Wainscott Woods Vacation Rentals

  • 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

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Wainscott Woods vacation rentals

Living area

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is ￥237,949
￥310,616 total
includes taxes & fees
Apr 15 - Apr 16
Cozy 5 Bedroom With Wi-fi And Air Condition
Cottage, 2 Bedrooms, Patio | Free WiFi, bed sheets

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is ￥29,643
￥33,865 total
includes taxes & fees
Apr 20 - Apr 21
North Fork Cottages & RV Resort
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,324 reviews)
"Great property "
United States
brian
The price is ￥21,419
￥27,591 total
includes taxes & fees
Apr 15 - Apr 16
Montauk Manor
Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (249 reviews)
"Great stay - beautiful place"
United States
Rebecca
The price is ￥27,594
￥38,446 total
includes taxes & fees
Apr 15 - Apr 16
Cliffside Resort Condominiums
Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (310 reviews)
"Amazing stay! Place was perfect and staff was so friendly."
United States
Heather
The price is ￥23,609
￥31,305 total
includes taxes & fees
Apr 27 - Apr 28
Windward Shores Ocean Resort
Smart TV

Seabreeze 3 Cozy cottage by the beach

Seabreeze 3 Cozy cottage by the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is ￥16,564
￥77,615 total
includes taxes & fees
Apr 27 - Apr 28
Seabreeze 3 Cozy cottage by the beach
Terrace/patio

Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (16 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is ￥66,734
￥194,758 total
includes taxes & fees
Apr 22 - Apr 23
Black Swan Beachfront Home with Jacuzzi year round
Terrace/patio

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.2 out of 10, Wonderful, (5 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is ￥26,917
￥42,401 total
includes taxes & fees
Apr 15 - Apr 16
American Beech in Greenport - Petite King Room 7
Dining

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is ￥21,024
￥116,626 total
includes taxes & fees
Apr 19 - Apr 20
BlackBerry Private home with jacuzzi yearlong
Apartment | Living area

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (280 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is ￥26,714
￥39,188 total
includes taxes & fees
May 11 - May 12
The Surf Club
Apartment | Individually decorated, individually furnished, free WiFi, bed sheets

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (236 reviews)
"Great place to stay for small family "
United States
DongHo
The price is ￥26,608
￥35,591 total
includes taxes & fees
Apr 26 - Apr 27
Driftwood Resort
Apartment | Iron/ironing board, free WiFi

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (422 reviews)
"Great spot- walkable and nice accommodations! "
United States
Lesley
The price is ￥21,673
￥26,493 total
includes taxes & fees
Apr 28 - Apr 29
Montauk Oceanside Suites
Smart TV, fireplace

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (10 reviews)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
The price is ￥48,737
￥101,172 total
includes taxes & fees
Apr 15 - Apr 16
Renovated Townhouse walk to all
Dining

Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (5 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is ￥42,286
￥92,711 total
includes taxes & fees
Apr 15 - Apr 16
Northfork Townhouse walk to all
Interior

Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.2 out of 10, Wonderful, (5 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is ￥111,489
￥145,576 total
includes taxes & fees
Apr 15 - Apr 16
Cozy Hamptons Escape 3BR Minutes From Beach!
Interior

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is ￥159,211
￥268,204 total
includes taxes & fees
May 1 - May 2
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Property grounds

Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (11 reviews)
"Super location - just near The beautiful village of Greenport with a sweeping view of the bay, A very happy house - super Clean, and we had everything that we needed. Meghan was a wonderful host, and answered us quickly with any question that we had. I loved the NorthFork and this home was the perfect place to stay!"
United States
Carine J.
The price is ￥85,343
￥155,043 total
includes taxes & fees
Apr 15 - Apr 16
Beachfront Greenport Villa
Fridge, microwave, oven, stovetop

Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (53 reviews)
"This place is a perfect oasis in an already special environment. The host was wonderful and thoughtful. The cottage was magical and had everything to offer that one could want. "
United States
Adam M.
The price is ￥114,674
￥211,991 total
includes taxes & fees
Apr 15 - Apr 16
Work and Play Special! Extended Stay Discount
Smart TV, fireplace, stereo

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (4 reviews)
"perfect for families"
United States
Okito H.
The price is ￥107,507
￥223,454 total
includes taxes & fees
Apr 15 - Apr 16
Minutes from the beach, brand new 4 bedroom
One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (1 review)
The price is ￥87,439
￥118,097 total
includes taxes & fees
Apr 27 - Apr 28
Offshore Residences
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 Woods Hotel Reviews

The Shoals Suites and Slips

The Shoals Suites and Slips

10/10 Excellent
"The room was spacious. I’m very clean. I was very impressed. Location easy to get in and out of highly recommend."
Vivien 1-night trip
Posted 6 hours ago
The Shoals Suites and Slips

Find out more about Wainscott Woods

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

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

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

Frequently asked questions

Can I find a vacation rental in Wainscott Woods?

Yes, we have vacation rentals near the most popular attractions in Wainscott Woods, or you can go with a secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals that Wainscott Woods has to offer?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This vacation home rental near Wainscott Woods is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

How many vacation rentals are there in Wainscott Woods?

With 21 Expedia vacation rentals, you're sure to find just the right place for your Wainscott Woods stay.

What’s there to see and do in Wainscott Woods?

Explore the area and family-friendly sights such as Railroad Museum of Long Island, or get out into nature at a spot like Georgica Beach. Wolffer Estates Vineyard and The Jewish Center of the Hamptons are a couple of places you'll find in the larger area.

What’s a vacation rental in Wainscott Woods like?

A vacation rental is a private property you can stay in for a couple of days or more in Wainscott Woods. Vacation rentals feature extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.