Holiday rentals with lake access in Northwest Harbor

Southampton Modern Barn, Private Hot Tub and Pool

This magical getaway delivers peace and relaxation. Wake up to coffee on your private deck with bucolic views. Play in your heated, saltwater pool, and relax under the stars in your hot tub (open year round). During your stay, these amenities and more will be for your personal use. Stroll to the owner’s dock on Big Fresh Pond, for paddle boarding, kayaking and sunsets. You can also drive 8 minutes to Southampton Village for shopping, restaurants, art galleries and Ocean Beaches.

Duffy's on Lake Montauk

Recently renovated in soft blues and whites, these sleek units offer a full kitchen, washer/dryer, living area and large deck steps from Lake Montauk. Paddle boards, kayaks and beach chairs available in warmer months. All units have Bose players and Roku. The units sit at a 90 degree angle to the lake with partial lake views from the deck. The lake and beachfront are a 1 minute walk from the unit. RENTAL PRICES ALREADY INCLUDE SUFFOLK COUNTY SALES AND OCCUPANCY TAXES.

GREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH

4-6 GUEST MAXIMUM PLEASE. Cozy 2 BR and 1 BTHRM apartment in private home in Greenport NY. Total privacy and separation of unit!! Perfectly situated on 1.75 acres. 3 minute drive, or easy walk, to the center of Greenport village, 2 minute ferry ride to quaint Shelter Island, and a 6 minute drive to tip of Orient. So right in the middle of the action with the peace and serenity of living outside the village. Private beach a short walk/ride down the street.

Waterfront Designer Stay • Sunsets • Near Beach!

Welcome to The Swan House 🦢🏡 —your peaceful, designer retreat on Bellport Bay. Enjoy stunning sunsets, swans gliding by, and direct water access from the backyard. Relax on the spacious deck, fire up the grill, or take a short drive to Smith Point Beach. Inside, you’ll find an open, sun-filled layout with curated furnishings and a calming coastal vibe. This stylish escape offers serene waterfront living in any season—just 90 minutes from NYC.

Bayfront 1BR/2BR detached guesthouse with pool

Perfect relaxing getaway for a couple or family. Bayfront 1BR/2BR fully detached guest house with gorgeous morning views. Property has saltwater pool + hot tub (open May -October) and bay access via private dock. Central to both north & south forks (wineries + Hamptons or Montauk just short drive away). Down the road from famous Shelter Island Sunset Beach + golf course. Come explore the beauty of the Hamptons without the stress!

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.

Waterfront House on Fort Pond, MTK

Spacious house right on Fort Pond with relaxed bohemian vibe. Enjoy the open kitchen, reclaimed wood beams, and hand crafted furniture. Access directly to the water from the back yard. There are two other cottages that are two bedrooms each on property as well. We do live on the property full time and enjoy making our space a safe and clean environment.

Private Suite in a Greenport Historical Townhouse

Enjoy the Greenport experience at this centrally located, renovated Victorian home. Our place is a few minutes walk into town, where there is a flourishing restaurant and food scene. Lots of shops, cafes to explore too and beaches are a 15 minute walk. Take a boat tour of the harbor from nearby Preston's Dock.

Deluxe Studio Apt@The Montauk Manor

Beautiful, deluxe studio apartment with every amenity. Registered historical landmark. Magnificent lobby with fireplace, restaurant. Cable TV with HBO, DVD and WI FI. Great news the in-door pool, jacuzzi and sauna are now open! The restaurant is now open! Don’t miss out on the fabulous beaches.