Brioche buns with chocolate chips priced at $3.50.

Wainscott Woods Vacation Rentals

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Our top choices for Wainscott Woods vacation 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 CA $395
CA $810 total
includes taxes & fees
Sep 21 - Sep 22
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 CA $404
CA $585 total
includes taxes & fees
Sep 27 - Sep 28
Cliffside Resort Condominiums

3. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is CA $339
CA $742 total
includes taxes & fees
Sep 9 - Sep 10
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 CA $415
CA $474 total
includes taxes & fees
Oct 1 - Oct 2
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 CA $215
CA $284 total
includes taxes & fees
Oct 4 - Oct 5
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 CA $231
CA $309 total
includes taxes & fees
Sep 21 - Sep 22
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 CA $298
CA $451 total
includes taxes & fees
Sep 9 - Sep 10
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 CA $298
CA $451 total
includes taxes & fees
Sep 9 - Sep 10
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 CA $343
CA $419 total
includes taxes & fees
Sep 7 - Sep 8
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 CA $944
CA $1,744 total
includes taxes & fees
Sep 7 - Sep 8
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 CA $485
CA $813 total
includes taxes & fees
Sep 14 - Sep 15
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 CA $408
CA $849 total
includes taxes & fees
Sep 13 - Sep 14
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
The price is CA $900
CA $2,010 total
includes taxes & fees
Sep 28 - Sep 29
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 CA $593
CA $2,380 total
includes taxes & fees
Sep 9 - Sep 10
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 CA $196
CA $239 total
includes taxes & fees
Sep 29 - Sep 30
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 CA $270
CA $579 total
includes taxes & fees
Sep 14 - Sep 15
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 CA $243
CA $494 total
includes taxes & fees
Sep 13 - Sep 14
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 CA $298
CA $468 total
includes taxes & fees
Sep 9 - Sep 10
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 CA $298
CA $468 total
includes taxes & fees
Sep 9 - Sep 10
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wainscott Woods vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Wainscott Woods vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wainscott Woods vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wainscott Woods vacation rentals we have selected for you start as low as CA $239 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wainscott Woods rentals

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

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 vacation rental in Wainscott Woods?

Yes, we have vacation rentals near the most popular attractions in Wainscott Woods, or you can go with a secluded option if you want a relaxing place to stay.

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

The Hampton Sack a cheerful relaxing beach cottage: This vacation home rental near Wainscott Woods is equipped with a barbecue grill, 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 vacation rentals are there in Wainscott Woods?

With 18 Expedia vacation rentals, you're sure 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 larger area.

What’s a vacation rental in Wainscott Woods like?

A vacation rental is a private property you can stay in for a couple of days or more in Wainscott Woods. Vacation rentals feature extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.