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Wainscott Vacation Rentals

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Vacation Rentals in Wainscott

Montauk Manor
Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1023)
"Best affordable hotel in Montauk"
The price is ￥46,695
per night
Jun 5 - Jun 6
Montauk Manor
Windward Shores Ocean Resort
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (238)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is ￥37,724
per night
Jun 6 - Jun 7
Windward Shores Ocean Resort
The Surf Club
On the beach, white sand
The Surf Club
3.5 star property
8.4 out of 10, Very Good, (222)
"Very nice location and nice condo"
The price is ￥36,987
per night
Jun 17 - Jun 18
The Surf Club
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Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very Good, (302)
"It was so close to town!"
The price is ￥25,340
per night
Jun 6 - Jun 7
Montauk Oceanside Suites
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (187)
"Well maintained upscale resort. "
The price is ￥25,082
per night
Jun 5 - Jun 6
Driftwood Resort
Cliffside Resort Condominiums
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (183)
"Wonderful stay and super clean! Can’t wait to come back. "
The price is ￥43,835
per night
Jun 27 - Jun 28
Cliffside Resort Condominiums
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Outdoor pool, a heated pool
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, (12)
"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!
Beach nearby, sun loungers, beach towels
Newly Renovated Montauk Condo with Ocean Views!
9.6 out of 10, Exceptional, (63)
"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
Outdoor pool, a heated pool
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (49)
"We had a lovely stay at this home. It was very clean, comfortable and spacious so we could all spread out. We were glad to have a nice warm house to stay in because the weather was terrible! I also went swimming in the warm pool even though it was 60 and raining! Would highly recommend."
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Beautiful Family Home Nestled In The Heart Of Sagaponack
Outdoor pool, a heated pool
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
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Smart TV, fireplace, stereo
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 -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Interior
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.4 out of 10, Exceptional, (27)
"Rainy but good weekend"
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Lobby
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
Location and views! Located directly on Shinnecock Bay!
Smart TV
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (12)
"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
Outdoor pool
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
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
On the beach, sun loungers, beach towels
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
9.8 out of 10, Exceptional, (91)
"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
Lobby
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
4 bedroom 2.5 bathroom A/C Decks Pvt Beach /HotTub/FirePit
Beach nearby
4 bedroom 2.5 bathroom A/C Decks Pvt Beach /HotTub/FirePit
9.8 out of 10, Exceptional, (12)
"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!!!
Outdoor dining
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, (28)
"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!
On the beach
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
9.8 out of 10, Exceptional, (73)
"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
Front of property
The Wainscott Inn
3.0 star property
8.6 out of 10, Excellent, (93)
"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 ￥51,380
per night
Jun 5 - Jun 6
The Wainscott Inn
Gurney's Montauk Resort & Seawater Spa
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very Good, (570)
"Great time beautiful property"
The price is ￥104,712
per night
Jun 16 - Jun 17
Gurney's Montauk Resort & Seawater Spa
The Bentley Hotel Southampton
Terrace/patio
The Bentley Hotel Southampton
2.0 star property
9.4 out of 10, Exceptional, (76)
"Large room recently updated, didn’t hear other guests "
The price is ￥32,159
per night
Jun 23 - Jun 24
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.

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:

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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

Sag Harbor Inn

Sag Harbor Inn

5/5 Excellent
"Perfect location if you're visiting Sag Harbor and want just a short walk to all the restaurants and shopping on Main St. Staff was wonderful, parking was great, and the continental breakfast every morning was a perfect way to start the day. We had a harbor view room which was an absolutely beautiful vista to wake up to. Will be going back at The Sag Harbor Inn for sure."
A verified traveler stayed at Sag Harbor Inn
Posted 20 hours ago
Sag Harbor Inn