.

HK$5,648 total

includes taxes & fees

19 Oct - 20 Oct

A modern kitchen with white cabinets, a stainless steel sink, and a dishwasher.

18. Newly Renovated Pristine Southampton Colonial

Southampton

Brian M.

HK$13,037 total

includes taxes & fees

11 Nov - 12 Nov

A wooden pathway leading to a beach with scattered rocks and greenery.

19. Beach Block Hideaway

Pipes Cove

Teresa C.

HK$3,533 total

includes taxes & fees

3 Nov - 4 Nov

An outdoor dining area with hanging lights, palm trees, and a bar.

20. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

HK$2,403 total

includes taxes & fees

12 Oct - 13 Oct

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Top Hampton Bays Hotel Reviews

The Hampton Maid

10/10 Excellent

"Beautiful property. Lovely rooms."

Hampton Bays Hotel on Main

10/10 Excellent

"This hotel was clean, comfy and reasonably priced. Everything worked out well virtually checking in and was perfect for our one night stay. Parking was a little nerve racking since there was no parking on the premise but the street parking worked out well reading the street signs and moving the car when necessary."

Sun, Sky, Beach! Beautiful Waterfront home with Hot Tub, Game Room, and More!

10/10 Excellent

"Four of us decided to play golf on the eastern end of LI in late summer 2026. We rented this house in Hampton Bays. The location is terrific and our backyard was right on the Shinnecock Canal. You can't get a more peaceful, wonderful setting. The accommodations were good too, including the ping pong table which led to a tournament of champions showcasing that we all needed some serious practice! Most importantly though the owner of the house was fantastic. Reggie is responsive, accommodating and really great to work with. He gets an A. Thank you, Reggie!If you're looking for a peaceful getaway, we would recommend renting Reggie's house in Hampton Bays."

Find out more about Hampton Bays