Holiday rentals with a kayak in Massachusetts

Find and book unique kayak rentals on Airbnb

Top-rated rentals with kayak in Massachusetts

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

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Top guest favourite

Cottage in Brimfield

Cheerful cottage by Little Alum Lake & Sturbridge

Little Alum is a gorgeous spring-fed lake in the quintessential New England town of Brimfield, MA. Brimfield is known as home to the largest flea market in the country. Little Alum is regarded as one of the cleanest lakes in Massachusetts due to its pristine water quality. The charming cottage is a one level home within close proximity to highways & downtown Sturbridge and off route 20 just a few minutes to downtown Brimfield and Antique show/flea market. Partial water views, steps to the water.

Outdoor spacesLocationSleep quality

4.98 out of 5 average rating, 109 reviews

Guest favourite

A charming two-story house is nestled by the water, featuring a wraparound deck adorned with seating. The landscaped yard includes rocky pathways and a small gathering area with Adirondack chairs, inviting moments of relaxation by the water's edge.

Home in Sturbridge

Lake Front Home Sleeps 6-8 on a private Peninsula!

Stunning year-round waterfront home on its own private peninsula—sleeps 6–8 with 3BR/2BA, a spacious living room with sliders to a wraparound deck, and a heated sun porch offering panoramic lake views. Nearly every window overlooks the water. Outside, enjoy a private dock, new stone patio & firepit, small beach area, kayaks, canoe, and rowboat. Perfect for families, couples, or a friends’ getaway. See walkthrough videos at on YouTube @CedarLakeCottage Summer: 4-night min | Holidays: 3-night min

LocationValueTV

4.94 out of 5 average rating, 332 reviews

Guest favourite

A lakefront cottage is positioned among trees, with a spacious lawn leading down to the water. A newly installed dock extends into the lake, while various colorful kayaks and paddle boards are neatly arranged on the grass. The sun sets, casting a warm glow over the scene.

Home in Westminster

Lakefront, view of ski mtn, fireplace, sauna

Direct lakefront with panoramic views of Wachusett Mountain (#1 skiing in MA). In the summer, enjoy the kayaks, canoe, paddle-boards, motor boat. In the winter, cozy up next to the fireplace and enjoy a complimentary bottle of wine. In the fall, gaze upon the breathtaking foliage from the sunroom. Outdoor shower, dock, firepit, hammock, bike, washer/dryer, desk, sauna, dishwasher, linens, kitchen amenities. Our other lakefront house is down the road: www.airbnb.com/h/lakefrontmountainview

ValueOutdoor spacesTV

4.89 out of 5 average rating, 242 reviews

Top guest favourite

A view of the calm water on Mirror Lake is framed by a flower-lined, stone patio leading to a wooden dock. The water reflects the greenery from the surrounding trees under a clear blue sky.

Home in Wrentham

Relaxing Waterfront Lakehouse, 10 min to Gillette

Relax at this peaceful, family-friendly lake house on Mirror Lake. Fully renovated 3-bedroom, 2 full bath getaway directly on the water with private deck, dock, patio area, propane grill, paddle boards, kayak, fishing, and more. Located nearby Gillette Stadium, Patriot Place, Wrentham Premium Outlets, Plainridge Park Casino, an abundance of restaurants, wedding venues, walking trails and central to Boston or Providence, this is a great location for many activities or just lounging by the water.

ValueLocationHospitality

4.96 out of 5 average rating, 110 reviews

Top guest favourite

A calm lake reflects vibrant autumn foliage, with trees displaying shades of red, orange, and yellow. A boat is anchored near a wooden dock, and the surface of the water mirrors the colorful landscape, creating a serene and picturesque scene.

Cottage in Becket

Berkshires Cottage by Lake. Year Round Adventures.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX. (90 second walk through wooded path to lake) Pets Considered. $29. pet fee = approved Pet Agreement.

LocationValueQuiet

4.95 out of 5 average rating, 325 reviews

Top guest favourite

A hot tub with bubbling water is showcased under a covered patio, offering a view of the serene lake and surrounding trees. Soft lighting enhances the tranquil setting, while glimpses of the lake's shoreline and distant boats are visible in the background.

