Vacation rentals with a kayak in Berkshire County

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Top-rated kayak rentals in Berkshire County

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Guest favorite

Cottage in Becket

4.94 out of 5 average rating, 159 reviews

The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit • Canoe & 2 kayaks • 50" smart TV and 4 Google Smart Speakers • 1 Gigabit Wi-Fi 'gorgeous with amazing views' • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

Guest favorite

Home in Becket

4.93 out of 5 average rating, 130 reviews

Lake front retreat - Stylish Berkshire home

Drive down a lovely country wooded road to this renovated 4 bedroom mid century home on Long Bow Lake. The house has wood floors throughout & hip design. Gas fireplace in the dining room. This will be a home for the family to enjoy. We have our own private lake frontage that includes a dock & 4 kayaks. Enjoy the screened in porch, Weber gas grill, ping pong table & games. The area is quiet & peaceful only 20 minutes from Downtown Lee, Outlets, fabulous hikes & minutes from skiing Otis Ridge.

Guest favorite

Home in Great Barrington

4.96 out of 5 average rating, 150 reviews

Elegant Year-Round Lakeside Retreat with AC

The Haven, an elegant cottage surrounded by woods, located on a pristine lake with private dock. 4 bedrooms, 3 baths. This year-round vacation cottage with hot tub provides an experience in the Berkshires you won’t forget! Leaf-peep in fall, ski in winter, hike in spring, kayak & swim in summer, or browse the boutique shops in quaint towns like Great Barrington, Lenox and Stockbridge. Newly installed mini-splits provide AC in all bedrooms and LVR/DR/Kitchen common area. 1 house-trained dog ok.

Guest favorite

Cabin in Stockbridge

5 out of 5 average rating, 18 reviews

Lakeshore cabin with private beach and dock

A classic Berkshire cabin nestled under maple trees, on the shore of the Stockbridge Bowl cove. Serene, peaceful and private, yet close to all area attractions. Newly renovated. Large light-filled living room with cathedral ceiling and skylights. Main bedroom on ground floor with bathroom. Enclosed porch and large deck with gas grill. Swimming and kayaking off the dock. Large lawn with lots of trees. Forest trail and waterfall next door. Plenty of parking. 5 minutes to Tanglewood and Kripalu.

Guest favorite

Cottage in Hinsdale

4.99 out of 5 average rating, 150 reviews

Cozy Cottage in the Berkshires

Come and enjoy our "happy place" year round! Our cozy, neat as a pin cottage is located in the beautiful Berkshires with gorgeous Ashmere lake views, spectacular flower beds and beach/lake access. Summer, fall, winter or spring, the cottage welcomes you, complete with a gift basket and fresh flowers. Enjoy the view of the lake off the spacious deck or play games in the grassy yard complete with fire pit for roasting marshmallows. Waterfront is only a minute or two walking distance away.

Guest favorite

Rental unit in Canaan

4.97 out of 5 average rating, 115 reviews

Queechy Lake Carriage House

Comfortable, two bedroom 2nd floor apartment, fully equipped kitchen, well-lit open living space, a short walk to our dock with kayaks and canoe, our association’s beach, playing fields & pavilion. Sits over a garage space which houses bicycles & outdoor games such as croquet, beach toys, and life vests for guest use. Close to endless museums, historical sites, music & art venues, hiking trails, skiing, restaurants, breweries, wineries in Columbia County NY & Berkshire County MA.

Guest favorite

Cabin in Monterey

4.95 out of 5 average rating, 263 reviews

Amazing Berkshire Mountains Cabin

Our incredible 4 bedroom home is situated on 2 beautiful secluded acres in picture perfect Monterey - the ultimate Berkshire County getaway, with modern kitchen, screened porch, 2 fireplaces a fabulous outdoor hot tub and a beautiful brook on the property. Enjoy hiking the Appalachian Trail in nearby Beartown State Forest or kayaking and swimming in the incomparable Lake Garfield. We are a quick ride to Ski Butternut, Catamount, Tanglewood, Lenox and Great Barrington.

Guest favorite

Home in Great Barrington

5 out of 5 average rating, 42 reviews

The Yellow Victorian With Chefs Kitchen

Tender Heart Sanctuary- for slow living, good food and good people. An 1887 house remodeled in 1991, blending the old with the new in the heart of Southern Berkshire County. A space for activity! Perfectly located to be close to everything around to enjoy The Berkshires but also, big and comfortable enough to stay at home. Play chef in the kitchen, enjoy a good tub soak, small library, movies, games. Also a park next door, trails, hike, bakery and tea store.

Guest favorite

Home in Adams

4.91 out of 5 average rating, 101 reviews

Beautiful Victorian. The heart of the Berkshires.

The whole group will enjoy easy access to everything from this centrally located place. The house has been completely renovated. The side patio has plenty of room for a large group with a brand new Weber grill and propane fire pit. Enjoy morning coffee on the front porch. Just steps from the Ashuwillicook Rail Trail. Greylock Glen is less than a half mile away with hiking trails. Mass MoCA is 5 miles away. This Victorian beauty is cozy, warm, and inviting.

Guest favorite

Home in Becket

4.98 out of 5 average rating, 43 reviews

Lakefront in the Berkshires

A winter wonderland! This lake house is just as good in the winter as it is in the summer. Imagine looking out the many windows overlooking the lake and distant mountain while sitting in front of a huge wood burning stove. A direct lake front cottage on a private point. The screened in porch is only 50 feet from waters edge. The fire pit is perfectly angled to enjoy the westerly sunsets. Large grocery store, shopping and restaurants 9 mins away.

Guest favorite

Home in Otis

4.98 out of 5 average rating, 98 reviews

Direct Lakefront Home on Otis Reservoir Giant Yard

Year round retreat directly on Otis Reservoir offering 62’ of lake frontage on MA largest and fully recreational lake. Enjoy the lake views right from our docks, firepit, expansive deck, main floor or bedrooms. The house sits 100 yards back from the lake leaving a large lawn for outdoor activities. Updated and renovated in 2021! Many local snowmobile trails and ski resorts too! Heated garage and 2nd driveway for larger trucks/trailer or RV's.

Guest favorite

Cottage in Canaan

4.9 out of 5 average rating, 131 reviews

Plan your Berkshires by the lake

Very comfortable three-bedroom cottage in a quiet, private association on Queechy Lake. Perfect for families. Hi-speed Spectrum internet, AllClad cookware, electric range, microwave, sharp knives, coffee maker, charcoal BBQ, and tons of places to hike. Apple TV and a Bose Bluetooth soundbar. There’s a large Solo Stove firepit as well as 2 kayaks and a paddle board for tooling around the lake. Close to supermarkets. 15 minutes to Tanglewood!