Vacation rentals with lake access in Hampton Bays

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.

2.5 Miles from the 2026 U.S OPEN, Waterfront

Take a break and unwind at this peaceful oasis. Welcome to waterfront living in this beautifully renovated 4 bedroom, 2 bath home situated on .75 acre, adjacent to a marina. You'll be blown away by the unobstructed 180-degree water views over Shinnecock Bay all the way to the inlet. The main feature of this home is the wall-to-wall glass in the living room and dining area, offering panoramic views of the bay. The back two decks are the perfect spots for outdoor dining and relaxation.

Southold Sea'renity

Kick back and enjoy the peaceful surroundings of this beautiful 3-bedroom, 2-bathroom house. Outdoor oasis with hot tub, BBQ, shower, brand new deck & kayaks. Steps away from a fishing lake & 6 houses away from Kenny's beach. This house has been completely remodeled & is perfectly located to fit your getaway needs. Master Bedroom- queen bed, full bath Bedroom 2&3- queen beds Pull out couch and some other extras. Towels, bed sheets, soap, toilet paper, and pillows are included

Hampton Waterview Gorgeous Yard w/Pool /Pizza Oven

-900ft from Shinnecock Bay perfectly between Hampton Bays & Southampton -Access to private bay Beach for boating or paddle boarding! -The home has Mooring rights (you can dock a boat there) -Outdoor propane Patio Heater -Pizza oven & Propane Grill -A bar with metal ice buckets & coolers -One block walk to EdgeWater Restaurant (5 Star Restaurant & Bar) -Huge private backyard with dinner area, chaise and multiple communal chairs locations -Brand New for Summer 23 16x32 Pool !!!

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.

Charming Bungalow on the Bay

This newly remodeled 1960’s bungalow is the perfect getaway for couples and families alike. Located right on Gardiner’s Bay, there’s a gorgeous view of the water from the large windows and front porch. From the front steps you can follow the 300 yard path to your own private beach where you can wade, swim, snorkel, paddleboard, or just enjoy the amazing view and salt air. (East Hampton Rental Registry Certificate Number: 24-234)

Hamptons Waterview Cottage

Nestled between the waterfront and woods in an oasis where nature is everywhere, and the home is a charming cottage style which offers the perfect balance between luxury and rustic. The pool is a shared unite pool with beautiful custom IPE deck on a common waterfront property with a 300' dock. kayaks paddleboards volleyball court ping pong with incredible waterfront sunsets all within 15 minutes of downtown Hampton Bays.

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.

Lovely 2-bedroom apartment in a historic home

Restored apartment in a Victorian home, centrally located in the Village of Greenport. Short, few minutes walk to restaurants, shops, cafes in town. Also, conveniently located (10 minute walk) to the Hampton Jitney bus stop, LI Railroad and Shelter Island Ferry as well as local beaches. Enjoy the charm of a historic home, with all the convenience of modern amenities!

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.

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.

Cozy Cottage on the Great Pond near beach.

In the heart of wine country is the adorable , nautical inspired cottage surrounded by nature, on a beautiful freshwater pond, a quick walk or bike ride away from a beautiful beach on Long Island Sound. Hiking, fishing, wine tours, farmstands abound!