Holiday rentals in Wainscott

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Top-rated holiday rentals in Wainscott

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Guest favourite

Flat in The Hamptons

4.94 out of 5 average rating, 156 reviews

Whaling Captain Pierson's Cottage

Whaling Captain Pierson's Cottage is at a waterfront property. A unique environmental experience, nestled in nature but only a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only cottage offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets and a private low-tide beach. (See my reviews from my other listings entitled, "Whaling Captain Pierson's Apartment" and "Whaling Captain Pierson's Apartment TOO".)

Superhost

Apartment in The Hamptons

4.88 out of 5 average rating, 17 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

Beautiful duplex corner townhouse unit completely renovated in 2021 & in the heart of Bridgehampton Village. 2 min walk to shops, restaurants, main street and a bicycle ride to the beach. Situated all the way at the end of the building it provides ample privacy with Pool open July 4 - Labor Day only. Free parking (2 spots) w/ extra guest parking. Central air conditioning, private patio, ring doorbell/cam, self check in, curated kitchen w/ all supplies. Linens, towels, soap & shamp included

Guest favourite

Home in The Hamptons

4.96 out of 5 average rating, 25 reviews

Fully renovated dream summer house in the Hamptons

This stunning fully renovated and modern appointed summer house is located in a peaceful cul-de-sac on a one acre lot. Ideally located between Sag and E. Hampton, it is only 10 minutes from the Ocean or the Bay. Designed for indoor/outdoor living, you will enjoy its high-end appliances, oversized heated pool and fully equipped deck. The beautiful landscaped garden is completely fenced, private and lit to enjoy late outdoor diners. Your ideal summer oasis to lounge, entertain or rest.

Guest favourite

Cottage in The Hamptons

4.95 out of 5 average rating, 80 reviews

Steps to the Beach - Designer Cove House Cottage

All new modern interior and exterior furnishings by luxury interior designer. Enjoy fabulous water views on the expansive mahogany deck from this sweet beach cottage that was completely renovated and is a short walk to beautiful Long Beach and just a couple of miles to Sag Harbor's Main St. The home features an open floor plan, cozy gas fireplace, an updated kitchen with stainless appliances and Viking range. Three bedrooms (one with a private office) and an outdoor shower.

Top guest favourite

Guest suite in The Hamptons

4.96 out of 5 average rating, 166 reviews

Private king suite 2 bths Private access and pool!

Beautiful, bright, spacious King suite w fireplace, two bathrooms & private separate poolside entrance. We are just minutes to beaches, boating, golf, hiking, biking, yoga and wineries. Play games, grill or cozy up fireside w a good book/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.

Top guest favourite

Home in North Fork

5 out of 5 average rating, 13 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

★ "Beautiful hidden home on the water… enjoy the North Fork summer in style." Private beachfront property with 2 homes & views of Gardiner’s bay. ☞ Bikes + kayaks + paddle boards ☞ Wrap around balcony w/ seating ☞ Fully equipped + stocked kitchen ☞ Deck w/ lounging + water views ☞ Dedicated workspace + printer ☞ Master w/ king + bathroom ☞ 55” Smart TV + Xbox ☞ Indoor gas fireplace 6 mins → DT Greenport (cafes, dining, shopping) 13 mins → Orient Beach State Park ⛱

Superhost

Home in The Hamptons

4.89 out of 5 average rating, 38 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

Superhost

Home in The Hamptons

4.92 out of 5 average rating, 90 reviews

Private Bridgehampton Pool house

Longer stay and reduced rate please email 169bridgehamptoncottage@gmail.com. NOTE* Rest assured, as always, even more so now, our housekeeper is aware to put in the extra tedious clean needed for a happy healthy stay! 7 minute drive to Hampton classic or less 20 min bike ride. Restaurants, studio 89 gym, on same rd. Ocean+bay 5-10 min drive. Bike to 1 ocean Yoga/winery. Halfway to Sag Harbor+Bridgehampton. There is pet fee.

Guest favourite

Villa in The Hamptons

4.97 out of 5 average rating, 31 reviews

SERENITY AT SHOREWOOD 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.

Guest favourite

Home in The Hamptons

4.86 out of 5 average rating, 270 reviews

Exclusive Sag Harbor Compound

A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.

Guest favourite

Home in The Hamptons

4.96 out of 5 average rating, 26 reviews

East Hampton Cottage Oasis

Relax and unwind at our beautiful, private and serene East Hampton Cottage. Our private cottage includes a beautiful backyard and front yard sitting area, light drenched bedroom, and fully equipped kitchen. We are located in East Hampton springs, where you can enjoy the quietness of the Hamptons, but are also close to all landmarks and dining. Everything you need for a short stay, or even an extended comfortable stay!

Guest favourite

Flat in The Hamptons

4.89 out of 5 average rating, 158 reviews

Sag Harbor Village Oasis

Bright and spacious second floor apartment in historic Sag Harbor Village. 10 minute walk to historic Sag Harbor Village Main Street. Five minute walk to Bay beach. Super comfy king bed. Fully self contained with private entrance and hallway. Parking on street close to entrance. Kitchen with stovetop, refrigerator, sink, coffee and tea kettle. No pets - owner is allergic. No infants/children.