Top Chalets in Hamptons in 2026

A wooden church with a steeple, surrounded by trees and a clear blue sky.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

No exact matches found, but these alternatives could be just right

Recommended hotels in Hamptons

A white outdoor seating area with a white table and a potted plant.

1. The Bentley Hotel Southampton

Southampton

Frank

Rp3.034.399 total

includes taxes & fees

6 Oct - 7 Oct

A large, traditional house with multiple chimneys, surrounded by a well-maintained lawn and a sand bunker.

2. Hamlet Inn

Southampton

Thomas

Rp4.339.350 total

includes taxes & fees

1 Oct - 2 Oct

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

3. Ocean View Terrace Inn

Hampton Bays

Timothy

Rp3.249.344 total

includes taxes & fees

1 Oct - 2 Oct

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

4. The Hampton Maid

Hampton Bays

SABINA

Rp4.170.288 total

includes taxes & fees

1 Oct - 2 Oct

A wooden deck with rows of chairs, a railing, and a view of the sea.

5. Ocean Vista Resort

Amagansett

Dan

Rp2.603.574 total

includes taxes & fees

4 Oct - 5 Oct

A residential property with a covered patio, a gravel driveway, and a fenced yard.

6. The Penny Lane

Hampton Bays

John

Rp3.959.676 total

includes taxes & fees

22 Oct - 23 Oct

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

7. Southampton Inn

Southampton

Kevin

Rp6.249.512 total

includes taxes & fees

18 Oct - 19 Oct

8. East Hampton House Resort

East Hampton North

James

Rp3.631.982 total

includes taxes & fees

28 Oct - 29 Oct

A silver RV with a small porch and two striped lawn chairs.

9. A Room At The Beach

Bridgehampton

"I absolutely loved my stay at **A Room at the Beach** in Bridgehampton. Every detail of the property feels thoughtfully designed, creating an atmosphere that is both elegant and incredibly relaxing. The rooms are stylish, comfortable, and well appointed. They strike the perfect balance between luxury and warmth. What really sets this property apart, though, are the charming grounds. They've created gathering spaces that invite you to pause, read, enjoy a morning coffee, and take in the...

Barbara

Rp6.081.778 total

includes taxes & fees

4 Oct - 5 Oct

Two bicycles with wicker baskets labeled "Sophie & Co." parked in front of a building with a dark door and white columns.

10. The Sagaponack

Wainscott

Jane

Rp5.185.437 total

includes taxes & fees

1 Oct - 2 Oct

A small, single-story house with a porch, surrounded by trees and a grassy yard.

11. Hampton's Vacation Inn

Hampton Bays

Christopher

Rp2.541.730 total

includes taxes & fees

1 Oct - 2 Oct

A two-story building with a porch, white railings, and a black door with a number.

12. The Maidstone

East Hampton

Steven

Rp5.899.634 total

includes taxes & fees

19 Oct - 20 Oct

13. Windward Shores Ocean Resort

Napeague

Gaurang J

Rp2.932.032 total

includes taxes & fees

12 Oct - 13 Oct

A building with a brick facade, a porch with steps, an American flag, and a sign with a ship and text.

14. Sag Harbor Inn

Sag Harbor

Terri

Rp5.115.279 total

includes taxes & fees

30 Oct - 31 Oct

15. Sea Crest Resort

Amagansett

Kiril

Rp3.801.628 total

includes taxes & fees

1 Oct - 2 Oct

A two-story building with a sign reading "Squiretown Rd" and a storefront with a sign that says "B&B."

16. Hampton Bays Hotel on Main

Hampton Bays

desirae

Rp2.423.903 total

includes taxes & fees

1 Oct - 2 Oct

17. Breakers Montauk

Montauk

Christine

Rp2.600.864 total

includes taxes & fees

12 Oct - 13 Oct

A modern outdoor deck with lounge chairs and a view of the beach.

