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Compare 1687 Vacation Homes in Wainscott with updated reviews, rates, and availability.

10 Bedroom Hampton House with a regulation size Pickleball

10.0 out of 10, Exceptional, (25)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

10.0 out of 10, Exceptional, (98)
"The house and stay were great!"
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

Stunning New Designer Renovation

9.4 out of 10, Exceptional, (21)
"We had a wonderful stay at this home! The yard is the most spectacular thing ever- pictures don't do it justice! And the location is wonderful. Great for our growing family :)"
Stunning New Designer Renovation

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (131)
"Wonderful throw back beach house..nothing fancy but very comfortable and the views are amazing! Loved spending our Christmas Holiday relaxing by the bay..and the year round hot tub was up and running when we got there! Perfect spot..will definitely go back next year! "
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

4-bedroom house is across the street from private beach and walk to town

2.0 star property
4-bedroom house is across the street from private beach and walk to town

Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

9.8 out of 10, Exceptional, (99)
"Had a great experience at this property!"
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

Secluded 1 Br Cottage on the Lake, Close to Ditch with OS Shower & Fabulous Yard

9.8 out of 10, Exceptional, (39)
"Perfect location for our stay. Very comfy and clean cottage. "
Secluded 1 Br Cottage on the Lake, Close to Ditch with OS Shower & Fabulous Yard

Charming Village home in the heart of Southampton

10.0 out of 10, Exceptional, (20)
"Great location, clean, easy checkin, slept 7 comfortably"
Charming Village home in the heart of Southampton

Cozy House less than two miles from Ocean Beaches

10.0 out of 10, Exceptional, (5)
"The house is very nice and cozy. It was nice get away from NYC."
Cozy House less than two miles from Ocean Beaches

Montauk Cozy Beach Studio. Walk to private ocean beach & always pet friendly!

10.0 out of 10, Exceptional, (2)
"The host is the sweetest person. Place was comfy and just what we needed for a lovely getaway in montauk. Can’t wait to come back"
Montauk Cozy Beach Studio. Walk to private ocean beach & always pet friendly!

Stunning Hampton Holiday Family Fantasy for your Team

9.8 out of 10, Exceptional, (67)
"Everything was great!!!"
Stunning Hampton Holiday Family Fantasy for your Team

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.0 out of 10, Exceptional, (19)
"Had the best girls weekend with old college roommates! The house is stunning and incredibly clean. Was well stocked with everything we needed for our stay. Great location as well for checking out downtown, the beach, wineries, etc. "
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Unobstructed Ocean Views ! A Beautiful Montauk Getaway

10.0 out of 10, Exceptional, (50)
"Great location, great stay! "
Unobstructed Ocean Views ! A Beautiful Montauk Getaway

MONTAUK Beach House with pool… Perfect for Families & Friends

9.8 out of 10, Exceptional, (25)
"Really enjoyed staying here. Cannot recommend enough!"
MONTAUK Beach House with pool… Perfect for Families & Friends

Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

2.0 star property
7.4 out of 10, Good, (3)
"I had so much fun with my friends"
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

Magic Place

The price is AED 1,653
AED 3,357 total
includes taxes & fees
1 May - 2 May
Magic Place

Charming and Spacious Wainscott Home close to Town and Beaches, Great for...

10.0 out of 10, Exceptional, (1)
"This home is lovely and sleek with all new features and amenities. Beds were extremely comfortable and grand."
Charming and Spacious Wainscott Home close to Town and Beaches, Great for...

Watermill Retreat, minutes from Southampton Town Ctr and Beaches!

9.6 out of 10, Exceptional, (12)
"Wonderful stay for an amazing price! A nice compact/easy house with a family friendly backyard. Great neighborhood!"
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!

North Fork Family and Friends Getaway. Great Location

10.0 out of 10, Exceptional, (9)
"We had a great stay! The house had everything we needed and was in a wonderful location to explore the North Fork. Barbara was incredibly gracious - very responsive and helpful. We hope to make a return visit!"
North Fork Family and Friends Getaway. Great Location

COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach

10.0 out of 10, Exceptional, (13)
"Steps to probably the most beautiful beach in the Hamptons. Thoroughly enjoyed our stay, as did the dogs. We will definitely be back."
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach
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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Other property types in Wainscott

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1165)
"excellent overall stay"
The price is AED 555
AED 706 total
includes taxes & fees
13 May - 14 May
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (374)
"Good for a short stay "
The price is AED 562
AED 682 total
includes taxes & fees
1 May - 2 May
Montauk Oceanside Suites

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (283)
"Love the ocean view from the balcony"
The price is AED 524
AED 679 total
includes taxes & fees
1 May - 2 May
Windward Shores Ocean Resort
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.