Cottage in Southwick

Lake Views from Deck Fire Pit & Hot Tub 4 Kayaks

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 a week long getaway with 2 work spaces. 25 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

Outdoor spacesLocationAir conditioning

4.98 out of 5 average rating, 171 reviews

Top guest favourite

Cottage in Mendon

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

Welcome to our charming 3-bedroom lake cottage in Mendon, MA, where every sunrise paints the sky with breathtaking hues over tranquil waters. Accommodates 6 guests, making it ideal for families or couples seeking serenity. Enjoy lakeside coffee, fishing, kayaking, and evenings by the fire pit. We are pet-friendly, so feel free to bring your dogs along — if you have more than 1 dog, please let us know. Conveniently located near restaurants and attractions. Book now for a magical getaway!

Outdoor spacesValueAmenities

4.96 out of 5 average rating, 160 reviews

Guest favourite

A contemporary cedar home is set on a spacious green lawn surrounded by trees. The two-story structure features a large front porch and a combination of wooden and glass elements, enhancing its integrated design with nature. A gravel pathway leads to the entrance.

Cabin in Becket

Wildlife Retreat in the Forest

Home in the Birkshires! 12 minutes away from Jacob's Pillow, 2.5 hours away from NYC. Our Beautiful Lindal Cedar Contemporary home has everything you'll need. It is tucked away on a private 9+ acre estate with 4 large bedrooms, 2.5 baths. The Master Bedroom can be your own private getaway with 2 balconies. One overlooks the large living room with floor to ceiling windows and stone fireplace. The other overlooks the expansive property. It's definitely a tranquil place to rest and relax.

ValueLocationKitchen

4.84 out of 5 average rating, 143 reviews

Guest favourite

A firepit area is surrounded by several light blue chairs, set on a pebbled ground. The calm lake reflects the trees and landscape, creating a serene outdoor space ideal for gathering and relaxation.

Cottage in Becket

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

LocationOutdoor spacesAmenities

4.92 out of 5 average rating, 302 reviews

Top guest favourite

A spacious living area is highlighted by a high wood-paneled ceiling and large windows allowing natural light. A stone fireplace is centrally located, complemented by comfortable seating and a wooden coffee table on a light-colored rug.

Home in West Brookfield

Peaceful Lake Escape w/ Porch, Fire Pit & Kayak

Escape to this charming West Brookfield lake retreat! This 3BR, 2BA home sleeps 8 and features 1,700 sq ft of open-concept space, a wraparound porch, and an outdoor fire pit. Enjoy walking access to the lake and cozy evenings under the stars, perfect for families and friends seeking a classic New England getaway. Salem Cross Inn - 3min drive Lake Wickaboag - 5min walk West Brookfield Town Common - 5 min drive Rock House Reservation - 10 min drive Brookfield Orchards - 10 min drive

ValueLocationFamily

4.91 out of 5 average rating, 114 reviews

Top guest favourite

A light-filled living area features a pull-out sofa adorned with striped cushions and a coffee table with a decorative book and lamp. A sliding glass door opens to a sleeping area with a spacious bed, while bright curtains frame the window, offering a view of the exterior.

Guest suite in Marblehead

Ocean Park Retreat

Bright and cheery 1 bedroom ground floor apartment with two+ car parking on quiet street in Marblehead's Ocean Park neighborhood, just steps from the ocean. Full size bed and pull-out full-size sofa in living room, private bathroom with in-floor heating, kitchenette with microwave, dishwasher, sink, double induction cook-top, refrigerator, and toaster oven. Laundry access. Walk to the waterfront, watch the sailboats drift by. Fifteen- minute walk to Historic town center.

ValueOutdoor spacesCheck-in

4.91 out of 5 average rating, 324 reviews

Top guest favourite

A game area features a colorful 'Roll and Score' arcade game highlighted by vibrant blue lighting. The background displays a large Boston Red Sox-themed mural, enhancing the playful atmosphere. Beside the arcade game, a shuffleboard table contributes to the entertainment options available.

Home in Harwich

* Game Room, Linens, Quiet St, Central AC/Heat

Cape Cod - Harwich/Dennis Line - Entire Home, 6 Beds + Futon (4 Bd/2 Ba), Includes 2 King Beds, Seasonal Outdoor Shower, Linens Included! Central A/C, Game Room, Cable, Wifi, Pet-Friendly, Near Beaches, Golf, Shopping & Attractions. Great Central Location at CapeVaca. Nearby Beaches: Mayflower, Earle, Pleasant Road, Corporation, West Dennis, Crowe's Pasture, Paines Creek, Harwich, Dennis, Brewster. Message us for early check-in options during the off-seasons.

ValueOutdoor spacesHospitality

4.98 out of 5 average rating, 179 reviews