18. Offshore Montauk

Montauk

Jaime

Rp4.890.542 total

includes taxes & fees

4 Oct - 5 Oct

A large, historic building with multiple stories and a prominent tower, surrounded by lush greenery and a body of water.

19. Montauk Manor

Montauk

Maria

Rp3.001.607 total

includes taxes & fees

12 Oct - 13 Oct

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

20. Bridgehampton Inn

Bridgehampton

Leslie

Rp6.141.465 total

includes taxes & fees

12 Oct - 13 Oct

View all properties

Find holiday rentals that suit your style

Aparthotels

Cottages

Save an average of 15% on thousands of hotels when you're signed in

Top Hamptons Hotel Reviews

Ocean Vista Resort

10/10 Excellent

"The beach was perfect"

Bayview Resort

10/10 Excellent

"Brian is so accommodating and cannot do enough for his guests! My boyfriend and I found this hidden treasure a year ago and never wanted to leave! It’s set on the bay and is so amazing that there are no words to describe it! It’s so clean and it’s serenity and peace like no other! The pool is so clean and it’s mineral pool, we love taking out the kayaks on gorgeous bay! The property and rooms and so clean and Brian who runs the report is so kind and cannot do enough for everyone! I cannot say enough positive words about our stay on behalf of my boyfriend and I!"

Hamlet Inn

10/10 Excellent

"The hotel location is ideal. About a 2 mile radius from the town center, shopping, attractions and beaches. The room is very comfortable where all necessary amenity items are available. We had a nice closet in the room, a refrigerator and microwave. It would have been nice to have a couple of drawers if we had stayed more than 2 nights. The shower was particularly nice! Coffe, tea, soft drinks along with a wide variety of snacks, cakes and candy bars are available the entire day."

Find out more about Hamptons

Hamptons Chalets information

Number of reviews	2,784
Accommodation	0 Chalets
Lowest Price	Rp2.423.903
Highest Price	Rp6.249.512

Explore a world of travel with Expedia

More ways to book

Book Chalets in Hamptons on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Recommended hotels in Hamptons

1. The Bentley Hotel Southampton

2. Hamlet Inn

3. Ocean View Terrace Inn

4. The Hampton Maid

5. Ocean Vista Resort

6. The Penny Lane

7. Southampton Inn

8. East Hampton House Resort

9. A Room At The Beach

10. The Sagaponack

11. Hampton's Vacation Inn

12. The Maidstone

13. Windward Shores Ocean Resort

14. Sag Harbor Inn

15. Sea Crest Resort

16. Hampton Bays Hotel on Main

17. Breakers Montauk

18. Offshore Montauk

19. Montauk Manor

20. Bridgehampton Inn

Find holiday rentals that suit your style

Top Hamptons Hotel Reviews

Ocean Vista Resort

The Hampton Maid

Bayview Resort

Hampton Bays Hotel on Main

Hampton's Vacation Inn

Hamlet Inn

Faraway Sag Harbor

The Penny Lane

Find out more about Hamptons

Hamptons Chalets information

Explore a world of travel with Expedia

Search Chalets in Hamptons

Change your mind

Treat yourself

Be picky

Check prices for these dates

Recommended hotels in Hamptons

1. The Bentley Hotel Southampton

2. Hamlet Inn

3. Ocean View Terrace Inn

4. The Hampton Maid

5. Ocean Vista Resort

6. The Penny Lane

7. Southampton Inn

8. East Hampton House Resort

9. A Room At The Beach

10. The Sagaponack

11. Hampton's Vacation Inn

12. The Maidstone

13. Windward Shores Ocean Resort

14. Sag Harbor Inn

15. Sea Crest Resort

16. Hampton Bays Hotel on Main

17. Breakers Montauk

18. Offshore Montauk

19. Montauk Manor

20. Bridgehampton Inn

Find holiday rentals that suit your style

Top Hamptons Hotel Reviews

Ocean Vista Resort

Find out more about Hamptons

Hamptons Chalets information

Explore a world of travel with Expedia