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Holiday rentals with a kayak in Hampden County

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Top-rated rentals with kayak in Hampden County

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.

4.98 out of 5 average rating, 104 reviews
Top guest favourite
A charming cottage is set amidst colorful autumn foliage, with a gravel driveway leading up to the entrance. Large windows allow natural light to enter, while a wooden deck is visible at the side, showcasing a welcoming outdoor area with surrounding greenery.
Cottage in Wales

Sunset and Sunrise views at this lake cottage.

Ready to relax and have fun! Just bring your clothes, everything else is here at this cottage named Tramonto Sul-Lago – Sunset over lake. You and up to 5 guests will enjoy all amenities! You won’t want to miss sunrise either, it creates reflections of nature on the water. Grab a kayak and go for a paddle, set up a yard game, head to the dock with a fishing pole, pull up some chairs to the fire pit (firewood provided). The back yard is a private oasis. Winter offers skating and ice fishing!

4.97 out of 5 average rating, 76 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

4.98 out of 5 average rating, 167 reviews
Top guest favourite
A charming blue cottage is depicted, featuring a welcoming yellow front door and large windows. A stone pathway leads to the entrance, surrounded by natural landscaping. Tall pine trees offer shade, while a white picket fence encloses the property.
Home in South Hadley

Charming Riverfront Cottage

Charming 2 bedroom, 1 bathroom cottage on a peaceful cove of the Connecticut River. Enjoy bird life, water views and magical sunsets in this nature lovers’ paradise. Bright and airy throughout. Fully equipped kitchen. Two bedrooms on the first floor, with a loft space upstairs with a futon couch/bed. Two TV's (Roku). We've provided 2 touring kayaks (longer/heavier than other kayaks) in the shed. We recommend at least one strong person and bring water shoes (the bottom is yucky)!

5.0 out of 5 average rating, 74 reviews
Superhost
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.

4.84 out of 5 average rating, 141 reviews
Top guest favourite
A modern two-story house with large triangular windows is set against a twilight sky. The elevated structure features a spacious deck wrapped with a railing, providing outdoor seating options. The ground level showcases garages, and soft lighting highlights the exterior architecture.
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

4.91 out of 5 average rating, 110 reviews
Top guest favourite
A quaint lakeside cottage features large windows for scenic views and a deck with outdoor seating. A grill is positioned nearby for easy outdoor cooking. The property is framed by lush greenery, enhancing the natural setting by the water's edge.
Home in Becket

Cozy lakehouse

Relax with family or friends at this sweet cottage on Center Lake in the Berkshires. This lakeside cottage is charming and rustic. Enjoy a beautiful day on the lake swimming, fishing off the dock and kayaking. Grill dinner on your private deck and watch the stars come out in the evening Or enjoy all that the Berkshires have to offer, Jacob’s Pillow (15 min), Berkshire Theater (20 min), Tanglewood (30 min). There are plenty of nearby hiking trails and charming towns to explore.

5.0 out of 5 average rating, 116 reviews
Guest favourite
Home in Stafford

Serene Lakefront Retreat

This idyllic 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake accommodates up to 6 guests (4 beds), offering an unforgettable experience for your family. Enjoy breathtaking views from the cozy living area or the private deck. Kayak (2 included), swim off the floating dock, stargaze, grill out and enjoy your coffee on the deck! Separate workspace and free Wi-Fi for those working from home. Perfect for Brimfield Antique attendees. Book now for a relaxing getaway!

4.93 out of 5 average rating, 107 reviews
Guest favourite
A wooden deck offers high-top chairs facing a tranquil lake surrounded by trees. The scene includes a spacious grassy area leading to the water, with a gazebo visible in the distance. A gentle mist adds a serene quality to the landscape.
Home in Union

Antique Home w Private Pond, Sturbridge /Brimfield

Minutes to Sturbridge, great craft breweries, (including TreeHouse), Brimfield Antique Flea Market. Our recently ( and ongoing) renovated 1800s farm house is ready for your next stay. It is quirky and not for perfectionists! Visit nearby Old Sturbridge and its many great shops and restaurants, and nearby State Parks. Plenty of room, fully equipped kitchen, comfy living rm & big dining room. 3 comfortable bedrooms upstairs. Very easy off/on the highway to be on your way quickly!

