Photo by Miriam Marcus

Wainscott Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Wainscott

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, 1,023 reviews
"Best affordable hotel in Montauk"
The price is CA $408
CA $492 total
includes taxes & fees
Jun 5 - Jun 6
Montauk Manor
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, 238 reviews
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is CA $329
CA $405 total
includes taxes & fees
Jun 5 - Jun 6
Windward Shores Ocean Resort
The Surf Club
3.5 star property
8.4 out of 10, Very good, 222 reviews
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is CA $356
CA $480 total
includes taxes & fees
Jun 5 - Jun 6
The Surf Club
Save an average of 15% on thousands of hotels when you're signed in
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, 302 reviews
"It was so close to town!"
The price is CA $221
CA $266 total
includes taxes & fees
Jun 5 - Jun 6
Montauk Oceanside Suites
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, 187 reviews
"Well maintained upscale resort. "
The price is CA $219
CA $279 total
includes taxes & fees
Jun 5 - Jun 6
Driftwood Resort
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, 183 reviews
"Wonderful stay and super clean! Can’t wait to come back. "
The price is CA $383
CA $496 total
includes taxes & fees
Jun 27 - Jun 28
Cliffside Resort Condominiums
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, 12 reviews
"We really enjoyed our stay in this house. Very safe and clean place to stay. Plenty of parking spaces, logs for fireplace, kitchen accessories. All china is very good quality."
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Newly Renovated Montauk Condo with Ocean Views!
9.6 out of 10, Exceptional, 63 reviews
"Loved our stay! Perfect location and the place was very clean."
Newly Renovated Montauk Condo with Ocean Views!
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, 49 reviews
"Close to the restaurants and beaches. We enjoyed exploring the nearby areas within 15 to 30 mins drive"
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, 25 reviews
"House was very clean and host was exceptional. Very relaxing place to stay."
Beautiful Family Home Nestled In The Heart Of Sagaponack
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, 73 reviews
"This place exceeded all expectations, offering a perfect blend of convenience and serenity. Situated just moments from downtown, the location provided easy access to the vibrant community, while still offering a peaceful retreat. The highlight of our stay was undoubtedly the private beach access. Tucked away in a tranquil neighborhood, it boasted unparalleled beauty and tranquility. Simply being in the vicinity was a getaway in itself, with breathtaking views that soothed the soul. The...
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.4 out of 10, Exceptional, 28 reviews
"Rainy but good weekend"
The price is CA $443
CA $816 total
includes taxes & fees
Jun 13 - Jun 14
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
MONTAUK MANOR-DELUXE STUDIO APARTMENT
10.0 out of 10, Exceptional, 55 reviews
"Studio was perfect and grounds of property were breaking. Would definitely stay there again. Got to enjoy Montauk and have a beautiful place to stay."
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, 12 reviews
"You have the opportunity to attend a graduation party at the Hamptons, where everyone had to find their own accommodations. The location is essentially located to town to the water and beautiful scenic paths. The host insured that the home was exceptionally clean and amenities provided. Not to mention accommodating due to last-minute change in schedule."
Location and views! Located directly on Shinnecock Bay!
Gorgeous private Hamptons house with pool and volleyball court
7.8 out of 10, Good, 7 reviews
"This place was nice and roomy for our family of 8 plus 3 littles kiddos. Pretty clean as well. I gave listing accuracy a 5 because it is accurate but that may be because it doesn't tell you much. We were a little short on towels, many light bulbs were burnt out or just missing. We replaced some (they were there) and moved others to balance out the light. No kitchen linens, short on bath towels, short on paper towels and definitely not enough TP. 3 partial rolls and 1 bathroom had none so we had...
Gorgeous private Hamptons house with pool and volleyball court
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
9.8 out of 10, Exceptional, 91 reviews
"Had great time at property. Very close to town and beach. Would highly recommend."
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Montauk Mansion With Outdoor Pool
9.8 out of 10, Exceptional, 79 reviews
"nice layout, plenty of room, great restaurant on the premises, we had a lovely stay and a great time."
Montauk Mansion With Outdoor Pool
4 bedroom 2.5 bathroom A/C Decks Pvt Beach /HotTub/FirePit
9.8 out of 10, Exceptional, 12 reviews
"Loved the location to the beach and neighborhood. Great for a weekend getaway."
4 bedroom 2.5 bathroom A/C Decks Pvt Beach /HotTub/FirePit
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, 28 reviews
"The house was beautiful and comfortable. We enjoyed the property and watching the wildlife. The fire pit was great for a group gathering. We didn't cook but the kitchen appeared well stocked. The house was short on paper products. We left a note for the house manager when we left."
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
9.8 out of 10, Exceptional, 73 reviews
"We enjoyed our stay. No complaints. Great location."
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
Don't see what you're looking for?
See all available properties in Wainscott
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.

Other types of properties in Wainscott you may be interested in

The Wainscott Inn
3.0 star property
8.6 out of 10, Excellent, 93 reviews
"The staff is wonderful and the rooms are nicely decorated. The hotel is going through a renovation so is not very presentable for now but should be all fixed bt July 1st. "
The price is CA $448
CA $559 total
includes taxes & fees
Jun 5 - Jun 6
The Wainscott Inn
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very good, 570 reviews
"Great time beautiful property"
The price is CA $914
CA $1,246 total
includes taxes & fees
Jun 16 - Jun 17
Gurney's Montauk Resort & Seawater Spa
The Bentley Hotel Southampton
2.0 star property
9.4 out of 10, Exceptional, 76 reviews
"Large room recently updated, didn’t hear other guests "
The price is CA $262
CA $359 total
includes taxes & fees
Jun 5 - Jun 6
The Bentley Hotel Southampton
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.

Everything you need to know about Wainscott vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wainscott vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Wainscott vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wainscott vacation rentals we have selected for you start as low as CA $219 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 vacation 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 vacation.

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 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?

Montauk Cozy Beach Studio. Walk to private ocean beach & always pet friendly!: This vacation home rental near Wainscott offers a spa tub, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Wainscott?

Expedia has 34 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.

Recent reviews of Wainscott properties
Expedia verified reviews