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Compare 1472 Vacation Homes in Wainscott with updated reviews, rates, and availability.

Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
8.0 out of 10, Very Good, (1)
"The property was perfect for our needs! My husband was able to work from the desk in the primary bedroom during the day while my mom and I shopped and explored nearby! Our dog LOVED the backyard and space to explore. We didn’t even need to go venture to the nearby dog park, but that was also super close! As out of towners, unfamiliar with locale, we would recommend bottled water for drinking. Everywhere we went was 5-15 min drive, we very much enjoyed our stay and grateful for the opportunity to...
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
Delightful Southampton Retreat with Pool & Outdoor Shower Near Beach & Shopping
10.0 out of 10, Exceptional, (5)
"We loved our stay here! The hosts were very helpful and communicative leading up to and during our short stay. The house was perfect for our family - the pool area is fantastic and being able to grill food at the outdoor kitchen is such a bonus. No back and forth to the house for snacks or drinks! We spent the evening around the fire pit and the extended deck meant that there was plenty of room for us to relax and our kids to play. We also explored the local area and nearby beaches. The property...
Delightful Southampton Retreat with Pool & Outdoor Shower Near Beach & Shopping
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
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Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!
Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, (84)
"Wow! I have heard about the Hamptons all my life and finally got to visit there last weekend. Not only was the house as beautiful and charming as the pictures represented, but the host was wonderful and was very responsive to all of our questions and needs. And the house was located in a great part of town where we could walk to shopping and restaurants. I highly recommend this house as a place to stay in the Hamptons - it has everything we needed and more!"
The price is SAR 2,438
SAR 3,642 total
includes taxes & fees
26 Jum. II - 27 Jum. II
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
10.0 out of 10, Exceptional, (23)
"It was a great weekend"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
Summer in the Hamptons! Beautiful home with pool, hot tub, pirate ship and more!
10.0 out of 10, Exceptional, (68)
"The house was great - just as listed and very comfortable / kid friendly. There wasn't a whole lot to do in the area over the holidays but we enjoyed the house, trampoline and jungle gym."
Summer in the Hamptons! Beautiful home with pool, hot tub, pirate ship and more!
The Hampton Sack a cheerful relaxing beach cottage
7.4 out of 10, Good, (12)
"Awesome break away from reality. Hope to return soon!"
The Hampton Sack a cheerful relaxing beach cottage
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
10.0 out of 10, Exceptional, (33)
"Perfect location!"
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
The SandPiper
9.4 out of 10, Exceptional, (3)
"This listing was exactly as described and was a great little apartment in Greenport with everything we needed. About a 10 minute walk to downtown area which was very convenient. It sits on a busy street so there is some noise from the road but it did not bother us too much and the host provided noise machines in the bedrooms which was very helpful. Overall I recommend this apartment and would definitely stay in the future!"
The SandPiper
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home
10.0 out of 10, Exceptional, (3)
"Very nice property that is incredibly well maintained. We had a nightmare experience on Cape Cod two summers ago and this was just the opposite. Laura was super responsive and the home was everything you see in the photos with absolutely everything we needed for our stay."
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home
Enjoy the North Fork of Long Island at Our Lovely Home
Enjoy the North Fork of Long Island at Our Lovely Home
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!
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
Beautiful remodeled 2 bedroom home — 5 min from the beach! 20 percent for week
9.8 out of 10, Exceptional, (16)
"This property was just what my family and I were looking for. A quaint and quiet house with a small town feel. We stayed for NYE hoping to get away from the loud chaos we’re typically faced with at home and this location fit the bill. Pros: I’m not sure how this changes in the summer months but things were mostly quiet. There are restaurants, coffee, and food shopping all within a 5 minute drive. The home itself is pretty small, so for the 4 of us- husband, 17y/o, 9 y/o, and myself, it was...
Beautiful remodeled 2 bedroom home — 5 min from the beach! 20 percent for week
Prime East Hampton Village Location. Heated Pool. Walk To All!
10.0 out of 10, Exceptional, (10)
"A great house with an even better location. Walkable to town (and ice cream!) which we loved. The pool was awesome and the house was very clean. Thank you for hosting us!"
Prime East Hampton Village Location. Heated Pool. Walk To All!
Charming Hampton Bays Home 5 Mi to Cooper’s Beach
9.6 out of 10, Exceptional, (9)
"my family and i grew up coming to hampton bays - and while myself and my parents have moved away - a family wedding brought us back to the area and we were so happy to stay local in this perfect home. it felt great to be back in the old neighborhood and not have to be cramped at my brothers home just a short 5 minute drive away. i hope we can stay again during our next trip!"
Charming Hampton Bays Home 5 Mi to Cooper’s Beach
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
10.0 out of 10, Exceptional, (29)
"This was the perfect Christmas House for our family while celebrating a 100th Family Birthday nearby. This is a beautifully appointed and true to period Victorian. The home is immaculate and incredibly well tended. The hosts were lovely and very responsive. This was a special stay and made more so by the wonderful surroundings and ease to town. We would stay here again."
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
Sea Breeze Paradise: Beachfront & Panoramic Views
9.4 out of 10, Exceptional, (16)
"We've found that fall is a great time to visit the North Fork and the property was the perfect place for relaxing. Even when the weather was bad, we had the indoor fireplace to add ambiance and then the outdoor firepit when the weather cleared up. The views are fantastic and so nice to sit outside and relax at night. Had a couple of quick questions come up but got responses very quickly and it didn't interrupt the trip. We had a great time."
Sea Breeze Paradise: Beachfront & Panoramic Views
Respite Ranch: Private Pool, Hot Tub, Beach Access
10.0 out of 10, Exceptional, (2)
"Great stay and wonderful property. The first stay that didn’t have a book and list full of restrictions and checkout instructions. After a whirlwind weekend celebrating our daughter ‘s engagement, this was a welcomed surprise! Everyone enjoyed their stay, including our two labs. Great fenced in yard that gave them plenty of room to exercise. We will be back!"
Respite Ranch: Private Pool, Hot Tub, Beach Access
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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 property types in Wainscott

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1023)
"Best affordable hotel in Montauk"
The price is SAR 1,121
SAR 1,353 total
includes taxes & fees
3 Jum. II - 4 Jum. II
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 SAR 906
SAR 1,116 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Windward Shores Ocean Resort
The Surf Club
3.5 star property
8.4 out of 10, Very Good, (222)
"Very nice location and nice condo"
The price is SAR 882
SAR 1,210 total
includes taxes & fees
17 Jum. II - 18 Jum. II
The Surf Club
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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