Vacation rentals with a kayak in The Berkshires

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in The Berkshires

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

Home in Glen Spey

4.99 out of 5 average rating, 135 reviews

Lakehouse Getaway/Winter/Summer/Spring/Fall

Book this lakeside retreat as a romantic getaway, family vacation, or family reunion, with our sister property. Imagine, beautiful scenery, fresh air, breathtaking views, all while relaxing in our lakefront Gazebo, Our spectacular seven person Hot Spring Spa, or optional (extra charge) Bimini Top speedboat. When not spending time on the 2 acres... feels like 20 since it borders open forest, you can visit Bethel Woods, ResortsWorld Casino, Forestburgh Playhouse,fine dining etc all within 20 min!!

Guest favorite

Home in White Lake

4.84 out of 5 average rating, 37 reviews

Waterfront Getaway with a MotorBoat

Experience a unique getaway at our charming double decker boathouse on serene White Lake. Ideal for couples or small groups, unwind in a cozy space with stunning lake views, private dock access, and modern amenities including kayaks and optional boat rental. Savor al fresco dining in our vine-covered patio, and create unforgettable memories in our waterfront haven. Immerse yourself in the magic of lakeside living! Enjoy a lavish, upscale vacation in our fully stocked home. Pets are welcome!

Top guest favorite

A spacious deck overlooks the serene lake, surrounded by lush trees. Comfortable seating arrangements, featuring teal cushions, are positioned around a glass-topped table. Potted flowers add a splash of color, enhancing the tranquil outdoor setting.

Cabin in Sussex

4.96 out of 5 average rating, 228 reviews

Cozy Lake Cabin Spectacular Views Beach Boat Swim

Indulge in a truly breathtaking getaway. Nestled in a serene location with stunning lake views in Vernon Twp, NJ. Ski Mountain Creek or Mount Peter visit Crystal Springs & Warwick, NY. Luxury & comfort, prepare to be pampered. Fully stocked chef's kitchen, themed bedrooms,"Ski Room & Canoe Room". Stone shower, cozy cabin boast carefully curated decor & beautiful lighting a soothing ambiance at a cottage dreamhouse. A chalet vibe to rejuvente as you bask in the warm glow of the stone fireplace.

Top guest favorite

A modern cabin in a secluded setting is depicted, featuring a red exterior and a sloped roof. The cabin is positioned near a serene body of water, surrounded by vibrant autumn foliage reflecting in the water. A clear blue sky adds to the tranquil atmosphere.

Cabin in Stoddard

4.97 out of 5 average rating, 157 reviews

Secluded Renovated Retreat Surrounded by Nature

Get away from it all in a secluded, yet modern cabin, which guests have loved for its "silence and beauty" and called "peaceful" and "serene". Located on the Lakefalls Estate, which maintains the roads, Mended Oar features heated floors throughout, a well-furnished kitchen with quality appliances and equipment, and luxurious linens. Hike the many trails outside the door on the snowshoes you'll find, then come inside to enjoy the wood burning fireplace (wood provided) and play a board game.

Top guest favorite

Cottage in Southwick

4.98 out of 5 average rating, 104 reviews

4 Kayaks Fire Pit & Lake Views from Hot Tub

Congamond House is the perfect lake home getaway. Kayak the calm North Pond. Get your breathtaking pics of the surrounding wildlife. Cuddle up on the deck and enjoy the stars or relax in the hot tub under the deck while gazing upon the lake. This 1500 sq ft cottage is the perfect size for 2 families. (4 adults w/4 kids or 6 adults) Minutes from Six Flags Amusement Park, the Big E and the Basketball Hall of Fame 4 Kayaks that seat 6. Paddles and life vests provided 20 min. from Bradley Airport

Guest favorite

A welcoming exterior of a cabin is shown, featuring a light gray façade with a sloped roof and large arched window. A railing borders the porch that provides river views. Lush green grass and autumn foliage frame the scene, enhancing the tranquil riverside setting.

