Holiday rentals with a patio in Wainscott

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Top-rated rentals with patio in Wainscott

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Guest favourite

Home in Sag Harbor

5.0 out of 5 average rating, 27 reviews

Sag Harbor Modern Oasis

Luxury 5 bedroom, 3 1/2 bathroom home designed around a central courtyard/non heated pool area (5300sqft) Grill & contemporary seating area with fire pit; perfect entertainment area against a backdrop of arboreal gardens. Split across 3 levels; light filled main living, dining and eat in kitchen; two entertainment rooms with built in wet bars. Lower level has 5th bedroom with en-suite and dedicated office.Quiet neighborhood; walkways, bike paths. 5mins by car to Sag town beach. 12mins to village

Guest favourite

Home in East Hampton

5.0 out of 5 average rating, 18 reviews

East Hampton Village 3BR - Walk to Ocean Beaches

Our historic home built in 1888 is right in East Hampton Village. Recently updated, it offers 3 bedrooms, 2 full baths, family room with sofa bed and couch, dining room and kitchen. Cozy and classic are understatements! Easily walk to village shops and gorgeous ocean beaches. Or stay in and BBQ on our patio surrounded by our mature landscaping and charming backyard. Our elegant living space has a Grand Piano and our family room has 2 sets of french doors that open wide to our patio & backyard.

Guest favourite

Loft in Milford

4.94 out of 5 average rating, 99 reviews

Lovely water front lower-level loft, free parking

This unique centrally located water front loft is located on the second Gulf Pond 1.5 miles from historic Milford center buzzing with water front restaurants and downtown shopping. This one bedroom, one bath, has a private entrance and free off street parking. Outdoor patio & grill with kitchenette, enjoy a waterfront view throughout the 400 sq ft space. Close to I-95, the Merrit Parkway, and Milford train station. Explore 17 miles of beaches in this New England town by bike, kayak, or foot.

Superhost

Guest house in Bridgehampton

4.82 out of 5 average rating, 67 reviews

Central Hamptons Guesthouse

This is a quiet + cozy guesthouse located at the rear corner of the property. The Guesthouse is nearby both Bridgehampton and Sag Harbor and has its own private dining and seating area. If you would like to use hot tub it is private for the guesthouse use only, their is also a separate pool area available for guest use however please be respectful of the other guests and the neighbors. The pool also is open for the season as of Mar24 and the hot tub is available for use year around.

Guest favourite

Home in East Hampton

5.0 out of 5 average rating, 19 reviews

Sparkling East Hampton Oasis 3/2, heated pool

This freshly renovated modern beach cottage with serene deck and pool area is nestled on a quiet cul-de-sac in Springs. You'll feel away from it all, but still within a 10 minute drive to towns, beaches, and restaurants. With 3 bedrooms, 2 new baths, and a gorgeous kitchen, the home also boasts 2 separate open living areas. This spot is relaxing and convenient to all the East End offers. Pool can be heated upon request at an additional cost starting Memorial Day! Welcome to Hello Haven!

Guest favourite

Home in East Hampton

5.0 out of 5 average rating, 17 reviews

Stunning 3 BR / 2.5 New Construction with Pool

Conveniently located equidistant to East Hampton and Sag Habor Villages, this 3 BR / 2.5 Bath ranch home on 1.3 acres is set back behind a buffer of trees. Offering approximately 1,700 sq. ft. of living space this L shaped home's open concept living areas flow among the living room with fireplace, dining area and kitchen. The primary suite includes a walk-in closet and luxe bath. 2 additional rooms share a Jack and Jill bath. Outdoors relax on the deck overlooking the inground pool.

Guest favourite

Cottage in Southampton

4.96 out of 5 average rating, 105 reviews

Charming Southampton Light filled Cottage

Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

Superhost

Home in East Hampton

4.87 out of 5 average rating, 15 reviews

East Hampton: Clearwater Beach Pass

Kick back and relax in this calm, stylish space. Charming home located in a private beach community in East Hampton. Home was just redone and is newly remodeled in the quintessential Hamptons style. The open living spaces with high ceilings are filled with natural light and overlook a private garden. Bike or walk a short distance to the beaches, enjoy the secluded backyard, or stroll into town. Perfect for your city escape! Summer and extended seasonal inquiries are welcome.

Guest favourite

Home in East Hampton

5.0 out of 5 average rating, 11 reviews

EH Cottage with Hot Tub and heated pool

This small beach bungalow is the ultimate spot for a family getaway in the Hamptons. An open floor plan and double height beamed ceilings showcase the casual living space that flows seamless into front and back decks and a backyard with tons of amenities 3 bedroom / 2 bathroom - With heated pool & hot tub. Bike or walk to private community beach Sleeps 5 adults or 4 adults and 2-3 kids Private home, no other house on the property, this is not a guest cottage

Superhost

Home in East Hampton

4.89 out of 5 average rating, 28 reviews

⭐Walk to the Village ❤ of East Hampton

Stay in our Cozy Hamptons Cottage, in one of the most central and convenient locations in East Hampton Village! ✔Self Check-in ✔Private Driveway ✔Ideal for Longer Stays & Flexcations ✔Fast Wifi- Perfect for Working Remotely ✔24/7 Customer Support ✔Walking distance to Shopping/Bars/Restaurants & Grocery Store ✔7 min drive to E Hampton Beach ✔Fully stocked Kitchen ✔Complimentary Netflix ✔King Bed ✔Romantic back Garden w/ BBQ ✔Fully Cleaned & Sanitized

Guest favourite

Cottage in East Hampton

5.0 out of 5 average rating, 22 reviews

Chic cottage on lush, secluded acre by the beach.

Charming cottage with spacious lawn surrounded by lush vegetation and protected land. 5-minute walk to a secluded and serene Northwest Harbor beach. An approximately 10-minute drive from both East Hampton and Sag Harbor restaurants and stores. Chic and modern rooms with brand-new, high-end bathrooms. Perfect rental for those who want a mix of quiet time and quick access to everything else. Relax and unwind at this unique and tranquil getaway.

Guest favourite

Guest house in Shelter Island

5.0 out of 5 average rating, 50 reviews

Bayfront 1BR/2BR detached guesthouse with pool

Perfect relaxing getaway for a couple or family. Bayfront 1BR/2BR fully detached guest house with gorgeous morning views. Property has saltwater pool + hot tub (open May -October) and bay access via private dock. Central to both north & south forks (wineries + Hamptons or Montauk just short drive away). Down the road from famous Shelter Island Sunset Beach + golf course. Come explore the beauty of the Hamptons without the stress!