Vacation rentals with a kayak in Hampden County

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Popular amenities for Hampden County kayak rentals

House rentals with a kayak

Guest favorite
A vibrant sunset is reflected on the calm surface of the lake, with hues of orange, pink, and purple blending in the sky. Silhouetted trees line the edges, framing the serene waterway and scenic backdrop of rolling hills.
Home in Holland
4.79 out of 5 average rating, 48 reviews

Cozy two bedroom cottage with lake access

DavidRating, 5 stars2 weeks ago
Immaculate and comfortable. Well stocked. Beautiful location. Owner was excellent. Very responsive and friendly. Would without question stay here again. Great base of operations for Brimfield Antique Show.
Guest favorite
Home in Becket
5 out of 5 average rating, 14 reviews

Private Lakehouse in the heart of the Berkshires

AaronRating, 5 stars7 months ago
I want to say thank you to Christopher and his family for allowing my friends and me to stay in their home. it was clean, beautiful, serene and exactly what it was described to be. Christopher, your suggestions on golf courses for my friends and me were exceptional. I hope we were as good of guests as you were hosts!
Top guest favorite
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
5 out of 5 average rating, 32 reviews

Lakefront Retreat at Porcupine Place

JessicaRating, 5 stars2 weeks ago
My family has stayed here multiple times and has loved it. It is a beautifully appointed cottage with a great view and lakefront. It is the perfect place for quiet and relaxation. Carole is awesome to work with.
Guest favorite
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
4.97 out of 5 average rating, 29 reviews

Charming water front cabin with boat dock

johnRating, 5 stars2 weeks ago
If I could give extra stars for how relaxing and peaceful Tatiana's place is I would give it a 10. Ample parking, well appointed and very clean. We attend the Brimfield antique show and this place is a nice to come back to and unwind. We're looking forward to our next stay here.
Guest favorite
The exterior of a black, A-frame house is surrounded by lush greenery. A gravel path leads to the entrance, where a small seating area with blue chairs sits on a deck. Vibrant lilac blooms add a touch of color to the landscape.
Home in Tolland
4.95 out of 5 average rating, 59 reviews

Spacious Home w/ Hot Tub in Private Lake Community

NanditaRating, 5 stars1 week ago
Tina's house was immaculate, comfortable and cozy. We enjoyed the hot tub very much. Kids had a ball in the game room downstairs. Tina responded promptly to our requests. I would highly recommend her home for family get togethers.
Guest favorite
A cozy house is surrounded by vibrant autumn foliage, showcasing a spacious deck that extends toward a flat grassy yard. The clear blue sky provides a bright backdrop, while the trees display rich seasonal colors, enhancing the natural beauty of the setting.
Home in Becket
4.94 out of 5 average rating, 31 reviews

Lakefront Cottage on Private Beach

GillianRating, 5 stars1 week ago
Our family had an AMAZING stay in this cottage. It was clean and comfortable, and just what we were looking for. A quiet spot where we could enjoy fishing, kayaking, biking, etc with the comforts of home. Because of all the amenities offered, we didn’t have to pack too much which is always a bonus! We are already talking about our next visit 😊
Guest favorite
A spacious deck overlooks a tranquil lake, bordered by lush greenery and trees. Several white Adirondack chairs are positioned for relaxation, allowing guests to enjoy the serene water views. The deck's surface is wooden, providing a natural feel to the outdoor space.
Home in Becket
4.92 out of 5 average rating, 25 reviews

Lakefront Jewel By: Evergreen Home

ItayRating, 5 stars4 weeks ago
The house was great and had most of what we needed, we used it as a base for a motorcycle trip.
Guest favorite
The cottage is nestled amidst lush greenery, with a red exterior and black roof. A screened porch is visible, along with an outdoor deck overlooking the lake. A small dock extends into the calm water, reflecting the surrounding trees and garden.
Home in Becket
4.97 out of 5 average rating, 32 reviews

Secluded lakeside charmer

GaryRating, 5 stars4 months ago
We felt right at home in Suzanne's very cozy cabin! The decor is lovely and we were surrounded by beautiful art and antiques. An amazing fireplace and lots of firewood made for lovely evenings by the fire. There are two sliding glass doors overlooking the lake with beautiful natural light and views. The cabin is easily accessible off of established roadways, and getting in and out was a breeze, even in snow. Suzanne and Bob were very easy going hosts and we enjoyed quick and responsive communication. We had all the comforts of home in the kitchen and were able to make most of our meals right at home without a hitch. Beautiful, quiet, woodsy area within thirty minutes of most major towns, like Stockbridge, Great Barrington, and Lenox. I highly recommend Suzanne's cozy cabin and would certainly come again.

