A coastal landscape with a beach, ocean waves, and a sunset sky.

Search Vacation Homes in Wainscott

  • 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
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Wainscott holiday homes

Beach nearby, sun-loungers, beach towels

Central Private Pool Bridgehampton home

Central Private Pool Bridgehampton home
Sag Harbor
10.0 out of 10, Exceptional, (4 reviews)
"The house and property were so nice. We have a 10 and 11 year old. They played outside or were swimming in the pool the entire time. It's close to great shopping and beaches. It was a very relaxing and enjoyable long weekend. Everything was perfect!"
United States
Heather M.
The price is HK$15,016
HK$21,421 total
includes taxes & fees
24 Jul - 25 Jul
Central Private Pool Bridgehampton home
Interior

Chic Modern Retreat in the Heart of EH! Pool Open!

Chic Modern Retreat in the Heart of EH! Pool Open!
East Hampton
10.0 out of 10, Exceptional, (13 reviews)
"Great location and amenities. "
Canada
Bryan A.
The price is HK$23,517
HK$36,409 total
includes taxes & fees
7 Aug - 8 Aug
Chic Modern Retreat in the Heart of EH! Pool Open!
Dining

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
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 HK$2,533
HK$12,441 total
includes taxes & fees
26 Jul - 27 Jul
BlackBerry Private home with jacuzzi yearlong
Outdoor pool, a heated pool

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
The price is HK$9,378
HK$14,792 total
includes taxes & fees
26 Jul - 27 Jul
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Private kitchen

Spacious house in East Hampton with heated pool + WFH

Spacious house in East Hampton with heated pool + WFH
East Hampton
The price is HK$5,646
HK$11,154 total
includes taxes & fees
3 Aug - 4 Aug
Spacious house in East Hampton with heated pool + WFH
Exterior

Sag Harbor Village Chic with water views

Sag Harbor Village Chic with water views
Sag Harbor
9.8 out of 10, Exceptional, (8 reviews)
"The lilacs were in bloom and we could walk to town for eggs and milk. A relaxing stay in a beautiful town."
United States
Claire W.
The price is HK$15,683
HK$24,413 total
includes taxes & fees
22 Aug - 23 Aug
Sag Harbor Village Chic with water views
Beach nearby, sun-loungers, beach towels

Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants

Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
Southampton
10.0 out of 10, Exceptional, (2 reviews)
"Had a great stay for a long weekend in the Hamptons. House was cozy and comfortable and in a good location."
United States
Beverly J.
The price is HK$5,086
HK$9,708 total
includes taxes & fees
26 Jul - 27 Jul
Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
Exterior

Unit 1311: Cottage | Garden View | Deuce

Unit 1311: Cottage | Garden View | Deuce
Napeague
8.0 out of 10, Very good, (2 reviews)
"Great location a few steps always from the ocean and a few minutes away from town"
United States
Jessica S.
The price is HK$7,269
HK$11,618 total
includes taxes & fees
26 Jul - 27 Jul
Unit 1311: Cottage | Garden View | Deuce
Terrace/patio

Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (17 reviews)
"Amazing views, beautiful property and pet friendly! Clean, well equipped."
United States
Ana B.
The price is HK$2,533
HK$11,473 total
includes taxes & fees
23 Jul - 24 Jul
Black Swan Beachfront Home with Jacuzzi year round
Terrace/patio

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is HK$3,207
HK$4,551 total
includes taxes & fees
26 Jul - 27 Jul
American Beech in Greenport - Petite King Room 7
Beach

Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (7 reviews)
"Everything was so nice and clean. Location was great, walking distance from everything. My children had an amazing time. I would book this again in the summer."
United States
Jessica0610@gmail.com A.
The price is HK$3,882
HK$6,352 total
includes taxes & fees
29 Jul - 30 Jul
Beach Block Hideaway
Living area

Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom
Southampton
10.0 out of 10, Exceptional, (4 reviews)
"Great location. Loved the yard but for small pets the fence has some areas they could get under but overall it worked out. Just kept an eye on them.House very clean, comfortable. Host communication was excellent and would highly recommend for a visit to Southampton. Easy walk into town."
United States
Kathy B.
The price is HK$7,057
HK$13,304 total
includes taxes & fees
2 Aug - 3 Aug
Minutes from the beach, brand new 3 bedroom
Sun-loungers, beach towels

The SandPiper

The SandPiper
Pipes Cove
9.8 out of 10, Exceptional, (43 reviews)
"Lovely place, very clean, host was very responsive. Thanks so much!"
United States
Marie H.
The price is HK$2,313
HK$4,049 total
includes taxes & fees
17 Aug - 18 Aug
The SandPiper
Coffee/tea maker, fridge, microwave, oven

Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is HK$4,313
HK$7,373 total
includes taxes & fees
26 Jul - 27 Jul
Immaculate Waterfront 2 bedroom!
Sun-loungers, beach towels

Aqua Vista

Aqua Vista
Pipes Cove
9.8 out of 10, Exceptional, (39 reviews)
"great anf friendly, clean"
United States
Sophia
Aqua Vista
Interior

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
Sag Harbor
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home !"
United States
Nadja B.
The price is HK$23,525
HK$34,277 total
includes taxes & fees
28 Jul - 29 Jul
Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
Outdoor dining

Hampton Bays Townhouse - Pool, Beach Access

Hampton Bays Townhouse - Pool, Beach Access
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
"This was the perfect spot for us for a quick weekend stay in Hampton Bays. Close to Ponquoge Beach, restaurants, stores, etc. Great size for our group of four. We didn’t get a chance to use the pool because we didn’t get the good weather, but we will be back. Good value for price. Irina was excellent at communicating. We loved our short stay here. Would highly recommend to my friends."
United States
Eileen O.
The price is HK$2,470
HK$5,061 total
includes taxes & fees
14 Aug - 15 Aug
Hampton Bays Townhouse - Pool, Beach Access
Outdoor dining

Villa Luz Family Home w/ heated pool & jacuzzi

Villa Luz Family Home w/ heated pool & jacuzzi
Hampon Bays
9.6 out of 10, Exceptional, (25 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is HK$1,702
HK$14,202 total
includes taxes & fees
26 Jul - 27 Jul
Villa Luz Family Home w/ heated pool & jacuzzi
Outdoor pool, a heated pool

Elegant 5-Bedroom Hamptons Home with Private Pool

Elegant 5-Bedroom Hamptons Home with Private Pool
Hampton Bays
9.4 out of 10, Exceptional, (36 reviews)
"My family and I really enjoyed this home. Everything you can think of is provided for you. We would definitely stay here again!"
United States
Sarah A.
The price is HK$7,998
HK$13,007 total
includes taxes & fees
20 Aug - 21 Aug
Elegant 5-Bedroom Hamptons Home with Private Pool
Interior

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

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is HK$21,525
HK$31,052 total
includes taxes & fees
31 Jul - 1 Aug
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wainscott Hotel Reviews

Montauk Blue Hotel

Montauk Blue Hotel

10/10 Excellent
"The location. The cleaning room was very nice"
Jose 2-night trip
Posted 1 day ago
Montauk Blue Hotel

Find out more about Wainscott

Wainscott Vacation Homes information

Number of reviews
1,853
Accommodation
1405 Vacation Homes
Lowest Price
HK$2,499
Highest Price
HK$14,063

Explore a world of travel with Expedia