Cottage in Clifton Park

4.83 out of 5 average rating, 92 reviews

Waterfront cabin 9 - Kayaks - 24 mins to Toga

Watch the boats pass by as you enjoy the views from this stylish riverfront camp in the heart of the Capital District. Towpath Landing is a collection of 18 waterfront cabins that I am bringing back to life. Cabin Bleu has expansive views of the Erie Canal/Mohawk River, fully stocked kitchen with granite, huge front porch with table, grill and relaxing chairs PLUS a screened in back porch for relaxing with a woods view. This is served by filtered river water so bring drinking water.

Top guest favorite

The welcoming exterior of a two-story home is surrounded by lush trees and greenery. A flag is displayed prominently on the front porch, which is bordered by a pathway leading to a deck visible in the background.

Home in Hadley

4.97 out of 5 average rating, 30 reviews

Adirondack retreat!

Relax with the whole family at this peaceful place to stay. Large back yard with a fire pit, deck for entertaining, truly a home away from home. Take the golf cart down to the lake, where you can float around, enjoy the paddle board, canoe and kayak. Majestic Marina is .25 of a mile away, where you can place a boat, or even rent one. Rafting in Lake Luzurne, and the home is close to Saratoga and also Lake George. Ledgerock Winery is close by and some fun bars and restaurants too!

Top guest favorite

A waterfront property is positioned on a hillside, with a tiered landscape leading to a private dock. The building features multiple decks and large windows, offering unobstructed views of the surrounding nature. Green lawn and rocky pathways create a welcoming outdoor space.

Home in Queensbury

4.99 out of 5 average rating, 169 reviews

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.

Guest favorite

Home in Otis

4.96 out of 5 average rating, 108 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, Solo Stove 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

A cozy cabin is nestled among tall trees, featuring dark wooden siding with orange accents. A small porch is visible, furnished with two white chairs. A stack of firewood is arranged nearby, and a short flight of stairs leads up to the entrance.

Cabin in Hadley

4.91 out of 5 average rating, 11 reviews

Great Sacandaga lake retreat

The perfect couples retreat. Take it easy at this unique and tranquil getaway. Relax in this cozy cabin in privacy. Enjoy morning coffe on the front covered deck with views of the Great Sacandaga Lake. Take advantage of the kayaks on site with access to the 84' of direct waterfront across the street. There is a grill on the front deck and on the water front for your use. Dock is also available. 30 minute drive to historic Saratoga Race Track.

Guest favorite

A private campsite is surrounded by lush greenery with a view of the water. A safari-style tent and deck are positioned among trees, complemented by a seating area and a hammock. Sunlight filters through leaves, enhancing the natural setting.

Campsite in Lake Katrine

4.96 out of 5 average rating, 169 reviews

Private Waterfront Winter Camping Experience

**WATER IS NOW ON FOR THE 2025 SEASON! Owner operated private single campsite! This quaint little tent and private deck are nestled among the trees on the banks of the Esopus Creek in a great little neighborhood! A way to get back to nature without truly leaving it all behind. A one of a kind private waterfront escape with a fire pit & electric! WATER ACCESS AND KAYAKS NOW AVAILABLE! Enjoy a 2.5 mile stretch of the Esopus creek!

Top guest favorite

A private waterfront area is shown with clear, calm river water lapping against a pebbled shore. A pontoon boat is moored at a wooden dock, providing easy access to the water. Two lounge chairs sit on the grass, inviting relaxation by the river.

Home in Lake Luzerne

4.95 out of 5 average rating, 94 reviews

Peaceful Adirondack Waterfront

Perfect Riverfront home offers a truly five star accommodations. Your Adirondack get away begins with a private 50 foot waterfront with walk down steps for easy access into the river. Enjoy using the supplied kayaks on seven miles of clear sparkling Hudson River, flowing fresh water in daily directly from the Sacandaga River. Our private dock is ready for your boats and jet skis to be anchored.