Holiday rentals with a kayak in Berkshire County

Find and book unique kayak rentals on Airbnb

Top-rated rentals with kayak in Berkshire County

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

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Guest favourite

Home in Becket

4.93 out of 5 average rating, 119 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 favourite

Home in Great Barrington

4.96 out of 5 average rating, 142 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 favourite

Flat in Lanesborough

5.0 out of 5 average rating, 23 reviews

Cozy Berkshire Waterfront Home

Welcome to our charming waterfront home on Pontoosuc Lake! The Berkshire Lakescape is perfect for a romantic getaway for a couple or two, or a solo adventure away. Soak in lake views from the deck or try to catch a stunning sunset from the water’s edge. Kayak straight from our backyard and return for marshmallows at the firepit. Explore Berkshires' culture and outdoor activities - Tanglewood, Mount Greylock, and more are just a short drive away. We can't wait to host you for a memorable stay.

Guest favourite

Cottage in Hinsdale

4.99 out of 5 average rating, 141 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 favourite

Home in Sandisfield

5.0 out of 5 average rating, 20 reviews

Waterfront oasis in heart of Berkshires

This house is a one-of-a-kind waterfront retreat that offers total privacy, spa-like serenity, and easy access to all the Berkshires has to offer. You'll find a fully stocked, professional-grade kitchen, a dining room perfect for family meals, and a living room with a wood-burning stove. There are two bedrooms downstairs and two upstairs. The house is close to skiing and tubing at Butternut, farm-to-table dining, shopping in Great Barrington and Lenox, Jacob's Pillow, and Tanglewood.

Superhost

Cottage in Canaan

4.9 out of 5 average rating, 126 reviews

Plan your Berkshires by the lake

Very comfortable three-bedroom cottage in a quiet, private association on Queechy Lake. There is also a pullout queen size couch. 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 is also 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!

Guest favourite

Flat in Canaan

4.97 out of 5 average rating, 89 reviews

Queechy Lake Carriage House

Comfortable, two bedroom 2nd floor apartment, fully equipped kitchen, well-lit open living space, a short walk to our association’s beach, fishing docks, kayak launch, 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.

Superhost

Cabin in Lanesborough

4.8 out of 5 average rating, 54 reviews

Cozy stream-side cabin

Nestled in the heart of the Berkshires along a cool, fresh-water stream. This 1-bedroom 650 sq. ft. bungalow has been completely renovated and ready to welcome you. It is conveniently located to many area attractions and is situated near the base of Mount Greylock, the highest peak in Massachusetts. The main living space has a working brick fireplace, cathedral ceilings, recessed lighting, a French door, real pine wood walls, and a loft that overlooks the main living space.

Guest favourite

Cabin in Monterey

4.95 out of 5 average rating, 252 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 favourite

Home in Becket

5.0 out of 5 average rating, 21 reviews

Secluded lakeside charmer

Kick back and relax in this comfortable and cozy antique filled cottage. Direct lake access for kayaking, with beach 3 minute walk away. Enjoy the screened porch or open deck. Light a fire on a cool night. Conveniently close to Jacobs Pillow, Tanglewood, theaters, and all the beautiful Berkshire towns: Lee, Lenox, Stockbridge, Great Barrington. Excellent hiking trails close by. Variety of casual or fine dining restaurants close by. Not suitable for children under 10

Guest favourite

Cottage in Becket

4.96 out of 5 average rating, 134 reviews

Cozy lakeside cottage

Two-bedroom cottage on the lake with a dock nestled in the woodsy Sherwood Forest Community. Relax with the whole family at our quiet and peaceful oasis. You can swim, fish, kayak, and canoe in the water right from our private beach. Great place for a lakeside campfire at night. Our dock is perfectly situated for practicing yoga, meditation or quiet contemplation. Please note that accessing the house as well as getting down to the dock requires climbing stairs.

Guest favourite

Home in Egremont

4.93 out of 5 average rating, 56 reviews

Modern and Stylish Country Lakeside Cottage

Direct view of and use of waterfront. One king bedroom, one bath, cook's kitchen with high end appliances. Banquette seating surrounded by banks of windows. Large living room with gas fireplace. Small loft area above living room with queen bed. Cathedral ceilings. Large bath en suite. Washer/Dryer. Patio and fire pit for marshmallows. Boat/swim in summer or ice fish/skate in winter. A perfect spot to enjoy the outdoors. Stone’s throw from Catamount and Butternut.