Holiday rentals with lake access in The Hamptons

Long Island Getaway w/ Heated Pool & Lake

Long term bookings available for Summer 2025! Discounts for longer stays! Heated pool open May-Sep We welcome you to our beautiful home full of history, designed with high end comforts, and filled with activities and amenities. Take advantage of everything Long Island has to offer, situated a short drive away from East End LI- close to NYC, Hamptons, NoFo, beaches, wineries, breweries and more! Relax at home in the heated pool, light a bonfire, play games, and many other activities!

Head of Pond House - Waterfront Cottage

Welcome to the charming, waterfront Cottage at Head of Pond House! Enjoy a peaceful retreat with beautiful lake access year-round and pool access from Memorial Day to October. The cottage features two comfortable king beds, including one in a cozy loft area, a full bath, WiFi, a projector for movie nights, and a fully stocked kitchen. Whether you’re looking for a relaxing escape or a comfortable base to explore the Hamptons, our waterfront cottage is the perfect spot for your getaway.

Waterfront Home with Private Beach

Note: In July and August: our rentals are 7 day periods from Saturday-Saturday starting on 6/29/2024-9/7/2024. in May and June, we have a 3-night minimum. Enjoy your own private beach, fireplace, large deck with amazing sunset views, Kayaks, SUPs, bikes and long summer days on Lake Montauk. Our beach front midcentury house has views from every angle. Swim in the lake or take a short bike ride to Gin Beach. Make fabulous feasts in our chef's kitchen and eat at the large outdoor table.

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.

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 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.

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.

Private paradise 3 min from town ice skating pond!

Located close to everything three minutes from town five minutes from the beaches you have your own pond to ice skate on in the winter months. Home is 2 minutes from Montauk Downs State Park and Golf Course. 5 minutes from Ditch Plains surfing, 8 minute walk to town.