Vacation rentals with a fire pit in Cutchogue

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Le Petit Cottage, Southold, NY

Experience the charm of a two-bedroom cottage in Southold, New York. Enjoy easy access to nearby South Harbor Park Beach, where you can swim and soak up the sun. Immerse yourself in the local wine scene with wineries just a short distance away. Explore nearby farms to savor fresh produce and artisanal goods. Unwind on the outdoor deck in the fresh North Fork air after a day of swimming, wine tasting and farm visits. Greenport and Shelter Island Ferry are a short ten minute drive away.

Renovated 2-Bedroom Cottage on the North Fork

Serenity awaits as you step into this totally renovated Cottage. The property is perfectly located in the heart of Long Island's Wine Country. Centered on the North Fork this home allows you to explore all that there is to offer…. antique shops, restaurants, vineyards, breweries, farm stands and the beautiful Causeway Beach is just steps from this home. The home is newly renovated with a new kitchen, appliances, new bathroom, outdoor gas grill, fire pit and a beautiful screened in porch.

Summer Retreat at the beach , enjoy Wine Country

* We provide a Beach Parking Pass for all Southold Town Beaches * 10 min walk to neighborhood sandy beach! * 5 min walk to vineyard with tasting room. Spacious Contemporary home. Master Bedroom plus 2 more bedrooms and 2 bathrooms on the second floor. Living room & kitchen on main floor. Wake up to beautiful garden view. Large kitchen and dining area for the whole family. Just minutes from Long Island's wineries and wedding venues. This home comes complete with everything you need!

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

[FOLLOW US on INSTA @29watersedge] 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.

Enjoy a relaxing getaway to the North Fork

One bedroom suite, with separate entrance in quiet Nassau Point; a peninsula, surrounded by beaches. Nassau Point is a great place to bike, walk and enjoy nature. Fully functioning WiFI for guests looking to extend their stay, while working from home. Fishermen's beach is a 5 minute walk Causeway beach is a 10 minute walk with parking. Point beach, 1.5 mile walk, a Southold Parking Permit required. You will find 20 wineries within 5 miles, just a short Uber ride away.

Modern Farmhouse Steps to Beach & Love Lane

Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

Stunning waterfront modern farmhouse with dock.

Relax with the whole family or a group of friends at this peaceful, waterfront cottage. Perfect spot to bring a group for a country retreat in the heart of stunning vineyards, spectacular restaurants and stunning waterscapes. Our home’s interior is beautifully appointed where you will be comfortable both inside and outside on our patio, or deck with a breathtaking waterfront view. Peaceful, relaxing and magical place in an idyllic spot.

Beach Barn w/ Heated Pool & Sauna - Dog Friendly

@WaterMillBeachBarn Dog friendly (upon approval) Hampton Beach Barn with pool and infrared sauna. POOL OPEN - May 1st - October 23, 2026 This impressive house, nestled within a rustic, woodland plot, promises a tranquil stay. Eclectic designer decor is complemented by striking rustic touches, such as Dutch-style farm doors, exposed beams, and vintage wood-burning stove.

Cozy Seaside Cottage

The Cottage at Whitecap is part of an Historic Compound built in 1883 and is located in the heart of New Suffolk. The Cottage offers 4 Bedrooms and 2 Bathrooms. The house is steps from the beach and conveniently located by restaurants, wineries and a public boat ramp. It's the perfect location for your next vacation, small get together or winery weekend getaway.

Walk to Breakwater Beach in Heart of Wine Country

Private and peaceful cottage walking distance to Breakwater Beach and Old Mill Inn Restaurant on the water opening Spring 2025. There are two large decks to relax by the firepit and drink your wine from the local wineries. Bikes, kayak, and paddle board are stored in the barn for guests use. Easy access to the marina, fishing, fine dining, vineyards, and farm stands.

Secluded Farmhouse - Studio Apartment Style Unit

Private studio suite with separate entrance and full bath in a modern North Fork farmhouse on a peaceful farm property. Enjoy a screened porch, fire pit, and outdoor seating. Includes mini fridge, Keurig, tea, homemade granola, and seasonal eggs/produce. Attached to our home, so some light household noise is possible. Private chef + yoga services available.