Holiday rentals in Gardiners Bay

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Top-rated holiday rentals in Gardiners Bay

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Top guest favourite

Home in East Hampton

4.95 out of 5 average rating, 235 reviews

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.

Guest favourite

Home in East Hampton

4.95 out of 5 average rating, 439 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 late check-out are NOT available in season

Superhost

Home in East Hampton

4.87 out of 5 average rating, 209 reviews

HeatedSaltWaterPool, Walk2Beach, FencedYard4Pet

Meticulously cleaned home.Tranquil family neighborhood in historic artist's beach community.Heated saltwater pool.Wood burning fireplace.Private fenced-in backyard.Half mile to private bay beach. Bike great trails & savor delicious meals prepared in fully equipped kitchen.Enjoy Clearwater Beach's renowned sunset. Easy living home.We welcome all respectful guests.East Hampton's best restaurants are nearby.Smoke free.Small dogs permitted.Cell reception booster! Ask about EVcharger.RentalR-25-705

Top guest favourite

Cottage in Greenport

5 out of 5 average rating, 20 reviews

3 Min Walk to Beach| 1 mi to Town |Baby&Beach Gear

Welcome to The Greenport Beach Cottage — a coastal retreat nestled in a quiet beach community just minutes from the action of downtown Greenport. This newly renovated 750 sq ft beach cottage is a short 3 minute walk to Gull Pond Beach and a 4 minute drive to downtown Greenport. The stunning clifftop Kontokosta winery is a quick 3 minute drive away. Add us to your wishlist by clicking the ♡ in the upper-right corner. Book now —only a few summer dates remaining!

Superhost

Flat in East Hampton

5 out of 5 average rating, 4 reviews

The Hideaway | Clearwater Beach

Your private retreat in the heart of Clearwater Beach, East Hampton! Escape to this serene, design-forward suite nestled in one of the most peaceful corners of the Hamptons. Just minutes from the bay, this luxury hideaway offers the perfect balance of comfort, style and convenience. The space features a plush king bed and all the amenities you need for a relaxing stay. Sip your morning coffee in your private outdoor space before heading off for a swim at Clearwater Beach.

Top guest favourite

Home in Greenport

4.98 out of 5 average rating, 226 reviews

Aqua Vista

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).

Guest favourite

Home in Greenport

4.93 out of 5 average rating, 115 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

Top guest favourite

Guest house in Shelter Island

5 out of 5 average rating, 65 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!

Guest favourite

Villa in East Hampton

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.

Superhost

Home in Orient

4.82 out of 5 average rating, 66 reviews

Corner 3BR Home - Private Beach!

We offer boat cruises around the east end of long island, reach out for more information 1,100 Square Foot house with 400 square foot deck in the backyard, along with am outdoor sofa lounge (fire pit in the fall and winter) lounge under a shaded pergola and an outdoor hot shower. House is part of community with rights to a private beach with a private barbecue/recreation area only a few minutes walk away. 14nt.min

Top guest favourite

Flat in Greenport

4.96 out of 5 average rating, 96 reviews

Lovely 2-bedroom apartment in a historic home

Restored apartment in a Victorian home, centrally located in the Village of Greenport. Short, few minutes walk to restaurants, shops, cafes in town. Also, conveniently located (10 minute walk) to the Hampton Jitney bus stop, LI Railroad and Shelter Island Ferry as well as local beaches. Enjoy the charm of a historic home, with all the convenience of modern amenities!

Guest favourite

Flat in Shelter Island Heights

4.91 out of 5 average rating, 250 reviews

Squire Chase House

Wide open loft like space in the heart of the Heights walking distance to North ferry and Marie Eiffel market Many antiques including 1930s leather club chairs and a wonderful 1850 Swedish gustavian sofa in the living room many original pieces of art work Note :the bath tub in the master bedroom is for decoration only Shelter Island license B Zone