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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, (1023)
"Best affordable hotel in Montauk"
The price is NZ$590
includes taxes & fees
3 Jun - 4 Jun
Montauk Manor
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (237)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is NZ$486
includes taxes & fees
3 Jun - 4 Jun
Windward Shores Ocean Resort
The Surf Club
3.5 star property
8.4 out of 10, Very good, (220)
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is NZ$527
includes taxes & fees
17 Jun - 18 Jun
The Surf Club
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Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, (299)
"It was so close to town!"
The price is NZ$356
includes taxes & fees
5 Jun - 6 Jun
Montauk Oceanside Suites
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (187)
"Such a nice weekend getaway. We probably rented the smallest of the rooms but it was still comfortable and accommodating. Had a mini kitchen that was perfect for us. ALL the staff were so friendly and helpful. I enjoyed the communications through text to set up room service and beach chairs for the next day. The heated pool was an absolute plus and so was the pool playing by the pool. Made us feel like we were away on an all inclusive vacation. "
The price is NZ$335
includes taxes & fees
2 Jun - 3 Jun
Driftwood Resort
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 NZ$580
includes taxes & fees
23 Jun - 24 Jun
Cliffside Resort Condominiums
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, (11)
"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
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (48)
"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
Newly Renovated Montauk Condo with Ocean Views!
9.6 out of 10, Exceptional, (63)
"Pictures don’t do it justice! So relaxing. Quiet and clean. Best we could ask for. The deck is great. It was bit cold so we couldn’t use the pool but we would love to be back for the summer! Very close to close to everything but still extremely quiet. Kelly was also an amazing host. She responded quickly and assisted with a parking question we had. Couldn’t ask for anything more. 5 stars!"
Newly Renovated Montauk Condo with Ocean Views!
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (73)
"We had the best time at Rick’s house in the Hamptons! We’d love to come back!"
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
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
MONTAUK MANOR-DELUXE STUDIO APARTMENT
10.0 out of 10, Exceptional, (54)
"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)
"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!
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!
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!
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"
The price is NZ$979
includes taxes & fees
13 Jun - 14 Jun
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
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
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
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
Secluded 1 Br Cottage on the Lake, Close to Ditch with OS Shower & Fabulous Yard
9.8 out of 10, Exceptional, (31)
"The cabin was cosy and functional, and in a quiet location. Very happy."
Secluded 1 Br Cottage on the Lake, Close to Ditch with OS Shower & Fabulous Yard
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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)
"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 NZ$671
includes taxes & fees
2 Jun - 3 Jun
The Wainscott Inn
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 NZ$1,254
includes taxes & fees
2 Jun - 3 Jun
Gurney's Montauk Resort & Seawater Spa
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 NZ$413
includes taxes & fees
3 Jun - 4 Jun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Wainscott holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Wainscott. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Wainscott. Seeing all the best attractions is bound to make you fall in love with Wainscott. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Wainscott short-term rentals, that won’t be hard to do.

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?

Montauk Cozy Beach Studio. Walk to private ocean beach & always pet friendly!: This holiday home rental outside of Wainscott offers 1 hot tub, a BBQ 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 holiday rentals are there in Wainscott?

Expedia has 34 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.

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