Vacation rentals with a kayak in Western Massachusetts

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Western Massachusetts

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

0 of 0 items showing

1 of 3 pages

Guest favorite

A cozy red cottage sits amidst tall trees, featuring a spacious deck with lattice work. Natural light filters through the windows, and a serene lake can be seen in the background, surrounded by lush greenery.

Cabin in Bradford

5 out of 5 average rating, 5 reviews

Little Red Wing 50s Lake Cabin

Cozy 1950's waterfront cottage on Lake Massasecum! In the Winter - Skiing is close by. Snowmobiling, Ice Fishing, and Cross County Skiing are allowed on the lake. It’s very important to test the ice for safety. In the Summer - Power boats are allowed on Lake Massasecum and it is also the perfect place for canoes, kayaks, great fishing and bird watching! Three kayaks, one canoe, and one paddle board are available for use with cabin rental. Also comes with the use of a private swim platform.

Guest favorite

An aerial view showcases a single-story house nestled in a spacious yard by Johnson’s Pond. The backyard features a wooden deck with stairs leading down to private water access, along with nearby docks for recreational use.

Home in Coventry

4.86 out of 5 average rating, 131 reviews

Awesome 3 bed vacation lake house. Great location!

Three bedroom house right on Johnson’s Pond with private water access right in the back yard. House features queen master with deck overlooking the pond. 2nd bedroom features a full bed with twin bunk bed above along with a stand alone twin bed. 3rd bedroom has a queen bed. Perfect for one or two couples to share. Full kitchen and laundry along with WiFi and streaming services. Use of 2 kayaks and pedal boat. Just two miles from I-95, so everything in southern New England is just minutes away!!

Guest favorite

A spacious deck overlooks a serene lake, featuring a patterned outdoor rug and a table with seating. An umbrella provides shade, while a grill stands ready for use. Vibrant flowers add color, complementing the clear blue sky and peaceful surroundings.

Home in Exeter

4.97 out of 5 average rating, 118 reviews

Come relax at Lakeside Landing

Come relax and enjoy lakefront living in this 2 bedroom, 1 bath house on Boone Lake. 1st BR offers a king size bed and 2nd BR offers a twin over full bunk bed with a trundle. Enjoy open concept living with beautiful views of the lake. Inside you will find wifi, streaming on 3 tvs, Wii, board games, puzzles and books. Relax on the large deck, enjoy yard games or use the 2 kayaks, canoe or paddle board. A perfect place for a relaxing family getaway. Ring camera at front door only for security.

Top guest favorite

A modern cabin in a secluded setting is depicted, featuring a red exterior and a sloped roof. The cabin is positioned near a serene body of water, surrounded by vibrant autumn foliage reflecting in the water. A clear blue sky adds to the tranquil atmosphere.

Cabin in Stoddard

4.97 out of 5 average rating, 157 reviews

Secluded Renovated Retreat Surrounded by Nature

Get away from it all in a secluded, yet modern cabin, which guests have loved for its "silence and beauty" and called "peaceful" and "serene". Located on the Lakefalls Estate, which maintains the roads, Mended Oar features heated floors throughout, a well-furnished kitchen with quality appliances and equipment, and luxurious linens. Hike the many trails outside the door on the snowshoes you'll find, then come inside to enjoy the wood burning fireplace (wood provided) and play a board game.

Top guest favorite

Cottage in Southwick

4.98 out of 5 average rating, 104 reviews

4 Kayaks Fire Pit & Lake Views from Hot Tub

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

Superhost

A charming lake house is positioned by the water, featuring a quaint peaked roof and large front windows that bring in natural light. A porch offers seating, while a grill is visible to the left. Surrounding greenery enhances the tranquil setting.

Home in Westminster

4.82 out of 5 average rating, 149 reviews

Lakefront, view of ski mtn, firepit, kayaks, dock

A charming lake house with a magnificent view of a ski mountain — Wachusett Ski Resort (voted #1 in MA). Newly-renovated, 650 square foot cabin with a wall unit AC, fire pit, grill, smart TVs, kayaks, paddle board, and all the amenities you’ll need. (FYI: We also own another lakefront Airbnb right down the street that accommodates 10 guests. Ask for link.) *A brand new retaining wall and dock will be installed May 2024. This will extend and even out the lawn for nights around the firepit!

Guest favorite

A welcoming exterior of a cabin is shown, featuring a light gray façade with a sloped roof and large arched window. A railing borders the porch that provides river views. Lush green grass and autumn foliage frame the scene, enhancing the tranquil riverside setting.

Cottage in Clifton Park

4.83 out of 5 average rating, 92 reviews

Waterfront cabin 9 - Kayaks - 24 mins to Toga

Watch the boats pass by as you enjoy the views from this stylish riverfront camp in the heart of the Capital District. Towpath Landing is a collection of 18 waterfront cabins that I am bringing back to life. Cabin Bleu has expansive views of the Erie Canal/Mohawk River, fully stocked kitchen with granite, huge front porch with table, grill and relaxing chairs PLUS a screened in back porch for relaxing with a woods view. This is served by filtered river water so bring drinking water.