4.83 out of 5 average rating, 162 reviews
Guest favourite
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.
Cabin in Otis

Berkshires Lakefront Boho Modern Retreat

Welcome to Watson Pond Lodge in the Berkshires. This beautiful lakefront contemporary 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.

4.96 out of 5 average rating, 25 reviews
Top guest favourite
A private outdoor patio area features a round table surrounded by four chairs, positioned on a brick surface. A swing chair is visible nearby. The peaceful lake view extends beyond, framed by trees and rolling hills under a bright blue sky.
Cottage in Holland

Cozy Lakefront Cottage

Welcome to our rustic, seasonal cottage on the lake. Perfect for couples or friends looking for a quiet getaway, or small families w/kids beyond toddler age. Newly renovated. Clean & comfortable. Use of the entire cottage, including; 2 bedrooms, well equipped kitchen, comfortable living room w/flat screen TV & DVD player, screened in porch, private outdoor patio & small beach area w/dock, & 3 kayaks. Centrally located near Sturbridge w/easy access to I-84 & MassPike.

4.96 out of 5 average rating, 101 reviews
Guest favourite
A cozy house is framed by tall trees, with a snow-covered landscape surrounding it. The exterior features a combination of warm wooden siding and a brick chimney. A large screened porch is visible, offering a seamless connection to nature.
Home in Holland

D. Chief's Lodge Cheerful Cabin at the Camp

Year round house: you'll have a great time at this comfortable place to stay. Camp Mishnoah, a former Girl's Club Camp, is undergoing restoration into a wellness retreat. This rental is a stand alone house. A very comfortable queen size bed and a single bed in a separate bedroom, lodge style living room with a vaulted ceiling, full kitchen, bathroom with shower and a half bath. Access to the pond and hiking trails. Nearby Sturbridge Village and Tree House Brewery.

4.91 out of 5 average rating, 123 reviews

Popular amenities for kayak rentals in Hampden County

KitchenWifiFree parking on premisesAir conditioning

House rentals with a kayak

Top guest favourite
An aerial view of a lakeside home surrounded by trees showcasing fall foliage. A wooden dock extends into the calm water, with the house positioned amidst lush greenery. The vibrant autumn colors add warmth to the natural setting.
Home in Becket

Fall Foliage Lakefront Retreat - Berkshires

5.0 out of 5 average rating, 46 reviews
Guest favourite
A spacious cabin is surrounded by lush greenery and features a wooden deck with outdoor seating. A hot tub is located on the deck, overlooking the yard. A stone fire pit is centered on the lawn, with a gravel driveway leading to a detached garage.
Home in Tolland

Cabin with Hot Tub and Lake Access

4.9 out of 5 average rating, 20 reviews
Top guest favourite
A spacious deck is depicted, featuring comfortable seating and an umbrella for shade. The railing offers unobstructed views of a tranquil lake, surrounded by lush greenery. A private dock is visible in the distance, inviting outdoor activities.
Home in Brimfield

Little Alum-Lakefront Home

4.96 out of 5 average rating, 24 reviews
Top guest favourite
A spacious wooden deck features two comfortable Adirondack chairs facing the tranquil lake. Lush trees surround the area, providing shade and a natural setting, while the calm water glimmers through the foliage.
Home in Tolland

Lakefront Retreat at Porcupine Place

5.0 out of 5 average rating, 46 reviews
Top guest favourite
A charming lakefront cabin is seen from the front, surrounded by a well-maintained yard with green grass and a gravel driveway. Tall trees and shrubs provide a natural border, while the serene lake is visible in the background, enhancing the peaceful setting.
Home in Wales

Charming water front cabin with boat dock

4.98 out of 5 average rating, 64 reviews
Guest favourite
A modern single-story home is framed by a vibrant red bush and manicured lawn under an orange and pink sunset sky. The house features a chimney, inviting entryway, and accessible garage, creating a welcoming exterior.
Home in Blandford

Relaxing Home nestled in Rural Hilltown

4.86 out of 5 average rating, 93 reviews
Guest favourite
The image captures a serene view of the lake with calm waters reflecting the surrounding greenery. A private dock and various boats are visible, enhancing the outdoor atmosphere. Lush trees frame the scene, providing a natural backdrop to this tranquil lakeside setting.
Home in Holland

Cozy Lake Retreat | Halloween Decorated Getaway

4.95 out of 5 average rating, 20 reviews
Guest favourite
The tranquil lakefront view showcases a private dock with a boat moored alongside, surrounded by lush greenery. The calm water reflects the surrounding trees and sky, creating a serene atmosphere perfect for relaxation. A well-maintained landscape features flower beds and stone pathways leading to the dock.
Home in Holland

Holland MA - Pet friendly Lake Home!

