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Vacation rentals in Wainscott

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Top-rated vacation rentals in Wainscott

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Home in Sag Harbor

4.97 out of 5 average rating, 128 reviews

Relax into Coastal Life at a Sun-Drenched Sag Harbor Home

Take a bike ride to Havens Beach and feel the sand in your toes. Walk to explore the shops, restaurants and bars on the quaint Main Street of Sag Harbor. Repair to your sun drenched home away from home to enjoy a relaxed meal alfresco on the deck. Unwind under the umbrellas on the expansive deck surveying the private fenced in backyard. Take in all the amenities of a newly renovated home situated in the Hampton - recent updates include a furnished basement, ping pong table, smart TVs and sound system. Extra touches include beach towels, beach chairs, bikes, cooler, games and more. This beautifully renovated 3 BR, 2 Bath home is situated on a quiet street, with a fenced half acre yard. It is located less than a mile to the shops, bars and restaurants of Main Street and the Hampton Jitney stop with service to NYC. The open floor plan boasts an abundance of natural light with 4 skylights and large windows to bring the outdoors in. Brand new appliances, custom kitchen cabinets, large center island with bar stools are perfect for hosting friends & family. Central AC/forced air heating controlled by the Nest ensure your complete comfort. The master BR features a king bed and ensuite Bath with custom tile shower. The guest BRs have a queen bed and full bed respectively and share the hall bathroom with tub/shower. The large deck runs the length of the home and is perfect for al fresco dining & entertaining. Totally furnished with everything you need to enjoy yourself from the second you enter the home! We have four brand new adult bikes, helmets and locks for your enjoyment. Explore the village, bike to the beach or get some exercise while you're here. If you prefer to stay in, you'll find a games console / DVD player in the front room with a good selection of games and movies. Additionally, we provide 4 beach chairs, beach towels and a small cooler for your use. Enjoy! Guests have access to the entire house, backyard, deck, garage and driveway parking. We can be reached via cell or email and are very responsive. We will also have a friend who is local to the area who will be able to assist with any issues. Sag Harbor is the coolest, most authentic town in the Hamptons. Home to household names, the town retains its small-town charm and rustic maritime vibe. Browse the artsy, eclectic stores and strike up conversations in the coffee shops and local bars. Sag Harbor is a quaint, walkable town on the wharf with great restaurants and bars. The house is located less than a mile's walk into the main street. Beaches are accessible via bike or car. The Jitney stop from Manhattan is located on Main Street less than a mile from the house. There are taxis in the area available via phone for pick up. We provide four adult bikes, helmets and locks for your use.

Home in East Hampton

4.94 out of 5 average rating, 207 reviews

Private beach Historical House with large property

Entire three-story house. 3 large bedrooms and 3 FULL BATHROOMS on a very private, 2+acre wood lot on the bay in Historical East Hampton with private beach access. Fully renovated in 2018 with modern amenities while preserving the original charm. A/C and heating. Private upper floor with bedroom + sitting area for office and extra sleeping. Modern kitchen with island that opens to living room with fireplace. Walk through the secluded backyard to enjoy the amazing sunsets. Ideal for fishing.

Guest suite in Sag Harbor

4.88 out of 5 average rating, 314 reviews

Artists Sag Harbor Village Retreat

January special -book second night for $125! This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Ideal for a fall or winter visit to explore the area during the quieter season. Main Street is lively and all restaurants are open. Central heat & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.

Vacation home in East Hampton

4.8 out of 5 average rating, 106 reviews

Unit 15- New beautiful East Hampton Private Apt!

Our newly built, gorgeous chic units are located in the beautiful, iconic Village of East Hampton. Just 4 minutes from the shop & restaurant lined Village. Close to the beach, & just a short drive to Montauk! Dine at one of the fabulous restaurants in town, or indulge in one of the many boutiques. Come stay with us in our recently built and expertly curated units. All units feature a brand new memory form mattress, new kitchen, wifi, smart TV and all essentials. We look forward to hosting you!

Apartment in Sag Harbor

4.96 out of 5 average rating, 136 reviews

Hamptons Hills Escape

Located in a quiet and safe neighborhood tucked into the woods of Sag Harbor, yet just a 10-minute drive from Sag Harbor town. Down the road is "Morton's Wildlife Refuge" with a beautiful walk to a beach and where birds eat seed directly from your hand. The lovely Long Beach is 5 minutes away - day passes are available. You only have one entrance/exit to deal with, the white door at the top of the wooden stairs that are pictured. Perfect for a couple looking to cook, relax, and spin records.

