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Vacation rentals with a kayak in Massachusetts

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Top-rated kayak rentals in Massachusetts

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

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Top guest favorite

A serene lakeside view captures a vibrant sunset with the sun partially descending behind distant hills. A lone fisherman in a boat is visible on the water, while a wooden deck features seating arrangements surrounded by lush plants.

Guest suite in Tyngsborough

4.98 out of 5 average rating, 244 reviews

Lakefront Suite Two-Room, Comfy, Tranquil

Located on a lovely small lake with a panoramic view from the bedroom, private spa-like bathroom, cotton linens, a comfy bed, A/C and a living room-so not an 'entire' home but more than just a room! Quietly watch lake nature or boats going by, or choose to swim, kayak, or fish. Enjoy industrial history at Lowell's National Park mills, take a forest walk nearby, or drive 10 min. to Nashua for its many restaurants and tax-free shopping. 1 hr from Boston and near many New England highlights.

Top guest favorite

A spacious wrap-around porch is shown with comfortable seating, offering panoramic views of the waterfront. The warm glow of sunrise reflects on the water, and a distant bridge is visible under a clear sky. The setting invites relaxation and enjoyment of the serene environment.

Home in Somerset

5 out of 5 average rating, 128 reviews

Beachfront W/ HotTub,Sauna, Pool & Panoramic view

Welcome to the Heart of Somerset! Nestled at the very tip of Somerset on a private dead-end road, this coastal waterfront home is the perfect place for a family retreat, romantic getaway or friends seeking adventure Marvel at the panoramic views and dramatic colors from Sunrise to Sunset of the Braga Bridge, Mt. Hope Bridge & Bay, Bristol, Tiverton Rhode Island & the Fall River cityscape on the horizon. Grab a kayak or relax, soak up the sun & let the gentle sea breeze wash your worries away!

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

4.94 out of 5 average rating, 203 reviews

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 • 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

Top guest favorite

Cottage in Yarmouth

5 out of 5 average rating, 217 reviews

Serenity Views | Waterfront | KingBed | Kayaks SUP

Enjoy our cottage's charm and comfort with panoramic views and abundant sunlight. Comfortably hosts 2 families. Wake up to incredible sunrises. Lounge on the hammock or swim/fish/kayak in our beautiful backyard waterfront Long Pond. Explore the Cape in each direction: beautiful beaches and endless fun activities/interests. At the end of the day, enjoy dining on the deck as you grill. Sit back on the patio with a cocktail and gaze at the star filled sky and ambiance from the fire table. Welcome!

Top guest favorite

The cottage exterior is illuminated by warm lights, showcasing a spacious deck with inviting seating. Lush greenery surrounds the property, with a vibrant purple flowering bush nearby. The serene atmosphere is enhanced by the evening sky, providing a cozy and welcoming retreat.

Cottage in Marion

4.99 out of 5 average rating, 166 reviews

Little Boho Retreat by the Beach

Kick back and relax in the most calming, low charm country, coastal cottage the town of Marion has to offer. You’ll experience spectacular view of the beach right from the deck to watching the boats from the harbor. Don’t just limit yourself to life at the beach in just the summer months, come and make memories in this beautiful year-round cozy cottage. It's a perfect retreat to go swimming, kayaking, fishing, bird/seal/crabs watching and more right here in a private community on Dexter Beach.

Top guest favorite

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

4.98 out of 5 average rating, 108 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

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, 154 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!

Top guest favorite

A view from a window showcases vibrant pink and white flowers in window boxes, framing a serene lake scene. Beyond the flowers, the calm water reflects the gentle colors of the sky, while white Adirondack chairs are positioned on a deck that extends over the pond.

Guesthouse in Plymouth

4.94 out of 5 average rating, 124 reviews

Charming Pond-Front Boathouse

Charming antique boat house located directly on Long Pond. Quiet, peaceful accommodations with 180 views. Watch the American Bald Eagles and Osprey search for fish at dusk from your private deck that reaches out over the pond. Long Pond is full recreation, two kayaks and a canoe are available. Hiking, bicycling, golfing, fishing, swimming, boating, snorkeling, sunbathing, and napping are just a few of the activities that can be enjoyed in the quaint, semi-private, pond-front accommodation.

Two colorful kayaks are positioned on a concrete dock, with the calm waters of the bay extending into the distance. The sky above is clear with some soft clouds, reflecting a tranquil outdoor setting.

Cottage in Westport

4.9 out of 5 average rating, 105 reviews

Kayaks and Glimpses of Westport Bay

Stay in a lovely and comfortable cottage with partial views of the bay. The water is just a short walk away past our neighbor with shared access to the water. Enjoy swimming, fishing, or relaxing on the float and soak up the sun. You can also explore the Horseneck Beach, wander the trails, taste the local farms and restaurants, and more. If you want to unwind at the cottage, watch shows on the 65" Samsung Smart TV, fast Wi-Fi, sit on the deck, and flip some burgers on the gas grill.

