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Vacation rentals with a kayak in Berkshire County

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Top-rated kayak rentals in Berkshire County

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

Guest favorite
Home in Becket
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.
$256 per night
Guest favorite
Home in Great Barrington
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.
$371 per night
Guest favorite
Cottage in Hinsdale
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.
$175 per night

Popular amenities for Berkshire County kayak rentals

House rentals with a kayak

Guest favorite
Home in Sheffield
A Private Peninsula Retreat In The Berkshires!
$316 per night
Guest favorite
Home in Becket
Lakefront in the Berkshires
$224 per night
Guest favorite
Home in Becket
Little Longbow Lakefront Chalet
$148 per night
Guest favorite
Home in Becket
Lindal Cedar Berkshires Lake House
$388 per night
Guest favorite
Home in West Stockbridge
Heart of the Berkshires - Bright, Cozy, Near Lake
$426 per night
Superhost
Home in Becket
New Shaw Pond Skytop Retreat in the Berkshires
$275 per night
Guest favorite
Home in Becket
Secluded lakeside charmer
$225 per night
Guest favorite
Home in Canaan
Secluded Mountain Top Lake View in Canaan, NY
$344 per night
Guest favorite
Home in Pittsfield
Ski The Berkshires at Family friendly Hygge House
$328 per night
Guest favorite
Home in Lee
Berkshire's Manor for Lasting Memories
$285 per night
Superhost
Home in Monterey
Peaceful 3bd Near the Lake with Kayaks!
$200 per night
Guest favorite
Home in Canaan
Beautiful Lake Front Cabin
$300 per night

Cottage rentals with a kayak

Guest favorite
Cottage in Hinsdale
Berkshires - Charming Lakefront Cottage
$250 per night
Superhost
Cottage in Hinsdale
Berkshires Lakeview Getaway Cottage
$229 per night
Guest favorite
Cottage in Pittsfield
Charming lakeview cottage w/ kayaks, Richmond Pond
$180 per night
Cottage in Becket
A Magical Spot on Little Robin Lake
$235 per night
Guest favorite
Cottage in Otis
Berkshire lakefront cabin with modern luxuries
$499 per night
Cottage in Becket
Cozy Cottage on the Lake
$179 per night
Guest favorite
Cottage in Lanesborough
Norte Maison 2 beds 2 Baths Minutes to Jiminy Peak
$302 per night
Guest favorite
Cottage in Stockbridge
Stockbridge Summer/Fall - 3BR/2BA Cottage by Lake
$411 per night
Cottage in Hinsdale
Modern one bed room cottage loft on beautiful Lake
$225 per night
Guest favorite
Cottage in Monterey
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
$163 per night
Cottage in Monterey
mountain refuge
$126 per night
Guest favorite
Cottage in Canaan
Private Berkshire Cottage with Queechy Lake Views
$190 per night

Cabin rentals with a kayak

Superhost
Cabin in Lanesborough
Cozy stream-side cabin
$176 per night
Guest favorite
Cabin in Hinsdale
Relaxing Berkshire cabin on Lake Ashmere
$229 per night
Guest favorite
Cabin in Becket
Cozy Rustic Lakefront Cabin
$275 per night
Guest favorite
Cabin in Otis
Enjoy 43 Acres on Two Ponds!
$464 per night
Guest favorite
Cabin in Tolland
Lake View Cabin in the Berkshires
$220 per night
Guest favorite
Cabin in Stockbridge
Cozy Stockbridge Cabin - Walk to Beach & Lake!
$321 per night
Guest favorite
Cabin in Pittsfield
Summer Cottage in the Berkshires
$175 per night
Cabin in Stockbridge
Lakeshore cabin with private beach and dock
$232 per night
Cabin in Tolland
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
$188 per night

Destinations to explore