Vacation rentals in Wainscott

Serene w/ large pool ~1 block to waterfront dining

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

Family · Location · Hospitality

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.

Value · 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 · Sleep quality

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.

Family · Value · Pool

Beachglass Barn Gated prvt pool King suite 2 baths

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

Family · Location · Bathroom

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 · Value · Decor

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 · Check-in · Hospitality

Luxe|Pool|BeachCar|Games|Movie|HotTub|Firepit

SERENITY AT SHOREWOOD Pool is Open April 1 - November 1. Must be 25+ to book. Luxurious Newly Renovated Mid Century Modern Home in East Hampton with Beach Car! Peaceful and stylish with three bedrooms, 3 1/2 baths, spectacular great room, huge deck, heated pool and more, less than four miles to the heart of East Hampton Village, world renowned for its restaurants, shopping and ocean beaches. A designer-curated architectural gem! Kick back and relax in this calm, stylish space.

Value · Family · Accuracy

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.

Family · Value · Kitchen

East Hampton Secluded Escape with Gunite Pool

Elegantly furnished 4 bedroom house on lushly landscaped grounds, fewer than 5 minutes from the heart of East Hampton Village. This home is ideal for outside living, featuring a gunite, in-ground salt-water pool and stone patio. The interior is bright and spacious, accented by minimalist yet warm furnishings. Common living areas include a large family room with TV, large dining room with gas fireplace, and a large eat in kitchen. Rental registry HMT23-10468

Family · Location · Decor

¤¤¤ Wonderful retreat on 4 acres with pool ¤¤¤

Private, calming, and stylish Hamptons retreat—the ultimate escape from the city. Enjoy an inviting swimming pool from the surrounding hammock, lounge chairs, and swing. The best of indoor-outdoor living is steps away on the wraparound deck featuring an outdoor kitchenette with BBQ, a large outdoor dining table with seating for 12, and an outdoor gas-powered fireplace. All this against the backdrop of 4 acres of private forest greenery.

Family · Location · Backyard

East hampton 3 bedroom home w/ pool great location

Welcome to your hamptons summer home! Amazing location 5 minutes from both Sag Harbor and East Hampton towns and 10 minutes to Bridge Hampton. Beautifully landscaped backyard with heated pool and bbq. The primary bedroom includes a king bed, the 2 secondary bedrooms have queen beds. Open floor plan with kitchen and dining room flowing to the backyard is perfect for indoor/outdoor lunch and dinners. 2 full bathrooms and central air.

Family · Location · Parks