Top guest favorite

A tranquil scene captures a couple seated on a dock, surrounded by tall green grasses. The calm water reflects soft hues of pink and blue from the sunset, creating a serene backdrop of trees across the pond.

4.96 out of 5 average rating, 196 reviews

Lakefront House/Private Dock/Year Round Hot Tub/AC

Beautiful cottage nestled on a half-acre of waterfront property on Swan Pond. The dock offers direct water access. Available are two kayaks, a canoe and two paddleboards. The kitchen offers beautiful views of the water while you enjoy your morning coffee. Local beaches are just minutes away. Enjoy the hammock, swings, hot tub, grill, outdoor fire pits and cocktails on the deck. Wanderers' Rest is located close to bike trails, boat rentals, movie theaters, restaurants, and bars.

Cottage in Orange

4.91 out of 5 average rating, 182 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.

Top guest favorite

An outdoor seating area is situated alongside the river, featuring four cushioned chairs arranged around a fire pit. An adjacent table complements the space, with lush greenery in the background and a grill visible nearby. The tranquil river view creates a peaceful atmosphere.

4.98 out of 5 average rating, 171 reviews

Sunrise on the Water's Edge - Riverside Bungalow

Cozy riverside bungalow celebrates panorama views of the peaceful Connecticut River. Multiple levels of outdoor living space, open-air and screened-in. Just minutes from all major points of interest in the Pioneer Valley - including Six Flags New England, MGM Casino Complex, Big E Fairgrounds, Basketball Hall of Fame, and the Greater Springfield Metro area. Only 20 minutes from Bradley International Airport (BDL) in Windsor Locks.

Vacation rentals for every style

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Convenient locations with everyday essentials

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Quaint homes, peaceful surroundings

Popular amenities for Massachusetts kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Top guest favorite

A wooden outdoor table and benches are positioned on a stone patio, overlooking a serene pond. Lush greenery lines the water's edge, and white flowers in a planter enhance the natural setting. The calm water reflects the surrounding trees and sky.

Home in Yarmouth

5 out of 5 average rating, 305 reviews

gorgeous waterfront cottage w/4kayaks and 2 SUPs

The exterior of the house showcases a wooden facade framed by lush greenery. A large wooden deck extends from the back, furnished with chairs, ideal for relaxation. Sunlight filters through the trees, highlighting the serene outdoor space.

Home in Yarmouth

4.88 out of 5 average rating, 153 reviews

* Walk to the beach - Swiss Beach House! *

Several colorful kayaks are lined up on a grassy area near a tranquil lake. A wooden dock extends into the water, surrounded by lush trees. A park bench offers a comfortable spot to relax and enjoy the serene natural setting.

4.94 out of 5 average rating, 148 reviews

Lake front retreat - Stylish Berkshire home

A spacious deck features a glass-top table and a blue Adirondack chair overlooking the river. The warm glow of the sunset reflects off the water while trees provide a serene backdrop, creating a peaceful outdoor space.

Home in Westport

4.96 out of 5 average rating, 28 reviews

Riverhouse

A serene view of a sandy beach leading to calm waters. The lake stretches into the distance, bordered by green trees along the shoreline, under a clear blue sky. A floating dock is visible in the water, inviting outdoor activities.

Home in Mashpee

4.92 out of 5 average rating, 139 reviews

Cape Cod; John’s Pond beach w/2 kayaks -SuperHost!

A grassy outdoor space features two blue Adirondack chairs and a small fire pit, surrounded by trees and overlooking a serene pond. A hammock hangs in the distance, while the deck is visible on the right, extending from the house.

Home in Oak Bluffs

4.83 out of 5 average rating, 193 reviews

Waterview, Private, Walk to Beach, Mile to Town

An open-concept living area features a comfortable sectional sofa, wooden coffee table, and bright skylights allowing natural light to fill the space. A modern kitchen with a large island and bar seating complements the airy atmosphere, providing a seamless flow to the dining area and views outside.

4.96 out of 5 average rating, 109 reviews

Direct Lakefront Home on Otis Reservoir Giant Yard

A wooden dock extends into a serene freshwater pond, surrounded by lush green foliage. The calm water reflects the clear blue sky and distant tree line, creating a tranquil setting for relaxation and outdoor activities.

Home in Brewster

4.87 out of 5 average rating, 208 reviews

Water Front Pond House - 3 acre Cape Cod Sanctuary

Cottage rentals with a kayak

Top guest favorite

The interior space features warm wood paneling with vaulted ceilings and exposed beams. A cozy living area showcases a kitchen bar with seating, while two bedrooms are visible in the background. Natural light streams in through skylights and windows, creating a bright atmosphere.

