Holiday Rentals Wainscott from £125: Find Short-Term Rentals & Holiday Accommodations

Change your mind
Book hotels with free cancellation
Treat yourself
Save instantly and earn perks with One Key
Learn about One Key
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Wainscott holiday rentals

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

1. !! Rare Two-House Wainscott Estate: Walk to Beach, South of Highway, Wainscott !

Wainscott

Suzanne B.

includes taxes & fees

18 Nov - 19 Nov

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

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

Bridgehampton

Katie B.

includes taxes & fees

15 Nov - 16 Nov

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

3. Charming Accommodations in the Hamptons

Sag Harbor

includes taxes & fees

16 Nov - 17 Nov

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

4. 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.

includes taxes & fees

16 Nov - 17 Nov

A house with a sliding glass door, a white door, and a small porch with potted plants.

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

Sag Harbor

maria m.

includes taxes & fees

15 Nov - 16 Nov

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

6. Montauk Manor

Montauk

barbara

includes taxes & fees

30 Nov - 1 Dec

7. Windward Shores Ocean Resort

Napeague

Banessa

includes taxes & fees

16 Nov - 17 Nov

A modern living room with a flat-screen TV, a dining table with chairs, a sofa, a coffee table, and a chandelier.

8. Luxury Village Rental in the Heart of Sag Harbor

Sag Harbor

includes taxes & fees

15 Nov - 16 Nov

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

9. North Fork Resort

Greenport

Altynai

includes taxes & fees

15 Nov - 16 Nov

10. Montauk Oceanside Suites

Downtown Montauk

Mitchell

includes taxes & fees

15 Nov - 16 Nov

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

11. Cliffside Resort Condominiums

Greenport

William

includes taxes & fees

26 Nov - 27 Nov

A brick patio with outdoor seating, a wooden staircase, and a house with a window and door.

12. Cozy Cottage by the beach - Seabreeze #1

Hampton Bays

includes taxes & fees

19 Nov - 20 Nov

A modern wooden building with large windows, a balcony, and a view of autumn trees.

13. Serene Chic Hamptons oasis jus 1 block to waterfront + 8 minutes to Main Street

East Hampton

includes taxes & fees

14 Nov - 15 Nov

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

14. 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

includes taxes & fees

15 Nov - 16 Nov

A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

15. Minutes from the beach, brand new 4 bedroom

Southampton

Okito H.

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

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

East Hampton

ANGELA S.

includes taxes & fees

1 Dec - 2 Dec

A modern living room with a sofa, armchairs, a coffee table, and a TV.

17. Minutes from the beach, brand new 3 bedroom

Southampton

Kathy B.

includes taxes & fees

24 Nov - 25 Nov

A residential property with a covered patio, outdoor seating, and a hot tub.

18. Jacuzzi year-round - Villa Luz Private Home

Hampon Bays

Annie B.

includes taxes & fees

15 Nov - 16 Nov

A beach with people relaxing on chairs and sunbathing.

19. Harbor Heights

Pipes Cove

Steven R.

includes taxes & fees

22 Nov - 23 Nov

A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a black table set for four.

20. Lovely & Spacious Sag Harbor escape with heated pool

Sag Harbor

includes taxes & fees

16 Nov - 17 Nov

View all properties

Find holiday rentals that suit your style

Top Wainscott Hotel Reviews

An outdoor dining area with trees and tables under string lights.

The 1770 House Restaurant & Inn

East Hampton

10/10 Excellent

Liina

Two bicycles with wicker baskets labeled "Sophie & Co." parked in front of a building with a dark door and white columns.

The Sagaponack

Wainscott

10/10 Excellent

Kerry

A modern building with a wooden exterior, a balcony, and a pathway lined with potted plants and stepping stones.

Journey East Hampton

East Hampton North

10/10 Excellent

Natalie

An outdoor dining area with a table and chairs, surrounded by tall trees and string lights.

