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Wainscott Woods Holiday Rentals

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Holiday Rentals in Wainscott Woods

Montauk Manor

3.5 star property
Montauk
9.2 out of 10, Wonderful, (1262)
"Always excellent, even suring my eleventh stay."
United States
Daryl
The price is AU$273
includes taxes & fees
1 Dec - 2 Dec
Montauk Manor

Montauk Oceanside Suites

3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (417)
"We loved it, suite size was great! "
United States
Patrick
Montauk Oceanside Suites

Cliffside Resort Condominiums

3.0 star property
Greenport
9.0 out of 10, Wonderful, (248)
"Great stay - beautiful place"
United States
Rebecca
Cliffside Resort Condominiums

Stunning Hampton Holiday Family Fantasy for your Team

East Hampton
9.8 out of 10, Exceptional, (74)
"We had an incredible stay! The property was as advertised. Very easy in and out and stocked with all the essentials to cook, hangout, use the pool or have a movie night. Our host was very responsive throughout the weekend and gave great recommendations. Highly recommend. "
United States
Henry S.
Stunning Hampton Holiday Family Fantasy for your Team

Driftwood Resort

3.5 star property
Montauk
9.0 out of 10, Wonderful, (236)
"Great place to stay for small family "
United States
DongHo
Driftwood Resort

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

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

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

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

Offshore Residences

4.5 star property
Downtown Montauk
The price is AU$994
includes taxes & fees
20 Nov - 21 Nov
Offshore Residences

Unobstructed Ocean Views ! A Beautiful Montauk Getaway

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

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Hampton Bays
9.4 out of 10, Exceptional, (75)
"Great Hamptons break with family. We had an amazing time with great pool, tennis, firepit and beautiful house. Very relaxing and close to fantastic beaches and nice ice cream spots and beach bars."
United Kingdom
Jack T.
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Mid-Century Home with Pool, Private Beach Access, and Long-Stay Summer Savings

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

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Hampton Bays
9.6 out of 10, Exceptional, (143)
"Large house and deck with plenty of room Beautiful view of bay Not easy to get from deck to water because of boulders "
United States
Robert H.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

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

A Quiet Place in the Hamptons

East Quogue
9.6 out of 10, Exceptional, (38)
"The property was exactly as advertised and Mateo was extremely responsive and went above and beyond. The bedrooms were very large and the common areas easily accommodated our large group. We had a wonderful time and would visit here again. "
United States
Judy D.
A Quiet Place in the Hamptons

Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

Jamesport
10.0 out of 10, Exceptional, (8)
"The is great!!! Very convenient location and plenty to do."
United States
Jose G.
Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!

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!

MONTAUK MANOR-DELUXE STUDIO APARTMENT

MONTAUK
9.8 out of 10, Exceptional, (76)
"Our stay was excellent however the bed in our room was as firm as bricks, needed to use the mattress from the pull out couch to put on top of the bed, tried to sleep on the pull out first but you can feel the springs."
United States
Dietmar S.
MONTAUK MANOR-DELUXE STUDIO APARTMENT

Newly Renovated Montauk Condo with Ocean Views!

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!

Safari Tent Glamping,S5-CedarPt, East Hampton, NY

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

Brand New in the Heart of East Hampton Village with Pool

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
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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Top Wainscott Woods Hotel Reviews

Find out more about Wainscott Woods

Everything you need to know about Wainscott Woods 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 Woods 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 Woods holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Wainscott Woods holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wainscott Woods. 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 Woods 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 Woods holiday rentals we have selected for you start as low as AU$273 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Wainscott Woods rentals

At Expedia, we put the best Wainscott Woods 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 Woods 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 Woods 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 Woods. 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 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.

How many holiday rentals are there in Wainscott Woods?

With 18 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.