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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

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

10 Bedroom Hampton House with a regulation size Pickleball
Pool

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 🏖
Outdoor dining

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
View from property

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!
Terrace/patio

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
Terrace/patio

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
On the beach, sun loungers, beach towels

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
On the beach

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
Smart TV

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
Sun loungers

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
Stunning Hampton Holiday Family Fantasy for your Team
TV, fireplace, video library, stereo

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
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (21)
"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
1 bedroom, WiFi, bed sheets

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

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
Smart TV, video games

Magic Place

The price is AED 1,653
AED 3,357 total
includes taxes & fees
12 May - 13 May
Magic Place
Charming and Spacious Wainscott Home close to Town and Beaches, Great for...
A heated pool

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!
Terrace/patio

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
Outdoor pool, a heated pool

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
Property grounds

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
Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10
Sun loungers, beach towels

Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10

10.0 out of 10, Exceptional, (5)
"We thoroughly enjoyed the home, and Carter was extremely helpful throughout our stay. The private parking access to the beach was awesome!"
Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10
Montauk Beach & Woods...Minutes to the beach, backyard woods!
Interior

Montauk Beach & Woods...Minutes to the beach, backyard woods!

10.0 out of 10, Exceptional, (7)
"Beautiful quiet family getaway with peek views of the ocean! Incredibly responsive owner who was concerned about our needs. Would highly recommend!"
Montauk Beach & Woods...Minutes to the beach, backyard woods!
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
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1179)
"excellent overall stay"
The price is AED 555
AED 706 total
includes taxes & fees
21 May - 22 May
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (374)
"Good for a short stay "
The price is AED 604
AED 730 total
includes taxes & fees
11 May - 12 May
Montauk Oceanside Suites
The Surf Club
On the beach, white sand

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (251)
"On the beach Heated pool Great facilities"
The price is AED 744
AED 1,050 total
includes taxes & fees
21 May - 22 May
The Surf Club
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.