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Wainscott Holiday Rentals

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Holiday Rentals in Wainscott

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1256)
"Beautiful grounds, excellent staff"
United States
Jess
The price is AU$386
includes taxes & fees
7 Nov - 8 Nov
Montauk Manor
Montauk Oceanside Suites
3.0 star property
8.6 out of 10, Excellent, (415)
"We loved it, suite size was great! "
United States
Patrick
The price is AU$256
includes taxes & fees
20 Oct - 21 Oct
Montauk Oceanside Suites
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (243)
"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
The price is AU$460
includes taxes & fees
2 Nov - 3 Nov
Cliffside Resort Condominiums
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (298)
"Loved the balcony view….wrong season for swimming but pool looks inviting"
United States
Brenda
Windward Shores Ocean Resort
Driftwood Resort
3.5 star property
9.0 out of 10, Wonderful, (235)
"Great place to stay for small family "
United States
DongHo
The price is AU$303
includes taxes & fees
20 Oct - 21 Oct
Driftwood Resort
The SandPiper
9.8 out of 10, Exceptional, (27)
"My wife and I stayed at the Sandpiper for a long weekend. The property was very clean with a warm welcoming feeling. It is within walking distance to the beach and downtown shopping. Great location. I would recommend it to everyone."
United States
steve
The SandPiper
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
8.8 out of 10, Excellent, (28)
"This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!...
United States
Allie G.
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (280)
"Very close walk to the beach great for little ones "
United States
Cara Ann
The Surf Club
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
2.5 star property
9.6 out of 10, Exceptional, (15)
"We had a one-night stay at this location. It was perfect for us from many perspectives and we enjoyed staying there. Very nice place!Thanks! "
United States
James S.
The price is AU$596
includes taxes & fees
27 Oct - 28 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
MONTAUK MANOR-DELUXE STUDIO APARTMENT
9.8 out of 10, Exceptional, (75)
"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
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
9.6 out of 10, Exceptional, (140)
"Perfect property to hangout and stay entertained for hours"
United States
Ryder I.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Offshore Residences
4.5 star property
The price is AU$1,106
includes taxes & fees
19 Oct - 20 Oct
Offshore Residences
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
9.8 out of 10, Exceptional, (32)
"Wonderful outdoor space and great pool. Host was responsive and property was close to all things needed and wanted! Great rental for families."
United States
Patricia Fox M.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
9.8 out of 10, Exceptional, (107)
"Very walkable charming stay in beautiful area that supports larger group. Carter is very responsive and friendly. "
United States
Kendall M.
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Fairy Tale Guest Cottage in Magic Garden by Pool
10.0 out of 10, Exceptional, (76)
"It was a beautiful cottage on a gorgeous property with gracious hosts. I recommend it!!!!"
United States
Lisa
Fairy Tale Guest Cottage in Magic Garden by Pool
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
10.0 out of 10, Exceptional, (95)
"We loved our stay - it was nice to be a short walk away from the bay and the pool was great. The home was very clean and comfortable."
United States
Katie C.
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Work and Play Special! Extended Stay Discount
10.0 out of 10, Exceptional, (52)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
The price is AU$2,234
includes taxes & fees
5 Nov - 6 Nov
Work and Play Special! Extended Stay Discount
Newly Renovated Montauk Condo with Ocean Views!
9.8 out of 10, Exceptional, (83)
"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!
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.4 out of 10, Exceptional, (40)
"Everything was great, thanks so much."
United States
Guy B.
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
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
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

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, 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 favourite 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 depend 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 AU$256 per night. Entering your travel dates in the search wizard might find you 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?

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available : This holiday home rental outside of Wainscott is located near the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games 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 Georgica Beach. In the wider area, you’ll find Wolffer Estates Vineyard and East Hampton Main Beach.

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.