Wainscott Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Tonight
Nov 30 - Dec 1
Tomorrow
Dec 1 - Dec 2
Next weekend
Dec 5 - Dec 7
In two weeks
Dec 12 - Dec 14

Vacation Rentals in Wainscott

5 bedrooms, desk, iron/ironing board, travel crib
Prime location! Walk to Beach! Wainscott Family House & Cottage. Pool & Hot Tub!

Vacation Home in Wainscott

9.8 out of 10, Exceptional, (29)
"The whole process was seamless. The owner was accessible and responsive. A tremendous property with a luxurious location. Highly recommend!!"
United States
Seth H.
Prime location! Walk to Beach! Wainscott Family House & Cottage. Pool & Hot Tub!
Front of property - evening/night
Montauk Manor

Aparthotel in Montauk

3.5 star property
9.2 out of 10, Wonderful, (1265)
"Always excellent, even suring my eleventh stay."
United States
Daryl
The price is ￥21,647
￥27,788 total
includes taxes & fees
Dec 2 - Dec 3
Montauk Manor
Beach nearby
Cliffside Resort Condominiums

Aparthotel in Greenport

3.0 star property
9.0 out of 10, Wonderful, (249)
"Great stay - beautiful place"
United States
Rebecca
Cliffside Resort Condominiums
Apartment | Private kitchen | Fridge, microwave, stovetop
Montauk Oceanside Suites

Aparthotel in Downtown Montauk

3.0 star property
8.6 out of 10, Excellent, (418)
"We loved it, suite size was great! "
United States
Patrick
Montauk Oceanside Suites
TV, fireplace, video library, stereo
Stunning Hampton Holiday Family Fantasy for your Team

Vacation Home in East Hampton

9.8 out of 10, Exceptional, (74)
"Outstanding house, beautifully maintained and well stocked, with great location."
United States
Jason C.
Stunning Hampton Holiday Family Fantasy for your Team
Outdoor pool, a heated pool
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Vacation Home in Sag Harbor

10.0 out of 10, Exceptional, (89)
"House that has everything you need for a wonderful getaway! Excellent communication with the property owner. Thank you Jay for everything and your hospitality! "
United States
Maria R.
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Outdoor pool, a heated pool
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Vacation Home in Southampton

9.8 out of 10, Exceptional, (32)
"This place was so nice and so close to so many fun places! "
United States
Daniella L.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Smart TV, fireplace, stereo
Mid-Century Home with Pool, Private Beach Access, and Long-Stay Summer Savings

Vacation Home in East Hampton

10.0 out of 10, Exceptional, (95)
"Awesome location. Very comfortable stay. Had everything we needed. Would definitely stay here again"
United States
Irish T.
Mid-Century Home with Pool, Private Beach Access, and Long-Stay Summer Savings
Fridge, microwave, oven, stovetop
STUNNING LUXURY HOME ~ PRIVATE POOL/HOT TUB ~ PERFECT HAMPTONS GETAWAY ~ MBH

Vacation Home in East Hampton

9.6 out of 10, Exceptional, (39)
"Beautiful house! Great area! Great host!"
United States
brooke v.
STUNNING LUXURY HOME ~ PRIVATE POOL/HOT TUB ~ PERFECT HAMPTONS GETAWAY ~ MBH
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils
Driftwood Resort

Condo in Montauk

3.5 star property
9.0 out of 10, Wonderful, (236)
"Great place to stay for small family "
United States
DongHo
Driftwood Resort
One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu
Offshore Residences

Condo in Downtown Montauk

4.5 star property
The price is ￥74,810
￥103,314 total
includes taxes & fees
Dec 2 - Dec 3
Offshore Residences
On the beach, sun loungers, beach towels
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

Vacation Home in Montauk

9.8 out of 10, Exceptional, (108)
"Home suited us perfectly for a 10-day vacation with family and friends. The back yard is absolutely fantastic and was perfect for summer grill-outs and pool days. The neighborhood is very quiet and location was spot-on just a 5 minute walk to the beach. Can’t say enough good things about Carter’s home - even better than the pictures!! "
United States
Katie M.
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
1 bedroom, WiFi, bed sheets
Unobstructed Ocean Views ! A Beautiful Montauk Getaway

Vacation Home in Montauk

10.0 out of 10, Exceptional, (61)
"Amazing stay…. Great host, excellent location and very clean!"
Australia
Amy W.
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
Outdoor pool, a heated pool
A Quiet Place in the Hamptons

Vacation Home in East Quogue

9.6 out of 10, Exceptional, (38)
"Fantastic house for the extended family ! We loved the pool , enjoyed bbq grilling and hanging out together! "
United States
Anonymous traveler
A Quiet Place in the Hamptons
Pool
10 Bedroom Hampton House with a regulation size Pickleball court

Vacation Home in Hampton Bays

10.0 out of 10, Exceptional, (32)
"Location of this property is impeccable."
United States
Stephen M.
10 Bedroom Hampton House with a regulation size Pickleball court
On the beach
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!

Condo in Montauk

9.8 out of 10, Exceptional, (98)
"Very Nice stay there for business would go back for pleasure"
United States
Joseph C.
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
Terrace/patio
Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Camping in East Hampton

8.6 out of 10, Excellent, (4)
"Had a nice peaceful evening eating our pizza and relaxing while watching the sunset. Nice way to celebrate our 30th, back to the woods❤️"
United States
Ellen
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
A heated pool
Brand New in the Heart of East Hampton Village with Pool

Vacation Home in East Hampton

10.0 out of 10, Exceptional, (33)
"Wonderful house in brand-new condition, fantastic location with shops, restaurants, grocery, train-stop in wallking distance, very responsive and caring owner.Highly recommended."
United States
Philipp H.
Brand New in the Heart of East Hampton Village with Pool
Beach nearby, sun loungers, beach towels
Newly Renovated Montauk Condo with Ocean Views!

Apartment in Montauk

9.8 out of 10, Exceptional, (84)
"We had a great time relaxing and taking quiet walks on the beach. The beach access was very close and very quiet. "
United States
Shawn B.
Newly Renovated Montauk Condo with Ocean Views!
Property grounds
Work and Play Special! Extended Stay Discount

Vacation Home in Shelter Island

10.0 out of 10, Exceptional, (53)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
Work and Play Special! Extended Stay Discount
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

The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"Great hotel for a quick stay - very friendly staff"
Dianne 1-night trip
Posted 6 days ago
The Atlantic Hotel

Find out more about Wainscott

Search for holiday rentals in Wainscott on Expedia! You can easily find your home rentals, villas, holiday apartments in Wainscott using one of the methods below:

  • View our selection of featured holiday rentals in Wainscott
  • Use the map to find apartments and other holiday homes in the Wainscott neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Wainscott while they last

Look no further and take a look at our great range of rental properties in Wainscott!

Frequently asked questions

Can I find vacation rentals in Wainscott?

Yes, we have vacation rentals near well known points of interest in Wainscott, or you can choose a secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Wainscott. Make sure you have time to check out the bars and coffeehouses during your trip.

What's the top vacation rental that Wainscott has to offer?

9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub: This vacation home rental near Wainscott is located by the ocean and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Wainscott?

Expedia has 38 vacation rentals for your stay in Wainscott.

What can I see and do in Wainscott?

Explore the area and family-friendly sights such as Railroad Museum of Long Island, or get out into nature at a spot like The Hamptons Beaches. In the larger area, you’ll find Georgica Beach and Wolffer Estates Vineyard.

What are vacation rentals like in Wainscott?

Vacation rentals are privately owned properties you can book for a short or long stay in Wainscott. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for small groups.