Cottage in Dennis

4.94 out of 5 average rating, 114 reviews

Compass Rose Cottage ★ Steps to Flax Pond & Trails

Cottage in Dennis

4.98 out of 5 average rating, 179 reviews

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

A cozy living area is highlighted by a navy blue sofa adorned with decorative pillows. The light wood floor complements the bright blue walls, while a flat-screen TV and a coffee table with remote sit within the space. Natural light filters through large glass doors, overlooking a private patio.

Cottage in Yarmouth

4.92 out of 5 average rating, 471 reviews

MODERN COTTAGE W/ BIKES, PADDLE BOARDS & KAYAKS

A bright living area features wooden beams across the ceiling and light walls. A comfortable couch with decorative pillows faces a coffee table stacked with magazines. Two lamps provide ambient lighting, while sunlight enters through multiple windows, creating a welcoming environment.

Cottage in Falmouth

4.94 out of 5 average rating, 170 reviews

“Cozy Cottage” on Great Bay

Cottage in Dennis

4.97 out of 5 average rating, 115 reviews

Local Beach+ Fireplace + Hot Tub Under the *Stars*

Top guest favorite

A serene lake reflects the colors of twilight, with calm waters mirroring the darkening sky. A crescent moon is visible, while silhouettes of trees line the horizon. The scene captures the tranquil beauty of dusk over the peaceful landscape.

Cottage in Hinsdale

4.99 out of 5 average rating, 153 reviews

Cozy Cottage in the Berkshires

The exterior of the condo duplex is showcased, featuring a shingle-style façade, a welcoming porch with a white door, and large windows. Lush greenery, including shrubs and a small tree, surrounds the entrance, enhancing the inviting appearance of the property.

Cottage in Brewster

4.82 out of 5 average rating, 11 reviews

Cottage near bay beach- 1 Bd/1Ba

The spacious deck is softly illuminated by string lights during the evening, creating a cozy atmosphere. Seating areas are arranged around a fire table, with surrounding greenery and potted plants enhancing the outdoor setting. A nearby building is partially visible in the background.

Cottage in Dennis

4.95 out of 5 average rating, 100 reviews

The Lemon Drop Cottage- Swan Pond River Views!

Cabin rentals with a kayak

Top guest favorite

A cozy sunroom features two spacious daybeds adorned with soft blankets and cushions, positioned beside large windows that offer serene views of the pond. Natural light floods the room, highlighting wooden walls and a unique stained glass window at the peak of the ceiling.

4.97 out of 5 average rating, 70 reviews

Panoramic Sunroom | Soaking Tub | Modern Cabin

Top guest favorite

A view of the cabin and neighboring house is presented, surrounded by trees. The yard is partially covered with fallen leaves, revealing patches of green grass. A gravel driveway leads towards the entrance, providing access to the property.

Cabin in Webster

4.93 out of 5 average rating, 165 reviews

The Camp

A log cabin is surrounded by tall trees and lush greenery, situated on the shore of a tranquil lake. A wooden dock extends into the lake, with two kayaks and a rowboat visible nearby, offering a serene setting for relaxation.

Cabin in Groton

4.96 out of 5 average rating, 24 reviews

Secluded Rustic Lakeside Cabin - Perfect Escape

The exterior of a contemporary wooden home is presented, highlighted by large window features and a distinctive A-frame roof. Surrounding greenery includes a well-maintained lawn and various shrubs, creating a natural setting. A garage is visible to the left, providing easy access.

Cabin in Becket

4.86 out of 5 average rating, 112 reviews

Wildlife Retreat in the Forest

A round wooden dining table is accompanied by four light-colored chairs, positioned near large windows. The views of lush greenery and the lake are visible through the windows, creating a bright and inviting space.

Cabin in Douglas

4.89 out of 5 average rating, 9 reviews

Rustic Log Cabin on the Lake

A comfortable sofa is positioned near a window with sheer curtains, allowing natural light to illuminate the space. A decorative pillow with text is placed on the sofa, while a glass of wine rests on a wooden table outside, visible through the window.

Cabin in Winchendon

4.96 out of 5 average rating, 45 reviews

The little house on Mirror Pond

The log cabin exterior features a spacious deck with several lounge chairs positioned for relaxation. A stone wall adds texture to the wooden structure, while stacks of firewood are neatly arranged on the side, surrounded by natural greenery.

4.89 out of 5 average rating, 53 reviews

Enjoy 43 Acres on Two Ponds!

A cozy fire pit area is surrounded by multiple wooden chairs, inviting relaxation. The serene lake reflects the surrounding trees and colorful autumn foliage, adding to the peaceful setting. The lush green grass blends effortlessly with the natural landscape.

5 out of 5 average rating, 4 reviews

Berkshires Lakefront Boho Modern Retreat

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