Photo by Miriam Marcus

Wainscott Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
3 Nov - 4 Nov
Tomorrow
4 Nov - 5 Nov
This weekend
7 Nov - 9 Nov
Next weekend
14 Nov - 16 Nov

Holiday Rentals in Wainscott

5 bedrooms, desk, iron/ironing board, travel cot
Prime location! Walk to Beach! Wainscott Family House & Cottage. Pool & Hot Tub!
Prime location! Walk to Beach! Wainscott Family House & Cottage. Pool & Hot Tub!
9.8 out of 10, Exceptional, (29)
"Perfect location for a family trip! Great property to just hang by the pool & enjoy the large back yard. Nice bike ride past a farm stand to get to the beautiful beach. Love the surrounding farms & proximity to the beach"
United States
Catherine D.
Prime location! Walk to Beach! Wainscott Family House & Cottage. Pool & Hot Tub!
Front of property – evening/night
Montauk Manor
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1260)
"Idillic property, very relaxing, with a wonderful view. We stayed only one night so we did not try the restaurant or the pool but we enjoyed the stay. "
United States
Lydia
Montauk Manor
Private kitchen
Montauk Oceanside Suites
Montauk Oceanside Suites
3.0 star property
8.6 out of 10, Excellent, (415)
"We loved it, suite size was great! "
United States
Patrick
Montauk Oceanside Suites
Beach nearby
Cliffside Resort Condominiums
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (245)
"Nice location and good for staying with families. The rooms could have been a little cleaner and updated. Hotel communication was excellent for checking in. "
United States
dean
Cliffside Resort Condominiums
Living area
Windward Shores Ocean Resort
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (303)
"Loved the balcony view….wrong season for swimming but pool looks inviting"
United States
Brenda
Windward Shores Ocean Resort
Private kitchen
Driftwood Resort
Driftwood Resort
3.5 star property
9.0 out of 10, Wonderful, (235)
"Great place for families and to enjoy the beauty of Montauk without being in Montauk town. Beautiful beach next to a state park so feels secluded and not crowded. Highly recommend!!!"
United States
Angel
Driftwood Resort
Outdoor pool, a heated pool
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
2.5 star property
9.6 out of 10, Exceptional, (16)
"A new clean cozy space. Perfect for a weekend getaway. Very easy experience. Highly recommended!"
United States
John W.
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Living area
Offshore Residences
Offshore Residences
4.5 star property
Offshore Residences
Outdoor pool, a heated pool
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
10.0 out of 10, Exceptional, (89)
"Great house with awesome backyard, host responsive and very easy to work with! Would stay again!"
United States
Kilee B.
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Terrace/patio
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
9.6 out of 10, Exceptional, (142)
"Had a lovely time at our stay! Only regret was that we couldn’t stay longer, there were so many amenities we couldn’t take full advantage of. Such a beautiful property!"
United States
Gina K.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Interior
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.4 out of 10, Exceptional, (40)
"we had a lovely stay in this apartment! it was very spacious and comfortable. The pull out couch was also surprisingly very comfy! Mark and Nancy were very responsive and helpful. "
United States
Madison
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
On the beach, white sand
The Surf Club
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (280)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The Surf Club
Smart TV, fireplace, stereo
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
10.0 out of 10, Exceptional, (95)
"Property was great! Rick was super responsive. It was a great trip to the Hamptons! "
United States
colin f.
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Outdoor pool, a heated pool
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
9.8 out of 10, Exceptional, (32)
"This place was so nice and so close to so many fun places! "
United States
Daniella L.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
1 bedroom, WiFi, bed sheets
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
10.0 out of 10, Exceptional, (60)
"Amazing stay…. Great host, excellent location and very clean!"
Australia
Amy W.
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
Interior
MONTAUK MANOR-DELUXE STUDIO APARTMENT
MONTAUK MANOR-DELUXE STUDIO APARTMENT
9.8 out of 10, Exceptional, (76)
"We were so excited to come back to this property after our lovely stay in february! We had an amazing time again and loved it! "
United States
Katie M.
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Outdoor dining
Cottage on Beach front Estate with Dockage .Walk to Village
Cottage on Beach front Estate with Dockage .Walk to Village
10.0 out of 10, Exceptional, (72)
"Wonderful stay at such a special spot. "
United States
Meg B.
Cottage on Beach front Estate with Dockage .Walk to Village
TV, fireplace, video library, stereo
Stunning Hampton Holiday Family Fantasy for your Team
Stunning Hampton Holiday Family Fantasy for your Team
9.8 out of 10, Exceptional, (74)
"We loved the house. We had a large party and did alot of cooking - the kitchen was top notch. Great supplies - lots of room and all appliances were excellent. All the rooms were great beds comfy towels great. "
United States
Lois W.
Stunning Hampton Holiday Family Fantasy for your Team
Beach nearby, sun-loungers, beach towels
Newly Renovated Montauk Condo with Ocean Views!
Newly Renovated Montauk Condo with Ocean Views!
9.8 out of 10, Exceptional, (84)
"We had a great time relaxing and taking quiet walks on the beach. The beach access was very close and very quiet. "
United States
Shawn B.
Newly Renovated Montauk Condo with Ocean Views!
Terrace/patio
American Beech in Greenport - Petite King Room 7
American Beech in Greenport - Petite King Room 7
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
American Beech in Greenport - Petite King Room 7
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wainscott Hotel Reviews

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"It was clean and the staff was very nice they "
Fran 1-night trip
Posted 20 hours ago
The Bentley Hotel Southampton

Find out more about Wainscott

Search for holiday rentals in Wainscott on Expedia! You can easily find your home rentals, villas, holiday apartments in Wainscott using one of the methods below:

  • View our selection of featured holiday rentals in Wainscott
  • Use the map to find apartments and other holiday homes in the Wainscott neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Wainscott while they last

Look no further and take a look at our great range of rental properties in Wainscott!

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?

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : This holiday home rental outside of Wainscott offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Wainscott?

Expedia has 37 holiday 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 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.