Top guest favorite

A waterfront property is positioned on a hillside, with a tiered landscape leading to a private dock. The building features multiple decks and large windows, offering unobstructed views of the surrounding nature. Green lawn and rocky pathways create a welcoming outdoor space.

Home in Queensbury

4.99 out of 5 average rating, 169 reviews

Sunset Bay: Amazing waterfront w/ dock on 5 acres!

SUMMER 2025 FULL/FALL OPEN Amazing waterfront property on 5 acres with west-facing sunsets overlooking the water & mountains. Private. Two-tiered deck, stone patio, & hot tub, open floor plan living/dining/kitchen. Private dock to swim off of and/or dock your own boat (May-Sept). Includes attached apartment with bedroom, kitchen, bathroom, and living room. Most bedrooms can flex to be King beds or split to make twins. Be close to everything yet away from it all.

Guest favorite

Home in Otis

4.96 out of 5 average rating, 108 reviews

Direct Lakefront Home on Otis Reservoir Giant Yard

Year round retreat directly on Otis Reservoir offering 62’ of lake frontage on MA largest and fully recreational lake. Enjoy the lake views right from our docks, Solo Stove firepit, expansive deck, main floor or bedrooms. The house sits 100 yards back from the lake leaving a large lawn for outdoor activities. Updated and renovated in 2021! Many local snowmobile trails and ski resorts too! Heated garage and 2nd driveway for larger trucks/trailer or RV's.

Guest favorite

A private campsite is surrounded by lush greenery with a view of the water. A safari-style tent and deck are positioned among trees, complemented by a seating area and a hammock. Sunlight filters through leaves, enhancing the natural setting.

Campsite in Lake Katrine

4.96 out of 5 average rating, 169 reviews

Private Waterfront Winter Camping Experience

**WATER IS NOW ON FOR THE 2025 SEASON! Owner operated private single campsite! This quaint little tent and private deck are nestled among the trees on the banks of the Esopus Creek in a great little neighborhood! A way to get back to nature without truly leaving it all behind. A one of a kind private waterfront escape with a fire pit & electric! WATER ACCESS AND KAYAKS NOW AVAILABLE! Enjoy a 2.5 mile stretch of the Esopus creek!

Top guest favorite

A private waterfront area is shown with clear, calm river water lapping against a pebbled shore. A pontoon boat is moored at a wooden dock, providing easy access to the water. Two lounge chairs sit on the grass, inviting relaxation by the river.

Home in Lake Luzerne

4.95 out of 5 average rating, 94 reviews

Peaceful Adirondack Waterfront

Perfect Riverfront home offers a truly five star accommodations. Your Adirondack get away begins with a private 50 foot waterfront with walk down steps for easy access into the river. Enjoy using the supplied kayaks on seven miles of clear sparkling Hudson River, flowing fresh water in daily directly from the Sacandaga River. Our private dock is ready for your boats and jet skis to be anchored.

Superhost

A tranquil lakeside area features a private dock with lounge chairs and an umbrella, providing a place to relax by the water. Nearby, a wooden deck leads to the charming cottage, surrounded by lush greenery and trees, creating a serene atmosphere.

Cottage in Red Hook

4.9 out of 5 average rating, 205 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

Get away from it all to your little slice of paradise. Kayak, swim and rest. Just a hop skip and jump from the city. A blue stone pathways leads to your own private charming cottage overlooking a beautiful spring fed lake with your own private Hot Tub OPEN ALL YEAR ROUND and lake front oasis. Completely surrounded by perennials, and native trees. Lake dock, Hammock and kayaks await you.

0 of 0 items showing

What guests are saying

Spacious Classic Lakefront Home with jet tub

4.98 out of 5 average rating, 55 reviews3 months ago

I came here in the dead of winter for a writer's retreat with a fellow writer- AND I WOULD DO IT AGAIN! It was a beautiful and inspiring place to write. Perched on Andover Lake, it was too cold to frolic outside but that was actually liberating. There was a rocking chair-ottoman combo in the master bedroom looking out on the lake and watching it freeze while I worked on some writing was so peaceful and perfect. When I needed to switch it up, there was a writer's desk with the same view and I can not overstate how nice and productive it was to work from it. I am sure in the summer it's a really fun stay (there were kayaks and a dock for swimming) but I actually loved being isolated in such an idyllic place. It's near a few other homes but the road was low traffic enough for a cold weather run around half the lake. Marcie was super helpful with suggestions for places to eat. We didn't actually use the recs - but that only speaks to how nice the house was and how hard it was to leave!

