Cottage vacation rentals in Hampton Bays

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Top-rated cottage rentals in Hampton Bays

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Guest favorite

Cottage in North Fork

4.97 out of 5 average rating, 151 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.

Guest favorite

A cozy living area is presented with a green sofa and accent chair, complemented by a white coffee table. Light streams in through windows adorned with sheer curtains. A staircase leads to the loft area, while nautical-themed decor adds charm to the space.

Cottage in Westhampton Beach

4.93 out of 5 average rating, 164 reviews

Cool Tiny Cottage Artist Loft!

He Loved All Things Sea & I Followed Suit. 38 Years Ago My Father Built This Very Special Artist Loft Cottage Retreat. This Tiny Home is One Of A Kind. Throughout The Years Guests & Family Have Come & Gone Creating Beautiful Memories. The Space Is Tranquil, Serene, Peaceful & Harmonious. It’s A Wonderful Romantic Space, Charming For Family Gatherings, or One For A Soul Heart In Transition. All Have Found Passion, Peace and Progress Here. The Cottage Boasts A Fully Fenced In Large Yard, Deck, Grill, Light & Airy Vaulted Ceiling In Living Room With A Chenille Slip Cover Queen Sleeper and Cool Lounger With Library Bookcase With Books And Stereo/CD/Cassette, Color TV & DVD. Staircase to Loft Full Bed & Cute Twin Bed Area. Very Clean & Decorated Adorably. Wifi. Linens & Kitchen equipped, Washer/Dryer. Dining Table for 4 W/Sliders to Deck. Outside Seating for 6 & A Gas Grill. Perfect Place for 2. Quiet At End Of St. 1.5 miles to Rogers Beach Dune Rd/Ocean. 1 Mile To Main Street Village. 15 min to North Fork Wineries & Farms. Agent owned.

Guest favorite

A long wooden boardwalk winds gently towards the horizon, flanked by a railing that provides a clear view of the serene beach and distant island. The bright blue sky, dotted with wispy clouds, enhances the coastal atmosphere of the setting.

Cottage in Milford

4.95 out of 5 average rating, 99 reviews

SILVER SANDS BEACH COTTAGE MILFORD NEAR YALE/TRAIN

Classic 1920s beach cottage perfect for your summer at the shore! It is tucked away on a quiet street, across from Silver Sands Beach Milford. This cozy cottage offers 2 bedrooms with bonus loft sleeping area. In one of CT's most desired shoreline locations, steps to the private beach & Silver Sands State Park boardwalk, walnut beach, ice cream and cafe. Close to downtown green which offers bars and restaurants, train to NYC and New Haven, Yacht Clubs and Yale. Beach Vacation. Pet Friendly!

Guest favorite

A gravel driveway curves through a manicured green lawn, surrounded by tall trees. A black car is parked to the side, indicating convenient parking. The scene suggests a quiet outdoor environment, enhancing the feeling of seclusion and tranquility.

Cottage in Southampton

4.96 out of 5 average rating, 133 reviews

Charming Southampton Light filled Cottage

Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

Top guest favorite

Cottage in Fairfield

4.97 out of 5 average rating, 119 reviews

Charming Fairfield Beach 3BR Cottage By The Sea

Charming Beach Cottage – Steps from Private Beach! Welcome to our newly renovated seaside retreat—a perfect getaway for families, couples, or anyone looking to relax by the shore. Nestled just steps from a private beach (right across the street!), our charming cottage offers the ideal balance of coastal tranquility and convenient access to town. Whether you enjoy walking, biking, swimming, fishing, kayaking, or simply napping in a shady hammock, this is the place for you.

Top guest favorite

A scenic view of a sandy beach stretches alongside calm waters beneath a bright blue sky dotted with fluffy white clouds. Gentle waves lap at the shore, while grassy dunes and rocky formations add natural texture to the landscape.

Cottage in Waterford

4.99 out of 5 average rating, 142 reviews

Coastal Cottage Private Studio

Beautiful coastal studio cottage located on the shoreline of CT. Your cottage is spacious and private with keyless entry and private dedicated parking. Originally an art studio, this recently renovated cottage is one mile to the beaches and local attractions. Our cottage is popular among Connecticut College, Coast Guard Alumni/parents and for anniversary celebrations! Enjoy...Now you can kick back and relax... you've found your home away from home! 🤩🏡 😊

Guest favorite

Cottage in Montauk

4.87 out of 5 average rating, 100 reviews

Secluded 1Br cottage on the lake, close to Ditch

This is the best of Montauk living, right by the lake, close to Ditch, and with an incredible, lush front yard suitable for outside dining or having a couple friends over for dinner. Walk down to the lake to enjoy the sunset, or stroll over to the Crow's Nest for drinks or dinner. No need to drive, it's well within walking distance. Join the many that have experienced the magic of our cottage at South Lake.

Top guest favorite

A bright bedroom features a spacious bed with white linens and a navy throw blanket. Large windows provide unobstructed views of the water and surrounding landscape. A framed photo is visible on the wall, adding a personal touch to the serene environment.

Cottage in Montauk

4.88 out of 5 average rating, 239 reviews

Waterfront Cottage, Fort Pond MTK

Perfect cottage perched above Fort Pond with epic views and relaxed bohemian vibes. The cottage is private with a private deck on shared grounds with a fire pit, hammocks, paddle boards, kayak, and lake access. The grounds are expertly landscaped and take full advantage of fort pond views. We do live on the property full time and enjoy making our space a safe and clean environment.

Superhost

The open kitchen and dining area feature warm wooden flooring and cabinetry. A central island with bar stools provides seating, while a dining table is positioned by large windows, allowing natural light to brighten the space. Appliances are neatly arranged, enhancing functionality.

Cottage in Sag Harbor

4.87 out of 5 average rating, 103 reviews

Secluded Hamptons Cottage

This cottage has high ceilings, is bright and airy, has a wrap around deck with a great overhang for hanging out in the shade or sun. You can not see a neighbor. It has been described as “an adult tree house.” Just a fun and relaxing place to be. It is on over an acre of rustic property. Perfect for watching wildlife.