
Vacation rentals with a kayak in Great Barrington
Find and book unique kayak rentals on Airbnb
Top-rated kayak rentals in Great Barrington
Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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.

Hilltop Retreat w Magic View! 15 mins to Butternut
Please enjoy our little slice of paradise! Perched just up the hill from Lake Garfield, The Hupi House offers a truly magical view of the lake and mountains for miles beyond. Let breathtaking sunsets be your evening entertainment! Inside you will find a stocked kitchen, high-quality appliances and bedding, fast wifi, and wooded seclusion. Outside you will find swimming, kayaking, hiking, leaf-peeping, star-gazing, skiing...Minutes to Ski Butternut, Great Barrington, Jacob's Pillow, Tanglewood.

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.

Modern Mid-Century Cottage - Hike, Swim & Shop!
Let all your worries fade away in this beautifully remodeled modern cottage! Our 3 bedroom, 2 bath can sleep 8 adults in 2 Queen Beds, 2 Twin Beds and a Queen Sleeper Sofa. Relax by the fire pit out back or take out our 2 two person Kayaks and enjoy the lake in the summer, visit Catamount Ski Resort or other nearby ski mountains in the winter. The large, custom dinner table seats 8 comfortably with lots of room to hang, play games, watch movies and more. Guests must be 25 years old to rent.

HEAVEN ON EARTH - Hudson Riverfront Home
Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access year round. We provide kayaks & stand up paddle board. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Fish right off the lawn. Enjoy brunch, dinner or high tea in the Gazebo suspended over the Hudson with a private chef (inquire about availability). Explore Hudson, Saugerties, Woodstock....honestly, you'll not want to leave.

Lakefront | Pvt Dock | Kayaks | Firepit | 1G | W/D
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 (access via uneven steps) • Canoe & 2 kayaks • Smart TV & 4 Google smart speakers • 1 Gigabit Wi-Fi • 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

Lovely Berkshire Home
"We are located in the heart of America's cultural epicenter known as the Berkshires. Known as the "Gatehouse" to upscale Erskine Park, this truly one of a kind Craftsmen inspired home is filled with unique features and materials seldom found including eucalyptus and Brazilian Cherry flooring, Jerusalem stone and porcelain plank tiles. Inviting color and intriguing design elements make this an extraordinarily pleasing home. Every detail has been thoughtfully considered within. Dreamy!"

Rustic Pond Cabin: Nature, Stars & Serenity
Serene rustic cabin in Colebrook, Ct in beautiful Litchfield County! Cozy King bed under skylight, queen downstairs, woodstove and all the comforts of home. Pure clean pond- swim, fish, canoe n kayak! Sits far from main roads on quiet back road. Can walk, run or bike to local trails or stay and walk the trail around the pond, have campfires outside in firepit! Cleaned by me, no crazy rules n and surrounded by nature! Private Great WIFI! Close to quaint ski resorts n dispensaries

Waterfront, Dog & Family Friendly, Cozy Cottage
El Girasol, "The Sunflower," a sunny, family and pet friendly cottage on the Esopus Creek in the Catskill Mountains. Our home is fully furnished with global & vintage finds. This charming cottage has 2 beds, spacious living room with a big, comfy sleeper sofa and cozy electric fireplace & fully equipped kitchen combined with a dining room. Creek access, BBQ, fire pit, fenced in backyard, & 2 decks makes our home a great destination for a relaxing getaway with family, friends and pets.

Lakefront escape w/ Breathtaking Bald Eagle Views
Wake up to bald eagles soaring past floor-to-ceiling windows in the lakefront great room. Relax by the fireplace or unwind in the cozy TV room. A spacious kitchen makes cooking easy. Upstairs: 4 bedrooms (2 king, 2 queen, all w/ desks) + 4 full baths (3 w/ showers, 1 w/ tub). Enjoy fast Wi-Fi, seasonal lake access, dock, and deck. Swim or kayak at your own risk (no guest boats at dock per insurance). Your lakeside getaway awaits! Airbnb has a strict NO Events policy which we follow.

