Vacation rentals in Wainscott

Private beach, fully updated house, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

Location · Family · Laundry

Serene w/ large pool ~1 block to waterfront dining

Serene, chic Hamptons oasis! Ideally located 1 block to waterfront dining + 8 mins. to Main St. + beaches! Enjoy your tranquil home surrounded by nature + privacy. Swim in your pool, spark up the firepit + BBQ under the starry sky! Stream on your 80' TV + cook in your Chef's kitchen. Take a stroll just 1 block away to cafe for morning coffee on the sea and dinner/cocktails watching the sun set over the harbor. Walk home in 4 minutes. Enjoy the peace + calmness right here in your own home!

Location · Family · Decor

Hampton Oasis with private Tennis, Pool, Theater

Private 4800sqf Oasis located between village of East Hampton and Sag Harbor is the perfect summer getaway with US open sized and color Tennis Court, over sized heated Pool, Brand New pool deck! Expansive great room filled with natural sun light , kitchen and dinning with open floor plan perfect for entertaining. The main floor master bedroom with private deck,walk-in closet, double sinks , a soaking tub. There are 4 additional ensuite guest king size bedrooms, HomeTheater,office space,wet bar!

Location · Family · Outdoor spaces

Hamptons Elegant and Comfortable Apartment

Enjoy your stay in this beautifully decorated and completely private basement apartment - with all original artwork- in the center of the Hamptons with the added convenience of being close to major towns and beaches. Large bedroom with comfortable king sized bed and high quality mattress and linen. Large-screen smart TV with many channels. Closet space, well equipped kitchenette, bathroom with glass-enclosed shower. Seating area for 4 and second large-screen smart-TV with comfy oversized couch.

Value · Location · Checkout

Amazing Home close to Everything -

Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grounds are smoke-free.

Family · Location · View

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Value · Location · Indoor spaces

Gated village fringe king ensuite 2 bths prvt pool

Beautiful, bright, spacious King suite w fireplace, 2 en-suite bathrooms & private separate poolside entrance. Pool is 4 u only! We are just minutes to beaches, boating, golf, hiking, biking, yoga and wineries. Solo travelers feel secure here. Play games, grill 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 best on our super deluxe king sized bed w/your choice of pillows. Complimentary coffee/tea/treats

Location · Family · Amenities

Hamptons Dream Suite

Hampton's Dream Suite- Is a guest suite in East Hampton, NY. From relaxing by the pool, to taking a day trip to Montauk, or visiting some of the best beaches in the Hamptons, the opportunities here are endless! It offers a bedroom with a Queen size Select Comfort bed, living room has two queen sofa beds and a full bathroom. It has a Kitchenette, Central AC/Heat with a 65" smart TV with surround sound and DVD, Blue ray and Xbox Games . There is also a TV and blue Ray player in the bedroom.

Family · Location · Nearby

Peaceful cottage

Take a break and unwind at this quiet, peaceful retreat! This 3 level cottage includes lower level garage parking for one car and laundry. The main level holds a full kitchen, spacious living room, and half bath. The second floor bedroom has an en-suite bathroom. Situated beside the main house, on 2.5 acres surrounded by forest, with easy access to trails. Close to ocean and bay beaches, midway between East Hampton and Sag Harbor. Perfect for a couple with an appreciation for nature!

Location · Comfort · Kitchen

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!

Family · Location · Nearby

Artists Sag Harbor Village Retreat

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. Fully self contained and private. Main Street is lively and all restaurants are open. Central heat with it’s own thermostat controls & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking in driveway close to entrance. Not suitable for infants or children.

Value · Location · Cleanliness

Close to all! Peaceful Heated Pool! *Month

Village Fringe, Close to All, Comfortable 3+ bedroom, 2 Bath log home w/ *Heated pool (*heat option May - Sept). Sun filled.. Located on quiet cul-de-sac close to Ocean Beaches & EH Village! Includes *Pool (Open 5/22 ) w/ outdoor shower & changing area. Relax in teak furniture / hammock after a swim in the 20x40 *pool! Peaceful setting. All amenities one would expect. High speed wireless internet 3 Smart TVs. Monthly Rental Registration # 20-1005.

Family · Location · Hospitality