Brioche buns with chocolate chips priced at $3.50.

Wainscott Woods Holiday Rentals

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Our top choices for Wainscott Woods holiday rentals

1. 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 AU$802
includes taxes & fees
21 Sept - 22 Sept
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

2. 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 AU$590
includes taxes & fees
27 Sept - 28 Sept
Cliffside Resort Condominiums

3. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is AU$738
includes taxes & fees
15 Sept - 16 Sept
Charming Accommodations in the Hamptons

4. 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 AU$484
includes taxes & fees
7 Sept - 8 Sept
North Fork Resort

5. 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 AU$286
includes taxes & fees
4 Oct - 5 Oct
Windward Shores Ocean Resort

6. 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 AU$312
includes taxes & fees
28 Sept - 29 Sept
Driftwood 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 AU$452
includes taxes & fees
7 Sept - 8 Sept
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

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

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
The price is AU$452
includes taxes & fees
7 Sept - 8 Sept
Safari Tent Glamping,S4-CedarPt, East Hampton, NY

9. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,398 reviews)
"Beautiful property"
United States
John
The price is AU$422
includes taxes & fees
10 Sept - 11 Sept
Montauk Manor

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.
The price is AU$1,701
includes taxes & fees
7 Sept - 8 Sept
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

11. 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 AU$821
includes taxes & fees
7 Sept - 8 Sept
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

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 AU$846
includes taxes & fees
15 Sept - 16 Sept
Lovely studio with AC in charming Sag Harbor

13. Designer East Hampton Farmhouse - Bike to Amagansett, EH & Ocean Beaches, Pool

Designer East Hampton Farmhouse - Bike to Amagansett, EH & Ocean Beaches, Pool
East Hampton North
Designer East Hampton Farmhouse - Bike to Amagansett, EH & Ocean Beaches, Pool

14. 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.
Beautiful East Hampton Retreat

15. 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 AU$2,357
includes taxes & fees
8 Sept - 9 Sept
BlackBerry Private home with jacuzzi yearlong

16. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (448 reviews)
"It was wonderful"
United States
christopher
The price is AU$241
includes taxes & fees
28 Sept - 29 Sept
Montauk Oceanside Suites

17. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is AU$569
includes taxes & fees
15 Sept - 16 Sept
Beach Block Hideaway

18. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (23 reviews)
"Close to the train, beach and restaurant, very convenient on foot"
United States
Nigel
The price is AU$489
includes taxes & fees
13 Sept - 14 Sept
Harbor Heights

19. Safari Tent Glamping,D28-CedarPt, East Hampton, NY

Safari Tent Glamping,D28-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (5 reviews)
"It was a really great experience! We barbecued and made a camp fire. Took a walk on the beach. Played in the playground. The pizza and breakfast sandwiches in the café were delicious! We will definitely be coming back!"
United States
Brian F.
The price is AU$466
includes taxes & fees
7 Sept - 8 Sept
Safari Tent Glamping,D28-CedarPt, East Hampton, NY

20. 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 AU$466
includes taxes & fees
7 Sept - 8 Sept
Safari Tent Glamping,D27-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 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$241 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.

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

The Hampton Sack a cheerful relaxing beach cottage: This holiday home rental outside of Wainscott Woods 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 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 Children's Museum of The East End, 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.