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Compare 1697 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)
"Pam was very communicative prior to our stay and a welcoming host. The house was clean, centrally located, and spacious. "
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, (129)
"We came to enjoy a nice relaxing weekend with friends and were overwhelmed with how amazing the beach house was! Completely set in the perfect spot! We loved the space and all the games! Thank you for creating such a fun home! We will be back "
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

Sprawling Southampton Home: Private Pool

9.0 out of 10, Wonderful, (44)
"My family and I had a wonderful stay at this property. The house was well-situated in a quiet neighborhood - very private, surrounded by trees and a few wild turkeys. There were many amenities that made our stay enjoyable from the large patio and pool, 3 full baths in the main house, one of which had an amazing shower system with body spray, and a designated work area for those that can’t leave work behind. Communication with the property manager was easy and Debbie was very helpful and...
Sprawling Southampton Home: Private Pool

Charming Village home in the heart of Southampton

10.0 out of 10, Exceptional, (20)
"We loved our stay! The location was perfect for our family, so easy to walk to town, close to the beach and easy to get to other towns. House was perfect as well, we didn’t get to enjoy the outdoors due to rain but loved the indoor space. Plenty of places to hang and enjoy/relax. Hoping to visit again soo!"
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 was everything we needed for a weekend away! The house was very clean and cute esthetics. The back yard was great for the dogs. Claudea gave us great recommendations for places to eat. We would def rebook this house! "
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)
"Lovely to be away in a spot just hidden enough to be accessible from the main road but not close to it. Near to the beach but not on top of it. Perfect! Quiet, woody, peaceful, restful and pet friendly. A hidden gem. The only thing I regret is not having time to stay longer."
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, (66)
"Great home"
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)
"Perfect spot for a girls weekend! Property/house as advertised, and the house was fully stocked with all amenities. Thanks for a wonderful stay!! "
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Unobstructed Ocean Views ! A Beautiful Montauk Getaway

10.0 out of 10, Exceptional, (47)
"We thoroughly enjoyed staying here, short walk to town, beautiful scenery, quiet and clean. "
Unobstructed Ocean Views ! A Beautiful Montauk Getaway

MONTAUK Beach House with pool… Perfect for Families & Friends

9.8 out of 10, Exceptional, (25)
"Charlie is very responsive and the property is beautiful."
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 2,920 total
includes taxes & fees
31 Mar - 1 Apr
Magic Place

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

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)
"We loved this house and Margaux was a great host! Communication was easy and excellent. We loved every minute! Thanks!"
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!

North Fork Family and Friends Getaway. Great Location

10.0 out of 10, Exceptional, (9)
"10 of us stayed at this house during LDW and had the most incredible experience. The pictures do not do the house justice- it was even better than we anticipated. Beyond gorgeous, so clean, huge, and the backyard will leave you speechless. We cannot recommend it enough. The only downside was the bedrooms upstairs were warm. Thank you to our amazing hosts!!!! We will be back. "
North Fork Family and Friends Getaway. Great Location
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, (1147)
"Old architecture, modern amenities, great little town "
The price is AED 525
AED 671 total
includes taxes & fees
31 Mar - 1 Apr
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (367)
"Had a great stay here . Staff was friendly and check in and out was a breeze . Was very clean and comfortable. Only complaint was I couldn’t get a hot shower . Otherwise place is excellent. Shops , restaurants and bars are all a short walk . "
The price is AED 500
AED 611 total
includes taxes & fees
31 Mar - 1 Apr
Montauk Oceanside Suites

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (275)
"Great cozy place"
The price is AED 484
AED 633 total
includes taxes & fees
1 Apr - 2 Apr
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.