Wainscott Vacation Rentals from ￥26,224: Search Short-Term Rentals

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Our top choices for Wainscott vacation rentals

A kitchen with a central island, white cabinetry, and a brick accent wall.

1. Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

Wainscott

Suzanne B.

￥340,728 total

includes taxes & fees

Nov 12 - Nov 13

A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

2. Charming Accommodations in the Hamptons

Sag Harbor

￥82,318 total

includes taxes & fees

Nov 2 - Nov 3

3. Driftwood Resort

Montauk

Julian

￥27,471 total

includes taxes & fees

Oct 31 - Nov 1

A spacious hallway with high ceilings, arched columns, and chandeliers.

4. Montauk Manor

Montauk

Maria

￥28,051 total

includes taxes & fees

Nov 30 - Dec 1

5. Windward Shores Ocean Resort

Napeague

Banessa

￥28,019 total

includes taxes & fees

Nov 1 - Nov 2

A modern living room with a wooden accent wall, a flat-screen TV, a fireplace, and a dining area with a chair and table.

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

Bridgehampton

Katie B.

￥92,650 total

includes taxes & fees

Nov 8 - Nov 9

A dining area with a round table, six chairs, and a chandelier.

7. Year round Jacuzzi - Blackberry East Hampton Home

East Hampton

Suzanne R.

￥230,463 total

includes taxes & fees

Nov 8 - Nov 9

A small cabin with a porch, surrounded by trees and a fenced area.

8. Lovely studio with AC in charming Sag Harbor

Sag Harbor

"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...

Emily t.

￥82,318 total

includes taxes & fees

Nov 2 - Nov 3

A balcony with a view of the ocean, a lawn, and a house in the background.

9. Cliffside Resort Condominiums

Greenport

William

￥47,937 total

includes taxes & fees

Nov 15 - Nov 16

A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

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

Southampton

Justin

￥89,072 total

includes taxes & fees

Nov 1 - Nov 2

A beach with footprints leading to the water, a sunset in the background, and a clear sky.

11. Steps to the beach | Seabreeze Cottage #3

Hampton Bays

"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and...

Lydia

￥76,620 total

includes taxes & fees

Nov 1 - Nov 2

12. Montauk Oceanside Suites

Downtown Montauk

Jadana

￥26,224 total

includes taxes & fees

Nov 1 - Nov 2

A spacious living area with a large bed, a dining table, and a kitchen in the background.

13. Unit 1021: Studio | 2nd Floor-Pool View | Starfish

Napeague

Liana T.

￥77,903 total

includes taxes & fees

Oct 31 - Nov 1

A compact kitchen with a dining table, chairs, a refrigerator, a stove, and a hanging light fixture.

14. Cozy Cottage by the beach - Seabreeze #1

Hampton Bays

￥76,620 total

includes taxes & fees

Nov 30 - Dec 1

15. The Surf Club

Montauk

na

￥49,325 total

includes taxes & fees

Nov 5 - Nov 6

A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

16. The SandPiper

Pipes Cove

Manuela C.

￥38,278 total

includes taxes & fees

Nov 10 - Nov 11

A backyard with a swimming pool, wicker lounge chairs, and potted plants.

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

Sag Harbor

maria m.

￥171,982 total

includes taxes & fees

Oct 31 - Nov 1

A modern house with a deck, outdoor seating, and a fire pit.

18. North Fork Resort

Greenport

Altynai

￥55,947 total

includes taxes & fees

Nov 1 - Nov 2

A beach with people relaxing on chairs and sunbathing.

19. Harbor Heights

Pipes Cove

Steven R.

￥38,278 total

includes taxes & fees

Nov 10 - Nov 11

A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

20. Aqua Vista

Pipes Cove

Kerri L.

￥40,170 total

includes taxes & fees

Nov 9 - Nov 10

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Top Wainscott Hotel Reviews

Montauk Blue Hotel

8/10 Good

"The stellar location, directly on the beach yet walking distance to town, the updated room, the beautiful indoor pool/hot tub enclosure and friendly, responsive staff made our October visit a wonderful experience. Seeing and hearing the ocean, in addition to being able to view the sunset/sunrise from our sliding door, all for a reasonable price, made this hotel a treasure. Updating the room WiFi and as well as the bathrooms at the pool would be a plus. Otherwise, it was perfect!"

Sun N Sound

10/10 Excellent

"I loved it here. The suite I stayed in was clean and the was no issue with parking. The back sitting area was right on the water which was amazing to watch the sunset. I really enjoyed my time at this property. You need a car or uber because nothing was really walkable from here but it was nice to stay on the other side of town. Ill def be back there again!"

Montauk Yacht Club

10/10 Excellent

"The room we stayed in definitely needed maintenance. Frayed carpet edges, unaligned tiles, excessive caulking, calcium buildup, etc. but it was spacious and aesthetically pleasing. However the stay was so relaxing and beautiful even in October. The view was just gorgeous and all the staff was extremely helpful and pleasant. As a nontraditional couple I was extremely pleased with the positive treatment we received. The grounds were well maintained and the spa was amazing. I just got glowing reviews from the people who received the massages and the masseuse really cares for her craft. The food was really fresh and filling. The smoothies were amazing and the vodka pasta met the hype from the reviews. It was an extremely relaxing stay with beautiful views. Will come again."

Zey Hotel

10/10 Excellent

"The stay was perfect. I can't think of a single thing to criticize. As an example, when we were checking out, we called the manager on his cell to alert him that a fire truck was flushing the street hydrants, and that we noticed that the water in the room was brown. We knew that the maintenance of the hydrants was causing the dirty water. The manager promptly told us we could stay until 6:00 pm for free, so that we would be able to take clean showers. We told him that we had showered early, and that we had no problem. But his response showed how he cared for the guests."

Find out more about Wainscott

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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?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This vacation home rental near Wainscott is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

How many vacation rentals are there in Wainscott?

Expedia has 39 vacation rentals for your stay in Wainscott.

What can I see and do in Wainscott?

Explore the area and family-friendly sights such as East End Seaport Maritime Museum, 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.

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Check prices for these dates

Our top choices for Wainscott vacation rentals

1. Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

2. Charming Accommodations in the Hamptons

3. Driftwood Resort

4. Montauk Manor

5. Windward Shores Ocean Resort

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

7. Year round Jacuzzi - Blackberry East Hampton Home

8. Lovely studio with AC in charming Sag Harbor

9. Cliffside Resort Condominiums

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

11. Steps to the beach | Seabreeze Cottage #3

12. Montauk Oceanside Suites

13. Unit 1021: Studio | 2nd Floor-Pool View | Starfish

14. Cozy Cottage by the beach - Seabreeze #1

15. The Surf Club

16. The SandPiper

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

18. North Fork Resort

19. Harbor Heights

20. Aqua Vista

Find vacation rentals that suit your style

Top Wainscott Hotel Reviews

Montauk Blue Hotel

Faraway Sag Harbor

The Bentley Hotel Southampton

Sun N Sound

Montauk Yacht Club

Zey Hotel

The Sagaponack

Offshore Montauk

Ocean Vista Resort

Find out more about Wainscott

Frequently asked questions

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