Home in Andover

What guests are saying

Close to Track-Saratoga Lake -Sunsets & Beach

4.83 out of 5 average rating, 29 reviews6 months ago

Absolutely beautiful and peaceful spot for our weekend get away! Perfect space for our family to relax and enjoy the area. The hosts were very accommodating and communicated well. We were in town to visit our son at RPI but wanted to try a different location and this one was awesome. We will be back and will plan to stay longer next time to enjoy the area even more.

Home in Saratoga Springs

What guests are saying

Couple's Lakeside Cottage, EZ access, Row Boat

4.93 out of 5 average rating, 27 reviews6 months ago

We had a great time! Jonathan was very responsive and answered every questions. Jonathan knew we were coming for fishing and since the weather was not cooperating he allowed us to check in earlier. His flexibility was appreciated by my husband who caught 3 huge bass the first day! The place is exactly how it is described. Perfect for a couple’s getaway. We enjoyed the scenery and felt relaxed and rejuvenated. Home is well stocked and clean. Great board game collection for fun evenings. Saratoga Springs is 35 minutes away for great restaurants and night life but plenty of local restaurant and pizzerias 10 to 15 minutes away. Overall great place with great host! We will definitely be back! Thank you again Jonathan for everything!

Cottage in Argyle

What guests are saying

The Lakeside, New Waterfront Home on Beach Pond

5 out of 5 average rating, 4 reviews1 month ago

The house was beautiful and scenery breathtaking. We loved watching the ice fishing, skating and go carting on the lake! We even went out on the frozen lake! It was close to my daughter’s home in Voluntown…. Only 4 minutes away! The kitchen was well stocked and we had everything we needed. They went above and beyond as we were there to celebrate my granddaughters’ first birthday! They left a gift for her and some welcome gifts for us too! Amazing!! They brought a table and chairs for extra seating!! Phil and Staci were amazing hosts and always responsive. We would definitely consider staying here again.

Home in Voluntown

What guests are saying

Swim, fish, kayak & RELAX!

4.93 out of 5 average rating, 27 reviews5 months ago

Carrie was very attentive and concerned about giving me the best instructions to make me feel at home. I didn't struggle to check-in and get settled. What ever question or concern I had she would answer me quickly and kindly. I recommend this beautiful place that will make you feel welcome and at home. Thank you for being an amazing host and being extremely caring, and sweet.

Cabin in Bethlehem

What guests are saying

WATERFRONT on the Hudson oasis🎒🛶🎣🔥Bring your boat!

4.89 out of 5 average rating, 56 reviews6 months ago

So, this space is an RV. I had never stayed in an RV, so there were a few things that I had to get used to. Firstly, the space is bigger than I had expected, which was a nice surprise. That said, the shower is incredibly tiny. Barely room to turn around, so be ready for that. The big difference is that this home is designed to be moved, so anything that can open and close has a very strong and sometimes complex locking system. Took a while to figure out how to open the fridge and the front door. Latches and doubly secure I assume so that nothing will open up while the home is in motion. The light switches are in odd places, the temperature control is a bit complex. Be sure to get clear instructions on using them. The RV has its own yard that is extremely well equipped. It's on a lovely creek. There's a gazebo and a fire pit and a swing, which are all nice additions for your stay.

Camper/RV in Saugerties

What guests are saying

Waterfront Cottage - HOT TUB & Fire Pit year-round

4.98 out of 5 average rating, 45 reviews1 month ago

We are two friendly couples that spent the weekend at Diana and Will’s house. The house is the perfect size for two couples or a family with kids. Everything was as described and Diana and Will were great hosts. They were very responsive and addressed any questions or issues that popped up in a timely fashion. We would recommend this spot for anyone looking for a break from big city life!

Home in Lake Katrine

What guests are saying

Waterfront Cabin close to Lake George & Saratoga

4.93 out of 5 average rating, 75 reviews7 months ago

Mary's home was everything we hoped for. Her property was beautiful and serene. Stepping out into the back yard every morning to view the river over a hot cup of coffee was a wonderful way to start each day. There were many water activities available on the property for us to enjoy such as kayaks, tubes, and canoes, but it was also very cozy and relaxing enough just to sit in the yard and just enjoy the property. Firewood was also available. Everything we needed was already at the house (even board games), and the house was clean and tidy. Mary was available for any questions, if needed. My family and I plan on returning to Mary's property in the future. We are very thankful to have found Mary's place.

Cabin in Lake Luzerne

What guests are saying

Lakeshore Cabin with boat dock

5 out of 5 average rating, 16 reviews6 months ago

What a gorgeous place! As other guests have noted, the photos just don’t do it justice. October is the perfect time to sit on the dock with some coffee and take in the fall foliage.. The house is super cute and well appointed, I think it might be the best stocked kitchen of any Airbnb I’ve stayed in. Lots of lovely plates and glasses and festive little napkins and towels. This was a mom/daughter girls weekend, and everyone was impressed with the toiletries in the bathroom. The house was super clean and the beds were comfy, we can’t wait to go back!

Cabin in East Haddam