Vacation rentals with a kayak in Hampshire County

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Hampshire County

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

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Guest favorite

Home in Williamsburg

4.91 out of 5 average rating, 23 reviews

Cute and Cozy Lake Cottage

Small cottage with lake view & access. No motorboats, pristine and quiet lake (SUPs & kayaks provided). Rare, but true, aurora borealis sitings on this lake (see pic)!. Cottage abuts the DAR State Forest, which has 15 miles of hiking (for all levels), birdwatching, and XC skiing. 25 min drive to Northampton, known as an academic, artistic, musical, and countercultural hub and home to Smith College. 30 min drive to Berkshire East Ski Resort and Stumps XC Skiing Center, others about 50 mins away.

Guest favorite

Home in Becket

4.96 out of 5 average rating, 26 reviews

Rustic 3-bedroom Hidden Gem Amongst the Forest

Nestled deep in the Sherwood Forest neighborhood, with access to 4 separate lakes, this hidden gem features unique architectural character and has plenty of room for the entire family! The first floor has an open concept, with fully loaded kitchen, gas range, dishwasher, and farmhouse sink. The gorgeous stone fireplace runs throughout and provides a stunning centerpiece to the home and a warm space to gather. Upstairs you’ll find three spacious bedrooms, including a master with fireplace.

Guest favorite

Apartment in South Hadley

4.92 out of 5 average rating, 39 reviews

River front property

Unique 2 bedroom guest house on the Connecticut River in South Hadley, Sleeps 8 1 bathroom Covered parking Dock available Kayaking Boat rental available Paddle bikes and boards Views Fire pit Tour boat next door at Brunelle’s Marina. Patio Ice machine Boathouse restaurant Village commons 1 mile away McCrays farm 1 mile away Ledges golf course 2 miles away Malls etc. 15 min MGM casino 15 min Basketball hall of fame 15 min Airport 45 min Amtrak 10 min Mt sugarloaf 20min. Hiking trails

Guest favorite

Home in Plainfield

4.73 out of 5 average rating, 150 reviews

Sleeps upto 10ppl, Wi-Fi w/ fireplace

Secluded Berkshire house surrounded by 10,000 acres forest is with marked trails & pond that sleeps up to 10 people comfortably. Central air & heat, fireplace, propane BBQ & charcoal BBQ & smoker BBQ, Fibre high-speed WiFi gigabit internet (new in January 2020), Roku streaming device with Netflix & Amazon Prime & hundreds more channels, gazebo, private pond, comfy mattresses/beds, 2 bathrooms, new laundry dryer, 16 foot C shaped couches, indoor garage parking, vegetable gardens, kayaks & more.

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.

Cabin in Westhampton

5.0 out of 5 average rating, 3 reviews

Lakefront Westhampton Cabin w/ Beach + Kayaks!

Plenty of opportunities for outdoor adventure await when you stay at this incredible Westhampton vacation rental! Featuring on-site access to Pine Island Lake, a private beach, kayaks, and more, this beautiful 3-bedroom, 1.5-bath cabin is perfect for any family looking to spend some time surrounded by nature. Relax in the cabin’s water-facing screened porch, explore nearby hiking trails, or make the short drive to Downtown Northampton to check out local restaurants and shops during your stay!

Guest favorite

Home in Becket

4.88 out of 5 average rating, 17 reviews

Lakefront Cottage on Private Beach

House is right on the lake! Step into the water or the dock from the private flat yard! Enjoy the amazing lake view from the patio or the glass sunroom! Located in the heart of the Berkshires - 10 mins from Jacob's Ladder, 20 mins from Lee Outlets, and 30 mins from the Norman Rockwell Museum or Tanglewood. Enjoy farm-to-table restaurants in the area, or make home-cooked meals using the well-equipped kitchen. House is surrounded with trees and perfect for a quiet and relaxing getaway!

Guest favorite

Home in Otis

5.0 out of 5 average rating, 26 reviews

Big Pond Hideaway

Truly off the beaten path at the end of a winding dirt road, Big Pond Hideaway is a quiet and secluded lakefront retreat tucked away in the woods, less than 100 steps from beautiful Big Pond, a 300 acre fish filled lake. Recently renovated with lots of windows and views of the lake, it is stylish, bright and open with an updated kitchen & appliances, gas stove, grill, wood stove, outdoor shower and plenty of outdoor seating on the decks or around the patio fire-pit.

Guest favorite

Cottage in Becket

4.95 out of 5 average rating, 132 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 favorite

Home in Amherst

4.88 out of 5 average rating, 59 reviews

Classic New England Country House, 5 min to town

Lovely 1850's farmhouse with lots of natural light, woodstove, and great book collection nestled on 2 acres along a pretty rural road. Comfortable, peaceful, & convenient. Perfect for a writing/artistic retreat, romantic getaway, or family gathering. Fantastic 2 acre yard with giant maple trees & gardens. There are two desks and a large dining table plus great wifi (xfinity) for remote work. Host is a 5-college professor with local knowledge and suggestions.

Superhost

Vacation home in Becket

4.95 out of 5 average rating, 42 reviews

Perfect Serene Waterfront All Season Retreat!

Enjoy everything the Berkshires has to offer from this beautiful, secluded, nicely renovated waterfront house set on two wooded acres of forested land. Explore the stream that runs through the property, or just sit on the large deck or down by the crystal clear lake and listen to the sounds of nature while feeling the warm sun on your face. Very private--just one near neighbor. The sunny house has 2 bedrooms, study with sofa bed, 2 full baths, full kitchen!

Farm stay in Ashfield

4.99 out of 5 average rating, 78 reviews

Blue House Farm and Gardens

Blue House Farm & Garden is back after a 3-year COVID hiatus. Your lovely peaceful Studio shares a wall with our 1794 farmhouse but has its own entrance, porch and privacy. Enjoy the tranquility of our land but still be only 2.4 miles from the center of Ashfield, 30 minutes from Northampton and Old Deerfield, less than 20 minutes to Berkshire East Mountain Resort, 30 minutes to Notchview for cross country skiing and snowshoeing, and 45 minutes to Mass. MOCA.