4.89 out of 5 average rating, 35 reviews

Cottage rentals with a kayak

Top guest favourite
A bright, open living area features large glass sliding doors that overlook the lake. A dining table surrounds by chairs is set in the foreground, with a comfortable seating area visible to the right. Bookshelves and a decorative rug add warmth to the space.
Cottage in Otis

Berkshire lakefront cabin with modern luxuries

4.98 out of 5 average rating, 93 reviews
Guest favourite
A serene lake view is framed by lush green trees, with the calm water reflecting the clear blue sky. A private dock extends into the lake, providing access to kayaks and paddle boards. Nearby buildings are visible along the shoreline.
Cottage in Holland

Hamilton Cottage | Cozy Lakefront A-Frame

4.97 out of 5 average rating, 35 reviews
Superhost
A sandy beach area is revealed, bordered by gentle waves lapping at the shore. Several lounge chairs are positioned for relaxation, with green trees framing the scene. The expansive lake stretches into the distance, under a partly cloudy sky.
Cottage in Suffield

The Congamond Cottages: Private Lakefront Cottage

4.86 out of 5 average rating, 57 reviews
Guest favourite
Two Adirondack chairs are positioned near a fire pit, surrounded by decorative stones and tree stumps. A view of the sparkling water and nearby houses can be seen in the background, framed by lush green trees that enhance the peaceful outdoor setting.
Cottage in Holland

Blissfully Peaceful Cottage nestled on lake

4.93 out of 5 average rating, 57 reviews
Guest favourite
Cottage in Becket

Cozy Cottage-Sunset On the Lake!

4.79 out of 5 average rating, 63 reviewsA 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

Lakefront | Pvt Dock | Kayaks | Firepit | 1G | W/D

4.93 out of 5 average rating, 292 reviews
Guest favourite
The cottage is situated on a hill, surrounded by lush greenery. A wooden deck extends from the front, offering views through large windows. The natural landscape includes vibrant plants and foliage, complementing the cottage's inviting exterior.
Cottage in Holland

Quiet Cottage with Beautiful Views!

4.87 out of 5 average rating, 67 reviews
Top guest favourite
Cottage in Otis

Cozy Berkshire Cottage

5.0 out of 5 average rating, 8 reviews

Cabin rentals with a kayak

Guest favourite
Cabin in Becket

Berkshires! Walk to LAKE, kayaks, dog friendly.

4.92 out of 5 average rating, 53 reviews
Guest favourite
The open living space showcases a vaulted ceiling with exposed beams and a stone fireplace. Light wooden cabinets and countertops create a warm ambiance. Two seating areas include a cozy couch, a reclining chair, and a patterned rug, inviting relaxation and conversation.
Cabin in Otis

Enjoy 43 Acres on Two Ponds!

4.89 out of 5 average rating, 70 reviews
Guest favourite
Cabin in Wilbraham

4BR Lakefront Cabin with Private Dock & Beach

5.0 out of 5 average rating, 5 reviews
Cabin in Westhampton

Lakefront Westhampton Cabin w/ Beach + Kayaks!

4.93 out of 5 average rating, 14 reviewsThe log cabin sits nestled among tall trees on a green, expansive lot. A stone pathway leads to the entrance, flanked by neatly trimmed shrubs. A screened porch is visible, enhancing the connection to the natural surroundings.
Cabin in Otis

Cozy Cabin Retreat in the Berkshires

4.24 out of 5 average rating, 17 reviewsA calm lake scene is depicted in the early morning light, with a person seen kayaking through a layer of mist. The dock is visible in the foreground, providing a serene connection to the tranquil water surrounded by lush greenery.
Cabin in Wilbraham

Lakefront Cottage w/ Fireplace, Dock & Home Office

4.65 out of 5 average rating, 49 reviews

Destinations to explore