Home in East Hampton

4.95 out of 5 average rating, 377 reviews

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and check-out are NOT available in season

Guest suite in East Hampton

4.96 out of 5 average rating, 144 reviews

Be our guest! Peaceful private proximity to all.

Beautiful, bright, spacious king suite w fireplace, two bathrooms & private separate poolside entrance, in the country. We are just minutes to golf, hiking, biking, yoga, wineries and beaches. Play games, grill poolside or cozy up fireside w a good book or movie! The space is creatively designed with a nod to natural elements and luxe comfort. Sleep your very best on our super deluxe king sized bed w your choice of pillows. Complimentary coffee/tea/snacks and breakfast treats provided.

Home in East Hampton

4.97 out of 5 average rating, 123 reviews

East Hampton (walking distance to village)

Relax by the hot tub and fire pit with local wines or walk to the village for shopping and dining. House is just a few blocks from Serafina and the famous Nick and Toni’s. Complimentary cruiser bikes included to get around town. IGA supermarket is around the corner and gas grill is on site and ready to use. The house is also walking distance to the train station if your coming from Manhattan. The second bedroom features a Murphy Bed that folds out of the wall and over the couch pictured.

Apartment in Sag Harbor

4.99 out of 5 average rating, 139 reviews

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

Home in Greenport

4.94 out of 5 average rating, 142 reviews

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Home in Sag Harbor

4.95 out of 5 average rating, 132 reviews

Luxury Private King Suite + 2 Floor Living Space

Your modern, spacious, sparkling clean guest home has 2 private floors and a private entrance. The bedroom provides luxury and calm as light from the green trees filters in. Watch movies & chill in your living room complete with kitchenette, wine cooler, powder room and adjoining dining space. You’re in a peaceful neighborhood facing a land forest preserve, 5 minutes from bay beaches and the plethora of farm fresh, organic Sag Harbor eateries.

Guest suite in Sag Harbor

4.95 out of 5 average rating, 189 reviews

Cedar Haven In Sag Harbor

This is a large one room studio apartment with private entrance and ensuite bathroom. The unit is private and closed off from the host’s house. The large main room has a queen bed, and a spacious seating area that includes chairs as well as a comfy leather couch. PLEASE NOTE: One night stays are welcomed but there is a higher rate: IN season, (June 1 - Oct 31) the ONE NIGHT RATE is $375 OFF season, (Nov 1 - end of May) the ONE NIGHT RATE is $300

Vacation rentals for every style

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Popular amenities for Wainscott vacation rentals

Free parking on premises

Air conditioning

Stay near Wainscott's top sights

Wölffer Estate Vineyard277 locals recommend

Havens Beach29 locals recommend

Bay Street Theater & Sag Harbor Center for the Arts75 locals recommend

Children's Museum of The East End95 locals recommend

Georgica Beach14 locals recommend

Sag Harbor Whaling and Historical Museum77 locals recommend

Other great vacation rentals in Wainscott

Guest suite in East Hampton

4.89 out of 5 average rating, 226 reviews

Private Cozy Cottage with Pool / Private Beach

Apartment in Sagaponack

4.98 out of 5 average rating, 41 reviews

Hamptons elegant and comfortable apartment

Cottage in East Hampton

5.0 out of 5 average rating, 24 reviews

Chic cottage on lush, secluded acre by the beach.

Cottage in East Hampton

5.0 out of 5 average rating, 32 reviews

Storybook Cottage Seconds to East Hampton Village

Home in East Hampton

5.0 out of 5 average rating, 15 reviews

East hampton 3 bedroom home w/ pool great location

Home in East Hampton

4.95 out of 5 average rating, 56 reviews

Open Breezy Bungalow with Beach Access By Summer

Apartment in Sag Harbor

5.0 out of 5 average rating, 32 reviews

Spacious apartment in Sag Harbor

Bungalow in Montauk

4.93 out of 5 average rating, 57 reviews

Neff Cottage

Quick stats about vacation rentals in Wainscott

Total rentals
280 properties
Rentals with a pool
230 properties have a pool
Pet-friendly rentals
130 properties allow pets
Family-friendly rentals
250 properties are a good fit for families
Total number of reviews
3.4K reviews
Nightly prices starting at
$50 before taxes and fees

Frequently Asked Questions

Are there Wainscott vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 230 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 130 vacation rentals for guests traveling with pets.
Do house rentals in Wainscott have air conditioning?
Absolutely! We offer over 250 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 160 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 250 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 230 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 240 homes with free parking, over 250 homes with wifi, over 250 homes with air conditioning, over 230 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 $120 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 250 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 240 house rentals with free parking in Wainscott. Enjoy a tailored experience with all the comforts you desire.

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