Copake Lake Cottage Near Hiking and Waterfalls
Renovated, art-filled cottage just 500 ft from Copake Lake. This 2 bedroom 1 bathroom house is also close to hiking trails, waterfalls, apple picking, & a winery in the fall, and in winter, there’s skiing at Catamount, and a distillery nearby. A house for all seasons! Please note the house is 5 houses back and across a quiet road from the lake, and the dock is in the lake from the beginning of May to mid-September. But there is plenty to do up here during the rest of the year!

Creekside Cottage
Set on the beautiful Esopus Creek, this lovely 2 BR, 2 bath home is perfect for a get-away w/family, friends or a romantic or creative retreat. It's just a 15-20 minute drive to the quaint Village of Saugerties, Kingston, Woodstock & Rhinebeck. Sit & watch the river run by on the screened porch or on the deck down by the river's edge, bbq (4 burner gas stove), play board games, take a kayak or swim in the river. Kitchen w/full amenities. Pets are not allowed unless pre-approved.
Popular amenities for Great Barrington kayak rentals
House rentals with a kayak

Lake House in Averill Park, NY (age 30+ excl kids)

Everything on one floor 2 Bdrm/1.5 Bth & Pets Ok

Escape to Lakefront Leisure—Amazing views!

Magical Waterfront Escape on the Esopus Creek

Twin Island Lake House • Hot Tub

Majestic lake front house

Waters' Edge on the Esopus

Lakefront Fall Escape: Kayak, Fish, Firepit!
Cottage rentals with a kayak

Chic Cottage at Richmond Pond

Plan your Berkshires by the lake

Kayak, pet a Highland cow, have dinner in Hudson!

Hook, Wine and Sinker!

Waterlily Lakehouse - Modern+Waterfront+Retreat

Private Hudson Valley Lakefront-Kayak, SUP, Fish,

Lake Front Cottage with Sun Soaked Terraces

Pet friendly Cottage on Lake; Hike, Swim, Kayak
Cabin rentals with a kayak

"Family Cabin: Hot Tub, Pond, Games, Sunset, Pet!"

Catskills Cabin on 100 Wooded Acres, Private Lake

Glamping in the Berkshires w/ car charging station

Wildlife Retreat in the Forest

Secluded luxury: modern riverfront fishing cabin

Charming Lakefront Cabin with Hot Tub

The June Farms Lake House

Enjoy 43 Acres on Two Ponds!
Quick stats about vacation rentals with a kayak in Great Barrington

Total vacation rentals
Explore 20 vacation rentals in Great Barrington

Nightly prices starting at
Great Barrington vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 810 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Great Barrington vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Great Barrington rentals

4.8 Average rating
Great Barrington stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Mount Pocono Vacation rentals
- The Hamptons Vacation rentals
- Rentals with a fire pit Great Barrington
- Fitness-friendly rentals Great Barrington
- Rentals with outdoor seating Great Barrington
- Rentals with a hot tub Great Barrington
- Cabin rentals Great Barrington
- Rentals with a patio Great Barrington
- Rentals with pools Great Barrington
- House rentals Great Barrington
- Apartment rentals Great Barrington
- Rentals with a fireplace Great Barrington
- Rentals with lake access Great Barrington
- Family-friendly rentals Great Barrington
- Waterfront rentals Great Barrington
- Rentals with a washer and dryer Great Barrington
- Pet-friendly rentals Great Barrington
- Rentals with a kayak Berkshire County
- Rentals with a kayak Massachusetts
- Rentals with a kayak United States
- Hunter Mountain
- Six Flags New England
- Jiminy Peak Mountain Resort
- Thunder Ridge Ski Area
- Berkshire East Mountain Resort
- Windham Mountain
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Kent Falls State Park
- Zoom Flume
- Walkway Over the Hudson State Historic Park
- Catamount Mountain Ski Resort
- Bushnell Park
- Norman Rockwell Museum
- Taconic State Park
- Wintonbury Hills Golf Course
- Mount Southington Ski Area
- Mount Sugarloaf State Reservation
- Hartford Golf Club
- Bright Nights at Forest Park
- Mount Tom State Reservation
- Hunter Mountain Resort
- Bousquet Mountain Ski Area




