Search Chalets in Wainscott from CA $134

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Nov 13 - Nov 15
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Nov 20 - Nov 22
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Dec 4 - Dec 6
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No exact matches found, but these alternatives could be just right

Recommended hotels in Wainscott

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

1. The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (295 reviews)
"everything about the hotel was excellent, prices fair for the Hamptons!"
United States
Jane
The price is CA $288
CA $385 total
includes taxes & fees
Nov 8 - Nov 9
The Sagaponack
A deck with wicker furniture, including a sofa and an ottoman, and a wooden railing.

2. Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
Wainscott
10.0 out of 10, Exceptional, (34 reviews)
"We loved this home and location! The home is so beautifully appointed and clean. It had everything you would ever need for a wonderful time with family and friends. The hosts were extremely responsive and easy to work with. We would go back in a heartbeat!"
United States
Suzanne B.
The price is CA $1,154
CA $2,780 total
includes taxes & fees
Nov 11 - Nov 12
Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
Terrace/patio

3. East Hampton House Resort

East Hampton House Resort
3.0 star property
East Hampton North
9.0 out of 10, Wonderful, (351 reviews)
"the place is great. the location was excellent for the film festival. The room itself was very roomy clean cute little balcony. I will book it again for the festival."
United States
Tina
The price is CA $202
CA $269 total
includes taxes & fees
Nov 10 - Nov 11
East Hampton House Resort
A two-story building with a porch and a flagpole.

4. The Maidstone

The Maidstone
4.0 star property
East Hampton
8.2 out of 10, Very good, (182 reviews)
"lovely hotel - would stay again but would ask for a back room as the noise from the very busy road is constant. Otherwise awesome amenities, loved that you had a ghd hairdryer and straighteners. Every where smelt divine! Breakfast was lovely and a decent coffee."
Australia
Clara
The price is CA $282
CA $338 total
includes taxes & fees
Nov 15 - Nov 16
The Maidstone
A building with a brick facade, a porch with steps, an American flag, and a sign with a ship and text.

5. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (685 reviews)
"The room was nicely appointed; sufficient parking; close to downtown; and a nice variety for breakfast."
United States
Annie
The price is CA $306
CA $350 total
includes taxes & fees
Nov 10 - Nov 11
Sag Harbor Inn
A silver RV with a small porch and two striped lawn chairs.

6. A Room At The Beach

A Room At The Beach
3.0 star property
Bridgehampton
9.2 out of 10, Wonderful, (105 reviews)
"We loved this place! Gorgeous, well-appointed, clean, charming, staff friendly and helpful."
United States
Annabel
The price is CA $414
CA $473 total
includes taxes & fees
Nov 10 - Nov 11
A Room At The Beach
A two-story house with a porch, outdoor seating, and a bicycle.

7. Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (210 reviews)
"Great place, convenient location, very friendly staff"
United States
Erika
The price is CA $287
CA $361 total
includes taxes & fees
Dec 6 - Dec 7
Journey East Hampton
A two-story building with a brick pathway leading to the entrance.

8. Bridgehampton Inn

Bridgehampton Inn
3.5 star property
Bridgehampton
9.4 out of 10, Exceptional, (232 reviews)
"Wonderful staff - excellent food and service"
United States
Cori
The price is CA $418
CA $477 total
includes taxes & fees
Nov 10 - Nov 11
Bridgehampton Inn
A residential property with a sign indicating it is a restaurant and inn from 1770.

9. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (172 reviews)
"Beautiful property, we had a wonderful stay. Staff were very friendly and helpful, and the location is an easy walk to shops and restaurants."
United States
Lisa
The price is CA $474
CA $648 total
includes taxes & fees
Nov 30 - Dec 1
The 1770 House Restaurant & Inn
A large, white building with a green awning, surrounded by well-maintained lawns and colorful flower beds.

