Photo by Miriam Marcus

Wainscott Woods Holiday Rentals

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Holiday Rentals in Wainscott Woods

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1115)
"Nice, pleasant, staff was warm and friendly "
The price is AU$266
includes taxes & fees
24 Feb - 25 Feb
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very good, (362)
"I didn’t realize the property was mobile check-in and that all communication would be automated in the winter season. if you guys had that more clear on the Expedia it would be awesome. Otherwise the stay was great, clean room, no hassle to get in, right by the beach. "
The price is AU$218
includes taxes & fees
27 Feb - 28 Feb
Montauk Oceanside Suites

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (271)
"Beautiful location, clean property, and nice staff. Just hard to turn in to the parking lot but not much that the hotel can do for that. The private beach is stunning. "
The price is AU$271
includes taxes & fees
20 Mar - 21 Mar
Windward Shores Ocean Resort

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (251)
"The pictures of the property showed the bed in the bedroom facing the window with direct ocean views I was dis appointed to find out the bed was moved and no longer faced the ocean view."
The Surf Club

Stunning Hampton Holiday Family Fantasy for your Team

9.8 out of 10, Exceptional, (66)
"Great home"
Stunning Hampton Holiday Family Fantasy for your Team

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

9.8 out of 10, Exceptional, (98)
"Had a great experience at this property!"
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

10 Bedroom Hampton House with a regulation size Pickleball

10.0 out of 10, Exceptional, (25)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball

Newly Renovated Montauk Condo with Ocean Views!

9.8 out of 10, Exceptional, (75)
"Montauk has been our Happy Place for many years. We feel fortunate to have discovered this charming condo. Comfortable-feels like home. Immaculate. Consideration went into the details. Luxurious towels. Fantastic location near beach. And owner is a pleasure, right on top of communication. This place made our visit even Happier. Highly recommend. Thank You! Lynn"
Newly Renovated Montauk Condo with Ocean Views!

Montauk Cozy Beach Studio. Walk to private ocean beach & always pet friendly!

10.0 out of 10, Exceptional, (2)
"Lovely to be away in a spot just hidden enough to be accessible from the main road but not close to it. Near to the beach but not on top of it. Perfect! Quiet, woody, peaceful, restful and pet friendly. A hidden gem. The only thing I regret is not having time to stay longer."
Montauk Cozy Beach Studio. Walk to private ocean beach & always pet friendly!

Montauk Mansion INDOOR + OUTDOOR POOLS

9.6 out of 10, Exceptional, (88)
"Well kept unit. Easy access. Very quiet. Pool and spa area beautiful "
Montauk Mansion INDOOR + OUTDOOR POOLS

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (214)
"We were visiting our so. And just needed an inexpensive..relatively..place to stay….. this was quite convenient…. We had a good night sleep…took a walk to beach..had a great chat with one of the ‘beach boys’ and thought it was lovely……"
Driftwood Resort

Summer 2025 Now Available! Wolffer Vineyard Close!

10.0 out of 10, Exceptional, (83)
"Our stay was amazing! The house was fabulous, beautifully appointed, very clean, private and secluded. Lots to do in the area. Jay was very responsive and helpful when we had questions. Would definitely stay again. "
Summer 2025 Now Available! Wolffer Vineyard Close!

Classic East Hampton 5 BR in Private Beach Community.Pool, HotTub & Pirate Ship

10.0 out of 10, Exceptional, (80)
"The property was exactly as explained and all in our group loved the place. The house was clean and spacious with plenty of space to rekax."
Classic East Hampton 5 BR in Private Beach Community.Pool, HotTub & Pirate Ship

Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10

10.0 out of 10, Exceptional, (5)
"Our stay at Carters home was nothing short of perfect! Every day we walked to the beach, explored the charming town, grabbed coffee at Hampton Coffee, and enjoyed incredible restaurants nearby. Coming back to such a beautiful and comfortable house felt like a dream. We loved starting our mornings on the patio and cooling off in the pool and eating outside on the big table surrounded by lush flowers—absolute bliss! Highly recommend!""
Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10

Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound

9.4 out of 10, Exceptional, (31)
"A great corner condo in the Montauk Manor. Had a wonderful weekend. The condo was clean, and a great size for 3 adults. Got to use all the facilities at the manor. Indoor pool beautiful, sauna. Great restaurant and free shuttle bus to take you to town. Just a great weekend. "
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound

Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

2.0 star property
7.4 out of 10, Good, (3)
"I had so much fun with my friends"
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

Unobstructed Ocean Views ! A Beautiful Montauk Getaway

10.0 out of 10, Exceptional, (47)
"We thoroughly enjoyed staying here, short walk to town, beautiful scenery, quiet and clean. "
Unobstructed Ocean Views ! A Beautiful Montauk Getaway

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

9.6 out of 10, Exceptional, (127)
"Wonderful throw back beach house..nothing fancy but very comfortable and the views are amazing! Loved spending our Christmas Holiday relaxing by the bay..and the year round hot tub was up and running when we got there! Perfect spot..will definitely go back next year! "
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

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

10.0 out of 10, Exceptional, (18)
"My friends and I stayed at this house for a few days around New Year's. The house is very spacious, and the grounds are lovely. We had a group of 5 and had lots of room to congregate and disappear if we needed alone time. The hot tub was exactly what some of us needed, while the kitchen provided others with much comfort. The one bummer was when we arrived; it looked like someone had just had a party outside so that first made for a bit of cleanup. That little bump shouldn't stop you from...
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!

9.8 out of 10, Exceptional, (17)
"The house was clean and the location was magnificent. Jake was great, offered us early check in and late check out. The neighborhood was lovely, walked my pup and admired all of the beautiful homes. Definitely will stay there again. "
Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!
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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Other types of properties in Wainscott Woods you may be interested in

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1115)
"Nice, pleasant, staff was warm and friendly "
The price is AU$266
includes taxes & fees
24 Feb - 25 Feb
Montauk Manor

Gurney's Montauk Resort & Seawater Spa

4.0 star property
8.2 out of 10, Very good, (610)
"Beautiful views. Great staff and amenities."
The price is AU$817
includes taxes & fees
17 Mar - 18 Mar
Gurney's Montauk Resort & Seawater Spa

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very good, (362)
"I didn’t realize the property was mobile check-in and that all communication would be automated in the winter season. if you guys had that more clear on the Expedia it would be awesome. Otherwise the stay was great, clean room, no hassle to get in, right by the beach. "
The price is AU$218
includes taxes & fees
27 Feb - 28 Feb
Montauk Oceanside Suites
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.

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?

Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10: 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 balcony, a garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Wainscott Woods?

With 21 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.