Beach house holiday rentals in Greenport

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.

The North Star: Greenport Waterview Beach Getaway

Welcome to our charming home in Greenport, NY. Right across the street from the private community beach! We are neighbors to the most famous wineries on the North Fork. 3 bedrooms, 2 baths, & a den that has a pull-out queen sleeper sofa. Private beach. Outdoor shower. Comes fully equipped with towels & linens. 2 miles from the town of Greenport. Perfect house for families/groups. DOG(s) FRIENDLY (w/ a pet fee) with fenced front yard & deck- sorry no cats! Looking for adults aged 30 or over.

North Fork Waterfront Log Cabin

Step back into simpler times in this spectacular newly remodeled waterfront log cabin right in the heart of the North Fork. Spend your summer days cooling off in the water and nights sipping wine by the fire or exploring the endless local family farms, vineyards and dining nearby. This quiet & secluded cabin sits right on James Creek estuary within the Peconic Bay. Enjoy swimming, fishing, kayaking and paddle boarding off your own private dock or just simply watching the scallop boats go by.

North Fork True Beachfront Home

This is New York version of California's Big Sur, with direct beach access and spectacular water views, surrounded by forest. Modern, 3,000 sq feet. Walk down path from house to a fantastic sand beach with lifeguard. Large deck for lounging, BBQ, and sunset views. 4 bedrooms, 3 baths, outdoor shower, 4 person hot tub, 2 person sauna, separate den w/home theater, gym, hammocks, wood burning fireplace. Experience the Long Island Sound without neighbors and the suburbs; a naturalist's haven.

Hamptons Beach House- Sun, Sand & Relax-Beachfront

This beautiful Hamptons beachfront home is right on Shinnecock bay with your own sandy beach right in the backyard! Relax with your toes in the sand or go for a swim. Located just 4 min. by car from the main town for all your shopping needs. My place is also within walking distance to one of the Hamptons best waterfront restaurants- so no worries about having a drink and getting home. The location and ambiance is what makes my place stand out from the rest. You’re gonna love it here!

Coastal Cottage on the Water

A coastal cottage on the water surrounded by vineyards and farm stands on the North Fork. Unwind in the backyard with a private view of the Goldsmith's Inlet where you can watch the sunrise, bird watch, and admire our local swans. A quick 5-minute walk to the Long Island Sound where you can sunbathe, swim, kayak, and watch the beautiful sunset. Conveniently located near Greenport, Orient, and Southold. *IMPORTANT* Kayaks and grill are only available from May 1st to October 31st.

Hang by the (Chel)SEA

Enjoy a relaxing stay with family and friends at this cozy soundview beach house. Wake up to breathtaking views of the water, where you can go right into the back yard of your very own private beach! Have a morning coffee on the front balcony of the home that overlooks the beautiful marshlands and then spend the day relaxing on the beach, or kayaking in the water! End the evening with a glass of wine on the back deck, that overlooks the water with the most spectacular sunsets!

East Hampton Beach House · Heated Pool

Tucked away on a quiet street just two blocks from Clearwater Beach, this modern bungalow offers the perfect coastal escape. The bright, open layout features 3 bedrooms, 2 baths, a sleek kitchen, dining area, and a spacious lounge filled with natural light. Four glass sliders open to a large deck with lush landscaping and a private 18x45 heated pool—your own backyard oasis. Enjoy summer living just a short walk to Clearwater Beach, a lovely bay beach club.

Stunning Bay-front Views - Hampton Bays

Enjoy stunning bay views from sunrise to sunset at this picturesque, Nantucket style beach home located in Red Cedar Point. This spacious bay front home features 6 bedrooms, 4 bathrooms, large open living room, eat-in-kitchen, dining area and den. Outdoors enjoy sitting on the patio, overlooking the bay views, a soak in the Jacuzzi, or swim in the bay. Ideal summer getaway, moments from restaurants and ocean beaches.

NoFo Getaway: Pool, Farm Views, Beach Sunsets

Our family friendly home is set on a spacious green parcel, abutting a farm and the ocean with a pool, outdoor shower, large deck, stone firepit, pool shed, children's custom built playground, lawn games and more. Central air is installed throughout. The home features 4 bedrooms, 3 full bathrooms, 1 half bathroom and an outdoor shower. FOR VIRTUAL TOUR OR VIDEO TOUR PLEASE EMAIL AND WE WILL PROVIDE

North Fork Waterfront Escape · Sunset Views

Enjoy spectacular views of Hashamomuck Inlet off Shelter Bay from the living room, kitchen, deck, garden, and private dock of this newly renovated 3-bedroom home. With 90 feet of waterfront and a small sandy beach, it's ideal for kayaking, clamming, and swimming — perfect for families with young children. Relax with sunsets, barbecues, and local North Fork wine. The perfect family getaway!

Charming, waterfront beach house

Step back in time staying at this 1950s cottage right on Southold Bay. You will be hard pushed to find views and a setting more stunning than this house. If you like charm, cozy and vintage this house is your dream! I will let the photos speak for themselves but please feel free to get in touch with any questions you might have * ONE MONTH MINIMUM IN SUMMER