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

Home in Becket

4.93 out of 5 average rating, 118 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.

Nov 23 – 30

€ 385 per night

Guest favorite

Home in Great Barrington

4.96 out of 5 average rating, 140 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.

Nov 17 – 24

€ 447 per night

Guest favorite

Apartment in Lanesborough

5.0 out of 5 average rating, 22 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.

May 15 – 22

€ 169 per night

Guest favorite

Home in Becket

5.0 out of 5 average rating, 13 reviews

Lindal Cedar Berkshires Lake House

Welcome to Excalibur Lake Lodge in the Berkshires. This beautiful lakefront contemporary Lindal Cedar custom home, with architecture that intentionally focuses on the peaceful lake view, has been designed for your comfort and relaxation. Explore the Berkshires year round and see what the area has to offer: from skiing in the winter, to Tanglewood and Jacob’s Pillow in the summer and leaf peeping in the fall. Or just enjoy the tranquility of our lakefront lodge for a rejuvenating weekend away.

Apr 19 – 26

€ 469 per night

Guest favorite

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.

Apr 1 – 8

€ 263 per night

Guest favorite

Home in Great Barrington

5.0 out of 5 average rating, 34 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. *sauna and hot tub coming soon!

Dec 14 – 21

€ 342 per night

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!

Sep 24 – Oct 1

€ 257 per night

Guest favorite

Apartment in Canaan

4.96 out of 5 average rating, 83 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.

Sep 5 – 12

€ 97 per night

Guest favorite

Cabin in Monterey

4.95 out of 5 average rating, 251 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.

Aug 6 – 13

€ 414 per night

Guest favorite

Home in Becket

5.0 out of 5 average rating, 20 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

Sep 15 – 22

€ 282 per night

Guest favorite

Cottage in Becket

4.95 out of 5 average rating, 131 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.

Nov 20 – 27

€ 285 per night

Guest favorite

Home in Becket

4.91 out of 5 average rating, 56 reviews

Little Longbow Lakefront Chalet

Welcome to your Berkshire Oasis! This rustic lakefront chalet is ideally located right in the heart of the Berkshires in a private community, Sherwood Greens. Only minutes away from Jacobs Pillow, The Appalachian Trail, Otis Ridge Ski Resort, Butternut Ski Resort, and Tanglewood, there are plenty of activities all year round! You are a short drive to Lee, Lenox, Stockbridge, Pittsfield, and Great Barrington.

Mar 10 – 17

€ 400 per night