
Vacation rentals in Wainscott
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Top-rated vacation rentals in Wainscott
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Popular amenities for Wainscott vacation rentals
Other great vacation rentals in Wainscott

Summer Retreat at the beach , enjoy Wine Country
We had a great stay. The house was warm and inviting. Very peaceful and quiet. Plenty of room for the family. Very easy to get to and very close to downtown. I would highly recommend!!! Steve was very friendly and responsive to all our needs!

A-Frame cabin with private beach & epic sunsets
Amber’s place was immaculate and stunning. This was my 2nd time staying and it was just as magical! The place had plenty of space for a family of 3 and the washer/dryer was very convenient. We had a great time and would stay here again!

Lovely North Fork Beach Cottage (2 BR/2 bath)!
Had a great weekend at the cottage! Meredith was so great letting us check in early and was super helpful and responsive. The cottage is gorgeous and has everything you need. Loved it! Thank you!

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
Had a wonderful time over Easter with my family and dog. The view was exquisite and the house very comfortable. Eileen was very responsive and even had hair dryers sent over. The house was very well equipped with lots of kitchen staple goods. Just be aware there is no microwave, but there is a very nice Breville toaster oven. Also, there is a large table outside for a group, but only a small table and counter seating in kitchen inside. We didn't have any issue since the weather was perfect for us to enjoy our Easter dinner outside. Overall, a beautiful home and only minutes from Greenport and wineries.

Ho Hum Holiday In Bellport with Pool
We needed a dog-friendly ranch style to home with three bedrooms and two bedrooms close to Sayville, where we would be celebrating Thanksgiving. I was lucky enough to find this rental which was clean, comfortable and ideal for our two-night stay. Adam was attentive and easily accessible via text. I would highly recommend this lovely home.

Hamptons Escape minutes from Beaches and Nightlife
Our stay here with our family was absolutely wonderful. The house was so comfortable and spacious and the hot tub in the backyard was a real treat during the off season. The location is great for Hampton Bays beaches and a very quick drive to the popular restaurants in town. Also a nice to drive surrounding towns. Communication with Aida was excellent and she had the hot tub ready to go during check in which was much needed after a long drive. Bedrooms are spacious and the kitchen has all the key equipment to make food at home. Backyard is large and fenced in if you have any pets. We definitely will book again in the future.

Great little place just for a couple
We had a great time staying with Marina. The space was so clean and the perfect size for two adults and our senior pup. The outdoor space was beautifully landscaped and the beach was only a 5 minute walk. We would definitely come back!

Sleek and Chic cottage/Pool House
Perfect getaway in Shelter Island! The pool house is as amazing as it looks in the listing :) Cute house on a beautiful, peaceful and very private green lot. Primael was very welcoming and responsive. She was also very flexible in terms of our check in and check out. Everything went super smoothly. We enjoyed our stay a lot!
Quick stats about vacation rentals in Wainscott
Total rentals
370 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
5.4K reviews
Family-friendly rentals
330 properties are a good fit for families
Pet-friendly rentals
160 properties allow pets
Rentals with a pool
310 properties have a pool
Frequently Asked Questions
Are there Wainscott vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 310 vacation homes with pools in Wainscott, available on Airbnb. Make a splash and soak up the sun in style!
Are there pet-friendly vacation rentals in Wainscott?
Four-legged friends are welcome in Wainscott. Choose from more than 160 vacation rentals for guests traveling with pets.
Do house rentals in Wainscott have air conditioning?
Absolutely! We offer over 330 house rentals with air conditioning in Wainscott. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Wainscott?
Yes! Work meets play with ease at over 220 vacation rentals in Wainscott featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Wainscott have wifi?
Absolutely! We offer over 330 house rentals with wifi in Wainscott. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Wainscott have a kitchen?
Absolutely! We offer over 310 house rentals with a kitchen in Wainscott. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Wainscott?
Enhance your stay in our House Rentals with the most popular amenities: over 330 homes with wifi, over 330 homes with air conditioning, over 320 homes with free parking, over 310 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in house rentals in Wainscott?
Experience the best of Wainscott with our house rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Wainscott?
Wainscott has more than 330 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Wainscott have free parking?
Absolutely! We offer over 320 house rentals with free parking in Wainscott. Enjoy a tailored experience with all the comforts you desire.
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Cooper's Beach, Southampton
- Quotonset Beach
- Giants Neck Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Clinton Town Beach
- Walnut Public Beach
- Amagansett Beach
- Blue Shutters Beach
- Shennecossett Beach
- Connetquot River State Park Preserve
- Long Island Aquarium
- Attawan Beach
- Groton Long Point Main Beach
- Burwells Beach
- Fort Trumbull Beach
- Shoreham Beach
- Bayview Beach
- Wildemere Beach
- Barbara Pine Memorial Beach
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