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Wainscott Holiday Rentals

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Our top choices for Wainscott holiday rentals

1. East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
10.0 out of 10, Exceptional, (2 reviews)
"We have just returned from an amazing summer experience in East Hampton! From the minute I secured the booking to checkout, everything was perfectly smooth! The house was so wonderful, every design detail and amenity…. It was truly like the best of all possible creature comforts…. Fully stocked kitchen, incredible fire pit for late evening s’mores, extraordinary huge pool, patio with outdoor speakers, and enough indoor space meticulously designed and decorated that proved our dream vacation...
United States
GINA W.
The price is NZ$2,202
includes taxes & fees
16 Sept - 17 Sept
East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace

2. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (1 review)
"We thoroughly enjoyed our stay. The property was exactly as described, very well maintained, comfortable, and welcoming. The location is ideal for exploring the Hamptons, with convenient access to Sag Harbor, East Hampton, and Bridgehampton. We would definitely recommend this property to others visiting the area."
United States
Robert R.
The price is NZ$950
includes taxes & fees
21 Sept - 22 Sept
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

3. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is NZ$865
includes taxes & fees
30 Sept - 1 Oct
Charming Accommodations in the Hamptons

4. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (322 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
The price is NZ$435
includes taxes & fees
9 Sept - 10 Sept
Windward Shores Ocean Resort

5. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (290 reviews)
"Great place!"
United States
Christine
The price is NZ$734
includes taxes & fees
21 Sept - 22 Sept
Cliffside Resort Condominiums

6. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (52 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is NZ$579
includes taxes & fees
15 Sept - 16 Sept
North Fork Resort

7. Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely Beautiful view The vibe and food was great. Just beware of the tics."
United States
Christina V.
The price is NZ$535
includes taxes & fees
9 Sept - 10 Sept
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

8. Beautiful East Hampton Retreat

Beautiful East Hampton Retreat
East Hampton
9.6 out of 10, Exceptional, (5 reviews)
"The host was very easy to work with. He was attentive and responsive. The home was exactly as advertised and was clean and nice to stay in!"
United States
Jonathan S.
The price is NZ$2,251
includes taxes & fees
2 Sept - 3 Sept
Beautiful East Hampton Retreat

9. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (248 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is NZ$378
includes taxes & fees
21 Sept - 22 Sept
Driftwood Resort

10. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

11. Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (4 reviews)
"great"
United States
Fiona B.
The price is NZ$519
includes taxes & fees
3 Sept - 4 Sept
Safari Tent Glamping,D27-CedarPt, East Hampton, NY

12. Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
6.0 out of 10, (1 review)
"For a last minute trip, we couldn't beat the location. Less than 10 minutes from Sag Harbor and Bridgehampton main streets as well as from Sagaponack beaches. The space is quaint and offers everything you need, a small kitchenette, a work desk, outdoor space. There was several communications sent regarding privacy and not interacting with other guests on property which I can appreciate but felt excessive.My two biggest complaints and likely why I would not rebook was first the cleanliness of the...
United States
Emily t.
The price is NZ$993
includes taxes & fees
30 Sept - 1 Oct
Lovely studio with AC in charming Sag Harbor

13. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,397 reviews)
"Beautiful property"
United States
John
The price is NZ$511
includes taxes & fees
10 Sept - 11 Sept
Montauk Manor

14. BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.2 out of 10, Wonderful, (7 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 NZ$2,767
includes taxes & fees
8 Sept - 9 Sept
BlackBerry Private home with jacuzzi yearlong

15. Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Southampton
9.6 out of 10, Exceptional, (10 reviews)
"great experience"
United States
Jordan
The price is NZ$950
includes taxes & fees
13 Sept - 14 Sept
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

16. Safari Tent Glamping,D29-CedarPt, East Hampton, NY

Safari Tent Glamping,D29-CedarPt, East Hampton, NY
East Hampton
8.0 out of 10, Very good, (1 review)
"If you upgrade the bathroom and shower facilities for glamping only- even if you increase the rate to stay- that would make it a true glamping experience. Willing to pay extra for better bathrooms and showers. Consider renting fancy bathroom and showers and increasing your prices. Thank you. Other than that it was wonderful."
United States
Aurelia
The price is NZ$518
includes taxes & fees
2 Sept - 3 Sept
Safari Tent Glamping,D29-CedarPt, East Hampton, NY

17. Spacious house in East Hampton with heated pool + WFH

Spacious house in East Hampton with heated pool + WFH
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Great clean beautiful property."
United States
ANGELA S.
The price is NZ$1,995
includes taxes & fees
30 Sept - 1 Oct
Spacious house in East Hampton with heated pool + WFH

18. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (57 reviews)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
The price is NZ$2,202
includes taxes & fees
10 Sept - 11 Sept
Work and Play Special! Extended Stay Discount

19. Unit 2024: 1-Bedroom with Loft | 2nd Floor-Bay View | Court Side

Unit 2024: 1-Bedroom with Loft | 2nd Floor-Bay View | Court Side
Napeague
Unit 2024: 1-Bedroom with Loft | 2nd Floor-Bay View | Court Side

20. Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
The price is NZ$497
includes taxes & fees
2 Sept - 3 Sept
Safari Tent Glamping,S4-CedarPt, East Hampton, NY
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 Hotel Reviews

Find out more about Wainscott

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Wainscott holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Wainscott. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Wainscott. Seeing all the best attractions is bound to make you fall in love with Wainscott. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Wainscott short-term rentals, that won’t be hard to do.

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?

The Hampton Sack a cheerful relaxing beach cottage: This holiday home rental outside of Wainscott is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Wainscott?

Expedia has 38 holiday rentals for your stay in Wainscott.

What can I see and do in Wainscott?

Explore the area and family-friendly sights such as Children's Museum of The East End, 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.