Photo by Miriam Marcus

Wainscott Holiday Rentals

Save an average of 15% on thousands of properties with Expedia Rewards

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide

Find properties with these dates

Holiday Rentals in Wainscott

Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (70)
"Ricks home is STUNNING and very thoughtfully decorated. He was responsive and flexible. Thank you for an amazing stay!"
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
MONTAUK MANOR-DELUXE STUDIO APARTMENT
10.0 out of 10, Exceptional, (54)
"Studio was perfect and grounds of property were breaking. Would definitely stay there again. Got to enjoy Montauk and have a beautiful place to stay."
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, (27)
"Just had a great stay at this home. Pictures are extremely accurate and this home is so comfortable, clean and well equipped. Location is excellent. Close to town, hiking, beaches, vineyards. It really has it all! Host was wonderful and responsive. Would love book another stay."
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Save an average of 15% on thousands of hotels when you're signed in
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, (82)
"Great property in a great location"
The price is AU$1,474
includes taxes & fees
6 May - 7 May
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Recently renovated private 2.1 acre gated home with heated pool and tennis court
10.0 out of 10, Exceptional, (11)
"This beautiful home was a great vacation home for our entire family! The house was impeccably clean with a ton of amenities, everything we wanted or needed was provided. The basketball/tennis court provided hours of entertainment for our family and the swimming pool made for a great leisurely morning or afternoon of swimming and relaxing poolside. Julie was a very attentive host and responded to our text messages for suggestions on Gurney's Seawater Spa, Vegan restaurants and more. We had a...
Recently renovated private 2.1 acre gated home with heated pool and tennis court
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
9.8 out of 10, Exceptional, (89)
"We unfortunately had bad weather during our stay but we were cozy in this home which is spacious and conveniently located. For those with kids, there are safety gates and toys available. There’s a lot of outdoor seating and in the summer we look forward to returning to take advantage of the pool. Carter is very responsive - a terrific host!"
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Montauk Mansion With Outdoor Pool
9.8 out of 10, Exceptional, (78)
"We had a wonderful week and enjoyed being in this beautiful manor immensely. We strolled the grounds and caught gorgeous sunsets. The shuttle into downtown Montauk (5 mins away) allowed us to untether from our car and parking worries, and to spend time at the ocean and wandering the quaint downtown. It was the perfect spot and we would go back again."
Montauk Mansion With Outdoor Pool
Newly Renovated Montauk Condo with Ocean Views!
9.6 out of 10, Exceptional, (58)
"This condo unit was so nice. As a previous review noted, you can hear the ocean from inside, as well as see it for yourself from the lovely spacious deck. The bed was so comfortable, so much so that it stands out from most rentals. Remodeled shower was lovely, everything was simply decorated, and the place has pretty much anything you’d need. Kelly was very communicative and available when we had questions. A few mins drive from town or a 20ish minute walk. Would stay again!"
Newly Renovated Montauk Condo with Ocean Views!
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.4 out of 10, Exceptional, (27)
"Rainy but good weekend"
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1014)
"Loved the ambience and cleanliness and customer service. Monte’s restaurant was great and everything was nearby."
The price is AU$320
includes taxes & fees
8 May - 9 May
Montauk Manor
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (11)
"Since I stay for 2 days only it was fine. Check the shades , toilet paper and more towels. "
Location and views! Located directly on Shinnecock Bay!
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (179)
"Always a very nice time staying at this property. The sunset on the beach was amazing. Convenient to all area restaurants, wineries, breweries and Matchbook Distilling. "
The price is AU$490
includes taxes & fees
6 May - 7 May
Cliffside Resort Condominiums
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (233)
"Everything was just as described!"
The price is AU$298
includes taxes & fees
6 May - 7 May
Windward Shores Ocean Resort
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (180)
"Literally 1 minute walk to the sands. Clean and friendly environment. Would definitely coming back for short getaways. "
The price is AU$289
includes taxes & fees
7 May - 8 May
Driftwood Resort
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (218)
"Very nice location and nice condo"
The price is AU$447
includes taxes & fees
6 May - 7 May
The Surf Club
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, (292)
"Only wish it was more affordable in the summer to take my family. Besides that, clean, confortable, very pleasant."
The price is AU$258
includes taxes & fees
22 May - 23 May
Montauk Oceanside Suites
Beautiful 3 bedroom Residence in the Hamptons
Beautiful 3 bedroom Residence in the Hamptons
Don't see what you're looking for?
See all available properties in Wainscott
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.

Other types of properties in Wainscott you may be interested in

Sag Harbor Inn
3.5 star property
9.4 out of 10, Exceptional, (414)
"Very nice "
The price is AU$404
includes taxes & fees
8 May - 9 May
Sag Harbor Inn
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1014)
"Loved the ambience and cleanliness and customer service. Monte’s restaurant was great and everything was nearby."
The price is AU$320
includes taxes & fees
8 May - 9 May
Montauk Manor
The Wainscott Inn
3.0 star property
8.6 out of 10, Excellent, (91)
"Looks like the were in the process of updating? Lots of construction people and debris but we also went during off season so it made sense. Have to drive everywhere but still convenient!! "
The price is AU$355
includes taxes & fees
6 May - 7 May
The Wainscott Inn
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.

Everything you need to know about Wainscott holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wainscott holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wainscott holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Wainscott holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wainscott. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wainscott holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wainscott holiday rentals we have selected for you start as low as AU$243 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Wainscott rentals

At Expedia, we put the best Wainscott holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Wainscott rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wainscott holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wainscott. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Wainscott?

Yes, there are holiday rentals close to the most popular sights in Wainscott, or you can select a more 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 coffee shops during your trip.

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

Montauk Cozy Beach Studio. Walk to private ocean beach & always pet friendly!: This holiday home rental outside of Wainscott offers 1 hot tub, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Wainscott?

Expedia has 34 holiday 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 wider area, you’ll find Georgica Beach and Wolffer Estates Vineyard.

What are holiday rentals like in Wainscott?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Wainscott. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a family getaway.

Recent reviews of Wainscott properties
Expedia verified reviews