Wainscott Vacation Rentals

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Our top choices for Wainscott vacation rentals

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is CA $2,043
CA $2,659 total
includes taxes & fees
Feb 8 - Feb 9
Cozy 5 Bedroom With Wi-fi And Air Condition

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,292 reviews)
"Nice pool, great restaurant "
United States
April
The price is CA $190
CA $243 total
includes taxes & fees
Feb 12 - Feb 13
Montauk Manor

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (305 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
The price is CA $180
CA $236 total
includes taxes & fees
Feb 9 - Feb 10
Windward Shores Ocean Resort

Seabreeze #3: Cozy Cottage by the beach

Seabreeze #3: Cozy Cottage by the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is CA $75
CA $622 total
includes taxes & fees
Feb 9 - Feb 10
Seabreeze #3: Cozy Cottage by the beach

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Hampton Bays
9.6 out of 10, Exceptional, (15 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is CA $135
CA $1,648 total
includes taxes & fees
Feb 9 - Feb 10
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Cottage on Beach front Estate with Dockage .Walk to Village

Cottage on Beach front Estate with Dockage .Walk to Village
Pipes Cove
10.0 out of 10, Exceptional, (75 reviews)
"Wonderful stay at such a special spot. "
United States
Meg B.
The price is CA $410
CA $534 total
includes taxes & fees
Feb 28 - Mar 1
Cottage on Beach front Estate with Dockage .Walk to Village

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is CA $369
CA $791 total
includes taxes & fees
Feb 10 - Feb 11
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Hampon Bays
9.6 out of 10, Exceptional, (23 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is CA $135
CA $1,811 total
includes taxes & fees
Feb 18 - Feb 19
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

East Hampton Estate for 8, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 8, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
The price is CA $135
CA $825 total
includes taxes & fees
Feb 13 - Feb 14
East Hampton Estate for 8, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is CA $149
CA $256 total
includes taxes & fees
Feb 8 - Feb 9
American Beech in Greenport - Petite King Room 7

Blackberry: Private home with jacuzzi year-round

Blackberry: Private home with jacuzzi year-round
East Hampton
9.0 out of 10, Wonderful, (4 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 $135
CA $1,337 total
includes taxes & fees
Feb 8 - Feb 9
Blackberry: Private home with jacuzzi year-round

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.0 out of 10, Wonderful, (10 reviews)
"Enjoyed our time. House was clean, pool was a bonus for the family after a day at the beach. House was spacious and welcoming. Beds were very comfortable.Location was perfect! Would definitely come back!"
United States
Panagiota K.
The price is CA $363
CA $991 total
includes taxes & fees
Feb 9 - Feb 10
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
The price is CA $655
CA $905 total
includes taxes & fees
Feb 8 - Feb 9
Offshore Residences

Beach cottage, private road, private beach, private mooring, private parking.

Beach cottage, private road, private beach, private mooring, private parking.
Laurel
10.0 out of 10, Exceptional, (1 review)
The price is CA $369
CA $1,108 total
includes taxes & fees
Feb 16 - Feb 17
Beach cottage, private road, private beach, private mooring, private parking.

Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (5 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is CA $412
CA $855 total
includes taxes & fees
Feb 8 - Feb 9
Northfork Townhouse walk to all

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (10 reviews)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
The price is CA $338
CA $760 total
includes taxes & fees
Feb 8 - Feb 9
Renovated Townhouse walk to all

Seabreeze #4: Charming Cottage Footsteps to the Beach

Seabreeze #4: Charming Cottage Footsteps to the Beach
Hampton Bays
8.8 out of 10, Excellent, (3 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is CA $103
CA $658 total
includes taxes & fees
Feb 18 - Feb 19
Seabreeze #4: Charming Cottage Footsteps to the Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Water Mill
10.0 out of 10, Exceptional, (6 reviews)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is CA $4,103
CA $7,945 total
includes taxes & fees
Mar 1 - Mar 2
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is CA $444
CA $880 total
includes taxes & fees
Feb 8 - Feb 9
Immaculate Waterfront 2 bedroom!

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (3 reviews)
"perfect for families"
United States
Okito H.
The price is CA $615
CA $1,517 total
includes taxes & fees
Feb 9 - Feb 10
Minutes from the beach, brand new 4 bedroom
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Wainscott?

Yes, we have vacation rentals near well known points of interest in Wainscott, or you can choose a 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 coffeehouses during your trip.

What's the top vacation rental that Wainscott has to offer?

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!: This vacation home near Wainscott is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Wainscott?

Expedia has 37 vacation rentals for your stay in Wainscott.

What can I see and do in Wainscott?

Explore the area and family-friendly sights such as Railroad Museum of Long Island, or get out into nature at a spot like The Hamptons Beaches. In the larger area, you’ll find Georgica Beach and Wolffer Estates Vineyard.

What are vacation rentals like in Wainscott?

Vacation rentals are privately owned properties you can book for a short or long stay in Wainscott. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for small groups.