Vacation rentals with a kayak in Hampden County

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Top-rated kayak rentals in Hampden County

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Top guest favorite

A decorative wooden tray is displayed on a table, featuring the words 'Guest Cottage' and 'Make Yourself at Home.' A silver pitcher holds a bouquet of pale pink peonies, adding a touch of elegance to the inviting setting. Natural light filters in through nearby windows.

Cottage in Brimfield

4.99 out of 5 average rating, 77 reviews

Cheerful 2 bedroom cottage with lake access.

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.

Top guest favorite

Two black Adirondack chairs are positioned on a wooden deck, facing a serene lake surrounded by lush green trees. A small circular table sits between the chairs, offering a perfect spot for relaxation while enjoying the tranquil water views.

Cottage in Otis

4.98 out of 5 average rating, 64 reviews

Berkshire lakefront cabin with modern luxuries

Be one of the first to rent this newly renovated, 3 bedroom, 2 bath, lake front cabin with hot tub and modern amenities on Massachusetts' largest recreational lake. Enjoy sunset views from the tricked-out, oversized deck that offers dining, grill and fire table. A state forest is your neighbor, offering miles of trails, hiking and waterfalls. Use our kayaks, swim from one of 2 docks, or bring your own boat/jet ski. 25 minutes from all major Berkshire attractions, this is lake life at its finest.

Top guest favorite

A canoe glides smoothly on the lake's calm surface, with three individuals seated inside. Lush greenery and a charming wooden dock are visible in the background, enhancing the serene lakeside setting.

Home in Belchertown

4.98 out of 5 average rating, 85 reviews

Moonstone Lake House – romantic, serene, fun!

Lake Holland has cleared beautifully after an algae overgrowth. Tho still closed for swimming as of 8/8, the town beach at Lake Arcadia is minutes away with 4 person paddle boats too. We offer: - a fire pit/grill feet from lake - huge deck - fresh herb planter - 3 kayaks - (1 ) 3-person canoe - cozy propane wood stove inside - fully equipped kitchen - hiking - museums Note: our home close-by separated by a tall screening fence. DOG LOVER? Please scroll to "Other Details to Note”

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, 126 reviews

Hot Tub w/ Foliage Lake Views, Fire Pit & 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 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

Guest favorite

A decorative sign featuring an anchor design and the text 'Luke & Ali Riverfront' is displayed prominently. The sign is octagonal and metallic, contrasting with the lush green landscape in the background.

Guest suite in South Hadley

4.85 out of 5 average rating, 106 reviews

River front guest suite

Unique 2 bedroom guest house on the Connecticut River in South Hadley, Sleeps 4 adults and two children. Bunk bed top for children or pull out of 4 adults. 1 bathroom Kayaking Paddle bikes and boards Fire pit Tour boat next door at Brunelle’s Patio Boathouse restaurant Village commons 1 mile away McCrays farm 1 mile away Ledges golf course 2 miles away Malls etc. 15 min MGM casino 15 min Basketball hall of fame 15 min Airport 45 min Amtrak 10 min Mt sugarloaf 20min. Hiking trails l

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

4.84 out of 5 average rating, 119 reviews

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.

Guest favorite

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, 236 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 (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

Top guest favorite

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

5 out of 5 average rating, 69 reviews

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.

Top guest favorite

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

5 out of 5 average rating, 33 reviews

Charming Riverfront Cottage

We are a 2 bdrm, 1 bath 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 for reading, enjoying the view or doing work. 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)!

Superhost

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

4.85 out of 5 average rating, 79 reviews

Relaxing Home nestled in Rural Hilltown

Beautiful Modern Home with large yard nestled next door to The Berkshires. Enjoy a coffee in the sunroom or deck. There is a large yard, fire pit and kayak access. Alexa enabled in most rooms. A three minute walk to the Blandford Country Store, Breakfast Bistro, and Watson Park. Within 15- 30 minutes of dining, shopping, hiking trails and ski trails. Otis Ridge Ski Area is 15 mins, Tanglewood is 40 mins, Jacobs Pillow 22 mins, Lee Premium Outlets 30 mins, MGM Casino 35 mins.

Top guest favorite

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

5 out of 5 average rating, 13 reviews

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.

Guest favorite

A small rowboat rests on the shore of a calm lake, with two oars placed inside. The scene is framed by lush green grass and dense trees lining the opposite shore, while soft clouds drift above, reflecting the tranquil waters.

Home in Holland

4.93 out of 5 average rating, 107 reviews

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.