Holiday rentals in Gardiners Bay

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

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.

Serene w/ large pool ~1 block to waterfront dining

Serene, chic Hamptons oasis! Located 1 block to waterfront dining + 8 mins to Main St. A perfect escape for any time of year! During summer, swim all day + walk 1 block to waterfront dining for dinner, drinks, coffee on the sea! During fall/winter, enjoy the firepit, indoor wood burning fireplace, 80' streaming TV + large fully stocked Chef's kitchen! The home is nestled in nature and serenity, perched back on a large piece of private property. Perfect for a serene escape to relax and unwind!

Bay Access Cottage + Pilates Gym

Just a short walk to a quiet bay beach with the most unbelievable sunsets! This charming two bedroom house also boasts a quaint basement gym with a treadmill, Climber, Peloton and Pilates reformer to feel great during your stay. The private fenced in backyard is wonderful for social gatherings with a picnic table and grill to host friends. The outdoor shower on bluestone is a delightful (seasonal) experience. Your private beach access is a 3 minute walk. You will NEVER see a sunset like this one

Light-filled Retreat by the Bay

This light-filled, modern retreat is tucked away in the historic community of Springs, East Hampton. Designed and constructed using only sustainable materials, the home offers a perfect blend of conscious living and luxury comfort.Wake up to birdsong, spend your days lounging by the sun-soaked heated pool, or nights under the stars. The private beach is just a short stroll away. Whether you’re seeking serenity, family fun, or a stylish remote work getaway, this eco-conscious escape delivers.

Hamptons Waterfront Getaway – Stylish & Serene

Waterfront Luxury Retreat in Sag Harbor. As featured in Vogue, Mansion Global, and Homeworthy. This serene designer home offers direct bay access for kayaking and paddle boarding, plus a private path to Clam Island for peaceful walks and beach picnics. Enjoy a gourmet kitchen with Viking and Sub-Zero appliances, spa-like en-suite baths, and plush bedding. Minutes to bay beaches and Sag Harbor village—your private escape awaits. Ideal for romantic getaways, relaxing weeks, or a summer reset.

Oasis backyard, Pool, Gym, and Sunroom!

Oasis pool and landscaping makes it feel like your on a private island. Sunroom with smart TV over looking oasis back yard. Decks in the back yard with lounge chairs and 2 patio dining tables. Front deck with lounge chairs. Outdoor gym located in the corner of the yard. Paddle boards, boogie boards, beach chairs, and beach towels provided. Walk to EHP Resort (SiSi Restaurant), and Harbor Bistro featured on Delicious Destinations. Paddle Diva paddle board/kayak rentals also nearby.

Designer's Dream - Charming Boathouse

An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's with modern updates. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.

3 Min Walk to Beach| 1 Mile to Town | Fam-Friendly

<b>The Greenport Beach Cottage</b> • Bright & updated 800 sq ft coastal cottage • 3 minute walk to beach, 4 minute drive to town • Sleeps up to 5 guests • Family-friendly amenities • Fully fenced in (fence not pictured) backyard with 2 fire pits, charcoal & gas grill, outdoor shower • Garage with 4 beach cruiser bikes, Foosball table & small gym area Book your coastal getaway now- only a few summer weekends remaining! IG: @thegreenportbeachcottage

Sunny, walk to beach, large pool

Walk to the beach from the quiet of the woods! Sunny, contemporary family-friendly house with large pool in the hidden gem of the Northwest Woods section of East Hampton. Walk to Sammy's Beach on the Gardner's Bay, or make a quick drive to the ocean, come home to grill on the large deck and swim in the large heated pool. 40 acres of nature preserve behind you for quiet + unspoiled scenery!

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!

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