A Room At The Beach

Bridgehampton

8/10 Good

Travelled with a friend at the end of Sept . Quiet time for the hotel which is lovely. Good points : stunning garden! Amount of work that it takes to maintain such beautiful plants is impressive . Stylish outdoor furnitures . Bed and pillows were very comfortable . Had a great night sleep . Free water and rose which was a nice touch Improvement points : Eventhough it’s off season , one of the more pricey hotels I’ve ever stayed in prob because of the location .With that price point , there...

Vee Han

A kitchen with a central island, two wicker chairs, and a bar area with glasses.

The Maidstone

East Hampton

8/10 Good

The breakfast had a lot to be desired massive room for choice improvement especially just All Bran!!!! Cold meat and at least a spread is not difficult. Tea and coffee in the room would be good too and would help it live up to its 4* star rating which I would dispute currently. Location is about a 25 minute walk into East Hampton. Food in the evening is extremely expensive and really doesn’t warrant it. Staff could do with some customer relations, but saying that the bar staff were excellent....

Anonymous traveller

A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.

The Bentley Hotel Southampton

Southampton

10/10 Excellent

James

A pool area with umbrellas, potted plants, and a pathway leading to a building.

Faraway Sag Harbor

Sag Harbor

10/10 Excellent

Thoroughly enjoyed my stay at Baron's Cove. I stayed late February so the pool was closed, but this was expected. It's a motel style hotel where your door opens to the outside, but given the location of the hotel i felt perfectly safe. The Staff were fantastic, and always helpful. The breakfast was first class too. Sag Harbor is such an iconic place within the Hamptons and this hotel is just as iconic in my eyes. The decor, is photo-worthy. I certainly hope to come back again soon!

Nathan

A house with a sloped roof, large windows, and a pathway leading to the entrance.

Mill House Inn

Pantigo Road Historic District

10/10 Excellent

Anna

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

The Shoals Suites and Slips

Southold

10/10 Excellent

Paul

Find out more about Wainscott

Everything you need to know about Wainscott 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 holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wainscott holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wainscott. 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 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 holiday rentals we have selected for you start as low as £125 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wainscott rentals

At Expedia, we put the best Wainscott 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 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 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. 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 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?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This holiday home rental outside of Wainscott is located on the beach, and has an outdoor pool, a fireplace and a BBQ 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 holiday rentals are there in Wainscott?

Expedia has 39 holiday 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 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.

Search Holiday Rentals in Wainscott

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Wainscott holiday rentals

1. !! Rare Two-House Wainscott Estate: Walk to Beach, South of Highway, Wainscott !

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

3. Charming Accommodations in the Hamptons

4. Lovely studio with AC in charming Sag Harbor

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

6. Montauk Manor

7. Windward Shores Ocean Resort

8. Luxury Village Rental in the Heart of Sag Harbor

9. North Fork Resort

10. Montauk Oceanside Suites

11. Cliffside Resort Condominiums

12. Cozy Cottage by the beach - Seabreeze #1

13. Serene Chic Hamptons oasis jus 1 block to waterfront + 8 minutes to Main Street

14. Steps to the beach | Seabreeze Cottage #3

15. Minutes from the beach, brand new 4 bedroom

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

17. Minutes from the beach, brand new 3 bedroom

18. Jacuzzi year-round - Villa Luz Private Home

19. Harbor Heights

20. Lovely & Spacious Sag Harbor escape with heated pool

Find holiday rentals that suit your style

Top Wainscott Hotel Reviews

The 1770 House Restaurant & Inn

10/10 Excellent

Find out more about Wainscott

Wainscott holiday rentals: An excellent choice for every season

How to find incredible deals on Wainscott rentals

Frequently Asked Questions

Can I find holiday rentals in Wainscott?

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

How many holiday rentals are there in Wainscott?

What can I see and do in Wainscott?

What are holiday rentals like in Wainscott?

Explore a world of travel with Expedia