Holiday rentals with a kayak in Pioneer Valley

Find and book unique kayak rentals on Airbnb

Top-rated rentals with kayak in Pioneer Valley

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

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Guest favourite

Cottage in Becket

4.94 out of 5 average rating, 215 reviews

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 • Canoe & 2 kayaks • 50" smart TV and 4 Google Smart Speakers • 1 Gigabit Wi-Fi 'gorgeous with amazing views' • 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

Guest favourite

Chalet in Stamford

4.92 out of 5 average rating, 100 reviews

Peaceful VT Chalet w/ Mountain View’s

My peaceful 3-bedroom chalet has everything you need for your VT trip. The house comes with a washer, dryer, Roku TV’s, pullout queen couch. 2.5 bathrooms, indoor elec. fireplace, outdoor fire pit and fully equipped kitchen.Short driving distance to several popular golf courses, shops, restaurants, breweries, fishing, white water rafting, hiking, kayaking, ATV/snowmobile trails, & mountain slopes. An ideal base to explore the Green Moutain National Forests (VT) or the Berkshire Mountains (MA).

Top guest favourite

Flat in Coventry

5 out of 5 average rating, 109 reviews

Hide Away at Rock Farm UConn Private BnB “5 Star”

Enjoy a peaceful stay at The “Hide Away” on Rock Farm. The 1000+ sf of space is surrounded by woods 600ft off the road. Well lit, all amenities of home. Enjoy the private deck on sunny mornings. 5 min walk to Bolton Lakes. Fishing, Kayaking & trails. Central to many locations & venues. See our VIP GUEST BOOK for The Get Away on Rock Farm & The Hide Away at Rock Farm. A no-shoe, clean place, comfortable homey feel. 5⭐️ Needing less space? Visit the Get Away https://www.airbnb.com/h/onrockfarm

Top guest favourite

Cottage in Southwick

4.98 out of 5 average rating, 112 reviews

Lake View, Hot Tub, 4 Kayaks, Central AC, Fire Pit

Congamond House is the perfect lake home getaway. Kayak the calm North Pond. Get your breathtaking pics of the surrounding wildlife. Cuddle up on the deck and enjoy the stars or relax in the hot tub under the deck while gazing upon the lake. This 1500 sq ft cottage is the perfect size for 2 families. (4 adults w/4 kids or 6 adults) Minutes from Six Flags Amusement Park, the Big E and the Basketball Hall of Fame 4 Kayaks that seat 6. Paddles and life vests provided 20 min. from Bradley Airport

Top guest favourite

Home in Vernon

4.99 out of 5 average rating, 153 reviews

Luxe Bolton Lake

Enjoy beautiful Middle Bolton Lake and relax in the stylish comfort of our 3 bedroom/3 bathroom architecturally-designed home. The Luxe lake house features an expansive waterfront, outdoor jacuzzi, gorgeous primary bedroom suite w/ private shower and tub, artistic furniture, cozy fireplace, coffee bar, complimentary snacks, fast WiFi, large deck, fire pit, kayaks, vintage aluminum canoe, board games, and much more. Come stay at the Luxe lake house and make memories that will last a lifetime!

Top guest favourite

Cottage in Hinsdale

4.99 out of 5 average rating, 155 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 Becket

4.94 out of 5 average rating, 150 reviews

Lake front retreat - Stylish Berkshire home

Absolute privacy! Escape to this beautifully renovated mid-century home w/ 4 bedrooms on Long Bow Lake. Featuring stylish wood floors & modern design, the cozy dining room boasts a gas fireplace. This family-friendly retreat offers exclusive lake frontage complete w/ a dock & 4 kayaks for endless fun! Enjoy serene moments on the screened porch, fire up the Weber grill, or challenge each other to ping pong. Located just 20 mins from Downtown Lee, outlets, hikes, & Otis Ridge skiing

Top guest favourite

Cabin in Whitingham

4.99 out of 5 average rating, 107 reviews

Cozy Cabin ~16 Mi. to Slopes on 10 Acres of Woods!

Tucked away in the bends of Burrington Hill Road, you’ll find our family’s Whitingham Wonderland, where our Irish touch is sure to make you feel at home and our NYC energy will keep you entertained. Our home is stocked with games for all ages as well as multiple Smart TVs, a fire pit and grill. To enjoy all Vermont has to offer we are only 30 minutes from Mt Snow and 45 from Stratton with the towns of Wilmington & Dover peppered along the way. Come make memories to last a lifetime!

Guest favourite

Home in Coventry

4.98 out of 5 average rating, 114 reviews

Cozy cottage 5 minutes from UConn

Wake up to the morning sun over the lake in the loft, or rise after the sun in one of the two back bedrooms. Enjoy a warm morning coffee while enjoying the lake view from the bar top overlooking the water and watch for the Swans, Bald Eagles, and Blue Herons. After a hike on the trails, kayaking up the lake into conservation land, or fishing off the dock, relax in the hot tub. As the sun sets over the trees cuddle up on the couch with a good book and keep an ear out for the owls.

Guest favourite

Cottage in Orange

4.91 out of 5 average rating, 185 reviews

The Lake Cottage: A Sweetwater Stay

Welcome to Mattawa Cove! Originally built as an Ice Fisherman's shack, this tiny house is unapologetically elegant and understated. The private dock can be viewed from the wall of windows in the open living space. Walk to the shore, sit with your feet in the water, swim, fish, or kayak. It’s the ultimate, all-year romantic getaway. With excellent Wi-Fi, you can stay as connected as you'd like to the outside world. 1.5 hours from Boston or Providence. 3.5 hours to NYC.

Guest favourite

Cottage in Lanesborough

4.84 out of 5 average rating, 280 reviews

Wildlife Lakeside Cottage; views/wildlife

Fully furnished and remodeled with new upgrades in Spring 2025 including a cathedral master bedroom suite with a full bath. Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. Incredible amount of wildlife, especially all types of birds. The home has sunny views everywhere. Seasonal weeds do grow in the adjacent lake which can impact water activities, especially in the summer months. Sleeps 6. Ther are two full and one 1/2 baths.

Guest favourite

Cabin in Petersburgh

4.93 out of 5 average rating, 242 reviews

Cozy Retreat in the Trees

Time travel to 1958 in this architectural gem! This mid-century modern glass and wood cabin is 300 yards away from a charming small lake. The house is NOT on the lake itself, but it is surrounded by trees in a lovely secluded spot. The only heat is a wood stove... but there is a 4-person cedar barrel sauna in the woods that is electric. A classic 1952 Spartanette travel trailer serves as an extra bedroom. This is a true retreat for romance and adventure.