10. The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (134 reviews)
"Good location"
Canada
Josie
The price is CA $471
CA $552 total
includes taxes & fees
Dec 3 - Dec 4
The Huntting Inn
A building with a black front door, a balcony with railings, a street lamp above the door, and a sign that reads 'FARWAY.'

11. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (320 reviews)
"Great location , wonderful lobby bar Cute rooms"
United States
Thomas
The price is CA $427
CA $536 total
includes taxes & fees
Dec 6 - Dec 7
Faraway Sag Harbor
A house with a sloped roof, large windows, and a pathway leading to the entrance.

12. Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (90 reviews)
"Proximity to East Hampton stores - so close you can walk to most things, biggest asset of this property. Room was nice, bedding excellent."
United States
Rhett
The price is CA $454
CA $656 total
includes taxes & fees
Nov 10 - Nov 11
Mill House Inn
A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

13. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is CA $314
CA $694 total
includes taxes & fees
Nov 11 - Nov 12
Charming Accommodations in the Hamptons
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.

14. Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.0 out of 10, Wonderful, (165 reviews)
"Incredible stay. Going back in the fall"
United States
Adam
The price is CA $830
CA $954 total
includes taxes & fees
Nov 6 - Nov 7
Topping Rose House
A large, traditional house with multiple chimneys, surrounded by a well-maintained lawn and a sand bunker.

15. Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (518 reviews)
"You can't find a nicer owner, or a more laid back conveniently located spot"
United States
Eric
The price is CA $150
CA $193 total
includes taxes & fees
Nov 10 - Nov 11
Hamlet Inn
A snow-covered pathway leading to a building with a porch.

16. Southampton Inn

Southampton Inn
3.0 star property
Southampton
8.6 out of 10, Excellent, (601 reviews)
"First time staying there, loved it. Great location, shuttle to beach, good times!"
United States
Kevin
The price is CA $279
CA $342 total
includes taxes & fees
Nov 6 - Nov 7
Southampton Inn
A white outdoor seating area with a white table and a potted plant.

17. The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (615 reviews)
"great spot to stay,"
United States
Armando
The price is CA $189
CA $216 total
includes taxes & fees
Nov 8 - Nov 9
The Bentley Hotel Southampton
A backyard with a swimming pool, lounge chairs, and umbrellas.

18. The Atlantic Hotel

The Atlantic Hotel
2.5 star property
Southampton
7.2 out of 10, Good, (1,000 reviews)
"Lots of parking, rooms were clean and smelt nice"
United States
miranda
The price is CA $145
CA $201 total
includes taxes & fees
Nov 24 - Nov 25
The Atlantic Hotel
A wooden deck with a hot tub, outdoor furniture, and a grill area.

19. Year round Jacuzzi - Blackberry East Hampton Home

Year round Jacuzzi - Blackberry East Hampton Home
East Hampton
9.2 out of 10, Wonderful, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is CA $134
CA $1,932 total
includes taxes & fees
Nov 11 - Nov 12
Year round Jacuzzi - Blackberry East Hampton Home
A house with a wooden staircase leading to a front door, surrounded by lush pink flowering bushes.

20. EHP Resort & Marina

EHP Resort & Marina
3.5 star property
East Hampton
8.0 out of 10, Very good, (11 reviews)
"just what we were looking for ! perfect"
United States
theresa
The price is CA $483
CA $607 total
includes taxes & fees
Nov 8 - Nov 9
EHP Resort & Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Learn more about Wainscott

Tucked between East Hampton and Bridgehampton, this Hamptons hamlet offers pristine beaches with gentle waves perfect for families. Rent bikes to explore Wainscott's farm stands selling local produce, then visit nearby Sag Harbour for boutique shopping and waterfront dining.

See all hotels in Wainscott
A coastal landscape with a beach, ocean waves, and a sunset sky.

Top reviews in Wainscott

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

The Sagaponack

The Sagaponack
Wainscott

10/10 Excellent

Lovely place, would stay again
Canada
Brad
Reviewed June 27, 2026
The Sagaponack

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