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Wainscott Woods Vacation Rentals

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Vacation Rentals in Wainscott Woods

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1028)
"Montauk Manor is a beautiful property and very well maintained. The views are spectacular. Monty's restaurant had delicious breakfasts and dinners. The pool was very nice. The accommodations were very clean. The outdoor patio was an added bonus. The staff were very pleasant and helpful."
The price is CA $543
CA $646 total
includes taxes & fees
Jun 18 - Jun 19
Montauk Manor
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (240)
"Access to the beach. "
The price is CA $467
CA $563 total
includes taxes & fees
Jun 19 - Jun 20
Windward Shores Ocean Resort
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (224)
"Very nice location and nice condo"
The price is CA $393
CA $523 total
includes taxes & fees
Jun 24 - Jun 25
The Surf Club
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, (306)
"Spacious and clean. Great for the price though you can hear everything in adjoining units, the connecting doors are very thin and have no sound proofing. Great location and check in and check out was a breeze. "
The price is CA $389
CA $458 total
includes taxes & fees
Jun 24 - Jun 25
Montauk Oceanside Suites
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (192)
"Beach access was easy and lounge chairs were accessible."
The price is CA $306
CA $379 total
includes taxes & fees
Jun 20 - Jun 21
Driftwood Resort
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (184)
"quiet"
The price is CA $437
CA $558 total
includes taxes & fees
Jun 18 - Jun 19
Cliffside Resort Condominiums
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, (12)
"Incredible property, incredible people to work with! We this is our second year in a row renting this house for a holiday weekend, and we look forward to renting every year forward! The house itself is stunning, clean and full of activities from the pool, to the tennis court, to the movie room. Rebecca and Shaun are truly a pleasure, and reply immediately to any questions, requests or needs. They even left us a welcome present for returning this year! Thank you for allowing us to have an annual...
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (73)
"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-DELUXE STUDIO APARTMENT
10.0 out of 10, Exceptional, (55)
"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
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, (25)
"House was very clean and host was exceptional. Very relaxing place to stay."
Beautiful Family Home Nestled In The Heart Of Sagaponack
Gorgeous private Hamptons house with pool and volleyball court
7.8 out of 10, Good, (7)
"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
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (51)
"My family and I thoroughly enjoyed our time in Sag Harbor. The home was conveniently located and ideal for our five-day getaway. Daniel was quick to respond and offered excellent recommendations for restaurants and beach spots. The property was beautiful, and the pool provided a tranquil setting. We're eagerly anticipating future trips."
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Location and views! Located directly on Shinnecock Bay!
9.0 out of 10, Wonderful, (13)
"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!
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
9.8 out of 10, Exceptional, (74)
"The condo was very comfortable and had an amazing view; the beach was just across the street, and the town a 15-minute walk. It was perfect for my family of 3. We hope to come back soon!"
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.4 out of 10, Exceptional, (28)
"We stayed here for a 3 night weekend getaway for our 10th wedding anniversary. Plenty to explore, pool was open and weather was just gorgeous. Apartment was clean & cute, decor a lil outdated. Only complaint was the queen bed was very uncomfortable and made noise every time you moved."
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Newly Renovated Montauk Condo with Ocean Views!
9.6 out of 10, Exceptional, (64)
"This property was beautiful and Freddy was great. It had everything we needed and will definitely be staying there again. "
Newly Renovated Montauk Condo with Ocean Views!
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
10.0 out of 10, Exceptional, (4)
The price is CA $3,298
CA $3,939 total
includes taxes & fees
Jun 20 - Jun 21
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
9.8 out of 10, Exceptional, (92)
"Everything about our stay was 5 star. The host and his wife greeted us, made us immediately comfortable, and were available when we had questions. The house was clean, well kept, and had all the amenities one needs to be comfortable, and the pool, jacuzzi and grounds were spectacular. Proximity to the beach and Montauk town were great, and we lacked for nothing. We definitely plan a return trip! Martha and Peter"
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, (86)
"It was a cute cottage, nicely decorated. We were very comfortable. Each bedroom had a private bathroom which was very nice. It was close to downtown Southampton so that was great. The owner checked in and was very helpful. "
The price is CA $1,305
CA $1,704 total
includes taxes & fees
Jun 18 - Jun 19
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Montauk Mansion With Outdoor Pool
9.8 out of 10, Exceptional, (79)
"nice layout, plenty of room, great restaurant on the premises, we had a lovely stay and a great time."
Montauk Mansion With Outdoor Pool
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See all available properties in Wainscott Woods
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 Woods you may be interested in

Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very good, (575)
"."
The price is CA $1,229
CA $1,676 total
includes taxes & fees
Jun 19 - Jun 20
Gurney's Montauk Resort & Seawater Spa
The Bentley Hotel Southampton
2.0 star property
9.4 out of 10, Exceptional, (84)
"Beautiful hotel, everything brand new everything clean staff very friendly and accommodating close to everything"
The price is CA $326
CA $407 total
includes taxes & fees
Jul 15 - Jul 16
The Bentley Hotel Southampton
The Atlantic Hotel
2.5 star property
7.0 out of 10, Good, (779)
"We enjoyed our stay and felt it was good value for the area. "
The price is CA $330
CA $411 total
includes taxes & fees
Jun 18 - Jun 19
The Atlantic Hotel
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 Woods 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 Woods 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 Woods vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Wainscott Woods vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wainscott Woods. 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 Woods 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 Woods vacation rentals we have selected for you start as low as CA $306 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wainscott Woods rentals

At Expedia, we put the best Wainscott Woods 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 Woods 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 Woods 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 Woods. 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 a vacation rental in Wainscott Woods?

Yes, we have vacation rentals near the most popular attractions in Wainscott Woods, or you can go with a secluded option if you want a relaxing place to stay.

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

Montauk Cozy Beach Studio. Walk to private ocean beach & always pet friendly!: This vacation home rental near Wainscott Woods 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 Woods?

With 19 Expedia vacation rentals, you're sure to find just the right place for your Wainscott Woods stay.

What’s there to see and do in Wainscott Woods?

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. Wolffer Estates Vineyard and The Jewish Center of the Hamptons are a couple of places you'll find in the larger area.

What’s a vacation rental in Wainscott Woods like?

A vacation rental is a private property you can stay in for a couple of days or more in Wainscott Woods. Vacation rentals feature extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.

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