Vacation rentals in Gardiners Bay

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.

Chic + serene w/ pool~1 block to waterfront dining

Serene, chic, Hamptons oasis! 1 block to waterfront dining + 8 minutes to Main St. + beaches Enjoy your calm, zen, private home nestled in nature + peacefulness. Swim in your pool all day, spark up the firepit + BBQ under the starry sky! Curl up in the living room; cook in the Chef's kitchen + stream on the 80' TV. Enjoy a 1 block stroll to waterfront dining + cafe for coffee on the sea + dinner/drinks watching the sunset over the harbor You'll be 8 mins to Main St., beaches + so much more!

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

Modern Cabin near the Beach

Kick back and relax in this sweet cozy cabin near some favorite local spots in the area. Quick access (under 5 minutes) to Maidstone beach, Rita’s Cantina, Bostwicks on the Harbor, S&S Coffee Shop, Springs Tavern…to name a few. In 10-12 minute drive you can be in East Hampton village or Amagansett Village. The home is set on a half acre in a serene setting in the Lions Head beach association. Walk to private access bay beach from the property. The cabin was renovated top to bottom in 2025.

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

Kenney's Beach Loft - Vineyards, Horton Lighthouse

Kenny’s Beach Loft is a cozy, pet-friendly open-concept queen bed studio with 1 bathroom, a kitchenette, comfortable living and dining area, in-unit washer and dryer, and a private patio. Perfect for families and couples getaway. Just steps from Kenney’s Beach for stunning sunsets and peaceful walks. Minutes to Southold Fish Market, Croteaux Vineyards, Horton Point Lighthouse, and North Fork wineries for dining, wine tasting, and exploring. Enjoy coastal charm, seaside air, and total serenity.

Sunny Daze

This dreamy houseboat rests gently at a family-owned marina, where time seems to slow and nature leans in close. Surrounded by peaceful river views, tall grasses, and birdsong, it’s a floating haven for those seeking calm and creativity. Whether you’re sipping coffee on the deck at sunrise or watching the moon ripple across the water, this riverside retreat invites you to drift, dream, and just be. Enjoy a fire or jump on a paddle board or kayak f or an adventure down the river it has it all!

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.

The Greenport Suite—private entry + near the beach

Welcome to The Greenport Suite! With its separate entrance, secluded outdoor patio space and ideal location, this newly-redesigned private suite in our contemporary Village home is perfect for enjoying a North Fork getaway. We are located just a few short blocks from bay beaches, the harbor, and public transport, while the area's celebrated wineries are a short drive or bike ride away. Come see why Forbes named Greenport one of the 11 prettiest villages in the United States!

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

The Olde Church in Greenport

This one of a kind converted 1867 Church is historic, stylish and close to everything in Greenport, making it easy to plan and enjoy your visit. Located in the heart of Greenport it is walking distance to all restaurants, shops, a local beach, the LIRR and the Jitney stop. This spacious home has maintained some of the most beautiful pieces of the past alongside modern amenities to make your stay memorable and comfortable.

Your Nest Near The Beach

Welcome to A Shore Thing, a retro modern beach cottage. This bright and cheerful escape is perfectly located for exploring the shoreline. Whether you are visiting in the summer for sun, surf and sand or in the quieter off-season, you will find the shoreline is packed with an incredible array of inviting destinations. The cottage is just 3/4 of a mile from the beautiful private sandy beach.