Waterfront holiday rentals in The Berkshires

Waterfront Gem: 1BR w/Private Balcony & Serenity

Escape to our waterfront serenity in this cozy 1-bedroom haven! Wake up to dazzling sunrises dancing over the water, and end your day with unforgettable sunsets painting the sky from your private vantage point. This is more than just an Airbnb; it's an experience for the soul. Sip your morning coffee on the deck, enveloped by the fresh scent of the water and the melody of birdsong or spending cozy evenings by the fire pit. Book your stay and let the magic of the waterfront work its charm on you!

River Cottage

Beautiful cottage in the Adirondack Mountains situated on over an acre of waterfront property with River access. Enjoy swimming, Kayaking and fishing on the Hudson River, all right from the backyard of the house. It has a great deck which overlooks the river with perfect views for enjoying sunset cocktails… Yard also has two fire-pits for night time fun and laughs. Cabin is close to skiing, snowmobiling trails. Perfect for a family getaway to make awesome memories. STAY, SPLASH, SMORES!!!!!

Seaside Summer Escape: 2BR Waterfront Condo w/Pool

Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on a private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

Bantam Lake Waterfront Retreat with Private Beach

Waterfront home on Bantam Lake, 3BR/2BA. Relax on the deck, enjoy the sunrise, swim at your private beach. Kayaks available for use (4); bring your boat or jet ski. Minutes away from hiking, snow skiing, vineyards, biking, and so much more. The area offers great restaurants and family friendly activities that are minutes away. BBQ on the gas grill, enjoy the fire pit on the beach. House is great for couples, individuals & families. Please check first if you plan to bring a boat. 7 maximum.

Brand New Direct Lakefront - Panoramic Sunsets

Completely remodeled lakefront apartment offering sweeping views of Pattagansett Lake. Open floor plan, fully equipped kitchen and massive deck make for an ideal gathering place to catch up with family or friends. All three spacious bedrooms offer comfy queen memory foam mattresses, fresh linens and UHD smart TVs. Two full bathrooms, high speed internet and in-unit laundry. Picturesque natural setting yet close to town amenities, restaurants, beaches, casino and area attractions.

Waterside Log Cabin on Lake George- Panoramic View

One of the best views of Lake George. 1940s classic log cabin situated 35 ft from the shores, between The Boathouse Restaurant and Lodges and Tea Island Resort (Exit 22 off Northway). Beautiful, private home with panoramic view of one of North America's most pristine lakes. 5 min drive to Lake George Village and 10 min drive to Bolton Landing. 22 ft dock with swim area & floating dock. Relax and watch the sun and moon rise off our deck from this quaint get-away destination.

Charming Lakefront cottage with beautiful views

Make memories with family or friends at our perfectly situated waterfront getaway. Enjoy the tranquility of waking up to peaceful mornings with a cup of coffee on your bedroom balcony. Take a leisurely tour of the lake in our kayaks or paddleboat. In the evenings, enjoy toasting smores on the camp fire. Our spacious dock is great for fishing or sitting in the Adirondack chairs with your favorite beverage. We look forward to offering our guests a vacation to remember.

Sunset Bay: Amazing waterfront w/ dock on 5 acres!

SUMMER 2025 FULL/FALL OPEN Amazing waterfront property on 5 acres with west-facing sunsets overlooking the water & mountains. Private. Two-tiered deck, stone patio, & hot tub, open floor plan living/dining/kitchen. Private dock to swim off of and/or dock your own boat (May-Sept). Includes attached apartment with bedroom, kitchen, bathroom, and living room. Most bedrooms can flex to be King beds or split to make twins. Be close to everything yet away from it all.

Cozy Waterfront Retreat

Serene waterfront retreat! Direct waterfront property on Oyster River perfect for kayaking, fishing, paddle boarding or just soaking up the sun. This cozy cottage with views of stunning sunsets allows guests to relax and unwind. Minutes to local restaurants and shopping, walking/bicycling distance to the towns best beaches; close to outlets and casinos. Quaint, charming cottage with beach decor throughout.