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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)
"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, (131)
"Perfect property to hangout and stay entertained for hours"
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)
"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, (67)
"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, (50)
"Super responsive host. Stayed in the offseason so pool was closed but was super quiet and the ocean is so close. "
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 3,336 total
includes taxes & fees
29 Apr - 30 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

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, (1162)
"Above and beyond what we expected for an off-season stay! Beautifully maintained property, gorgeous view from our room's balcony, kind and helpful staff. Will definitely be back in the near future."
The price is AED 555
AED 706 total
includes taxes & fees
19 May - 20 May
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (371)
"Perfect for a quick getaway. The location can’t be beat. Loved the beach-themed decor also."
The price is AED 500
AED 611 total
includes taxes & fees
27 Apr - 28 Apr
Montauk Oceanside Suites

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (282)
"2nd loft bedroom/bath was especially nice"
The price is AED 524
AED 679 total
includes taxes & fees
27 Apr - 28 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.