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Holiday Rentals in Wainscott Woods

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Holiday Rentals in Wainscott Woods

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1204)
"The property was gorgeous, and the staff were very friendly and eager to assist. Also, the restaurant was very good!"
The price is €465
includes taxes & fees
6 Jul - 7 Jul
Montauk Manor

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (286)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is €348
includes taxes & fees
9 Jul - 10 Jul
Windward Shores Ocean Resort

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (260)
"Quiet, relaxing place to stay, great access to the beach and town!"
The price is €372
includes taxes & fees
7 Jul - 8 Jul
The Surf Club

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (388)
"great place to stay"
The price is €256
includes taxes & fees
7 Jul - 8 Jul
Montauk Oceanside Suites

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (223)
"After some lengthy travel to get to LI this was an excellent choice to start our vacation. Great accommodations, comfortable and great location. "
The price is €557
includes taxes & fees
6 Jul - 7 Jul
Cliffside Resort Condominiums

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (224)
"The staff was very friendly I will definitely be back again 👍"
The price is €472
includes taxes & fees
13 Jul - 14 Jul
Driftwood Resort

Canoe Place Waterfront Residences

4.0 star property
The price is €2,047
includes taxes & fees
6 Jul - 7 Jul
Canoe Place Waterfront Residences

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (67)
"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"
Fairy Tale Guest Cottage in Magic Garden by Pool

Escape to Sag Harbor

10.0 out of 10, Exceptional, (47)
"Amazing house and location!! Would stay again "
Escape to Sag Harbor

Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

8.6 out of 10, Excellent, (25)
"This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!...
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

Perfect East Hampton Getaway!Pool, HotTub, PirateShip, Trampoline, Walk to Beach

10.0 out of 10, Exceptional, (85)
"Great time"
Perfect East Hampton Getaway!Pool, HotTub, PirateShip, Trampoline, Walk to Beach

East Hampton- Beautiful 4 Bedroom Home, Large Heated Pool, Private Backyard

10.0 out of 10, Exceptional, (75)
"Stayed here over Thanksgiving. Beautiful house, well appointed, great location. The Hamptons at Thanksgiving are very vibrant. Highly recommend a stay here. "
East Hampton- Beautiful 4 Bedroom Home, Large Heated Pool, Private Backyard

Charming East Hampton Home, private yard with fenced in pool, perfect for...

Charming East Hampton Home, private yard with fenced in pool, perfect for...

Lovely North Fork Beach Cottage (2 BR/2 bath)!

10.0 out of 10, Exceptional, (114)
"We were pleased with our stay. The house was very clean. My contact with the property manager were great. Would stay again."
Lovely North Fork Beach Cottage (2 BR/2 bath)!

Southampton cozy cottage by the beach

The price is €827
includes taxes & fees
27 Jul - 28 Jul
Southampton cozy cottage by the beach

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (87)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Retro Modern 3-Bedroom House with Heated Pool, Large Deck, WiFi in East Hampton

Retro Modern 3-Bedroom House with Heated Pool, Large Deck, WiFi in East Hampton

Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum

10.0 out of 10, Exceptional, (45)
"Great house, kitchen is well equipped which made dining in very easy. Loved the pool and backyard."
Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum

Newly Renovated Montauk Condo with Ocean Views!

9.8 out of 10, Exceptional, (82)
"Super clean, beautiful water views and great location. Would definitely recommend and would stay again."
Newly Renovated Montauk Condo with Ocean Views!

Stunning Southampton Village Modern Home

The price is €14,384
includes taxes & fees
4 Jul - 5 Jul
Stunning Southampton Village Modern Home
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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Frequently asked questions

Can I find a holiday rental in Wainscott Woods?

Yes, there are holiday rentals close to the most popular sights in Wainscott Woods, or you can select a more secluded option if you're looking for a relaxing stay.

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

Escape to Sag Harbor: This holiday home rental outside of Wainscott Woods offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a pool table so that you can immerse yourself in your holiday.

How many holiday rentals are there in Wainscott Woods?

With 19 Expedia holiday rentals, you're guaranteed 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 wider area.

What’s a holiday rental in Wainscott Woods like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Wainscott Woods. Holiday rentals offer amenities such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.