Cottage rentals with a kayak

An all-season porch is showcased with large windows providing views of the surrounding trees and lake. A comfortable rocking chair is positioned in the corner, enhancing the serene environment. The light-colored wood flooring complements the bright and airy space.
Cottage in Suffield
4.86 out of 5 average rating, 42 reviews

The Congamond Cottages: Private Lakefront Cottage

KristenRating, 5 stars8 months ago
What a peaceful home away from home! Living the "lake life" for a week was relaxing, beautiful, and fun to explore the lake on foot or the water! It was perfect for what we were looking for!
Top guest favorite
A bright and airy living space features large windows offering views of the serene lake. A dining table with six chairs and a cozy seating area with a navy sofa enhance the room. Natural light floods in through the windows, highlighting the warm wood accents.
Cottage in Wales
4.97 out of 5 average rating, 59 reviews

Sunset and Sunrise views at this lake cottage.

DianeRating, 5 stars2 weeks ago
Oh my gosh! We wish we'd been able to stay another couple of days! This place and location are incredible. Beautiful cottage on a beautiful lake with a fire pit and kayaks available for guest use. Absolutely stunning!
Guest favorite
A view of the rustic cottage situated near the lake, framed by tall trees. Outdoor stairs lead down from the property, showcasing a simple wooden pathway towards the water's edge. Windows with dark shutters reflect the peaceful surroundings.
Cottage in Becket
4.81 out of 5 average rating, 53 reviews

Cozy Cottage on the Lake

PaigeRating, 5 stars5 months ago
The cottage was easy to check into, clean, and very cozy. It was decorated for the holidays which was perfect for our weekend. We enjoyed the fireplace and the games in the cabin as well! I would consider coming back in the summer to enjoy the outdoor area and lake. Ann-Marie and Carl provided really helpful instructions on how to get to the house.
Guest favorite
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
4.95 out of 5 average rating, 83 reviews

Cozy Lakefront Cottage

JohnRating, 5 stars7 months ago
Lovely rustic cottage on a picture perfect lake. Dawn was a wonderful host and made sure we had everything we needed to enjoy our stay. Will stay again!
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, 52 reviews

Berkshire lakefront cabin with modern luxuries

ChristinaRating, 5 stars2 weeks ago
We had the pleasure of staying at Matts place for a weekend getaway that included 6 women. Matt was such an amazing host from start to finish. Beautiful home with gorgeous landscaping on the lake and is set up with everything you could possibly need. The home was immaculate inside and out and was truly even better in person than the already beautiful photos provided. We intend on making this our yearly destination spot! We can't thank you enough for being a super host !
Top guest favorite
Cottage in Otis
5 out of 5 average rating, 17 reviews

Lake Escape: Lakefront Cottage in the Berkshires

JeanneRating, 5 stars7 months ago
My husband and I had a wonderful stay. The cottage was clean and comfortable. The hosts thought of everything and made us feel right at home. We could not have been more pleased and would highly recommend this property.
Superhost
The exterior of an A-frame cottage features a sloped roof, with a welcoming entrance framed by large windows and shutters. A small deck area showcases two green chairs and a patterned mat, surrounded by natural landscaping and pathways leading to the property.
Cottage in Holland
New place to stay

Hamilton Cottage | Cozy Lakefront A-Frame

SteveRating, 5 stars6 days ago
We stayed here with some friends for Memorial Day weekend and can’t recommend the place enough! The area was beautiful, the lake was incredible, and the peace was unbeatable. Would absolutely stay here again!

Cabin rentals with a kayak

The image captures a lakeside view featuring two Adirondack chairs positioned on the grassy shore. A small dock can be seen with a blue boat tied up, and an American flag gently flutters in the breeze against a backdrop of wooded hills.
Cabin in Westhampton
4.89 out of 5 average rating, 9 reviews

Lakefront Westhampton Cabin w/ Beach + Kayaks!

MichaelRating, 5 stars7 months ago
This house on N Shore Rd in Westhampton is a beautiful refuge in the woods of fairly new post and beam construction - at least that's what I think it's called. The house sits on a small lake/large pond and has a small private sand beach, and on offer were a kayak, rowboat, paddleboat and more. Unfortunately the water level was quite low while we were there due to some ongoing work on the dam - the lake is manmade - but we were warned of that in advance and so have nothing to complain about. We stayed for a week and had a wonderful time. A couple of things to note though - it's really dark at night so be prepared to use your phone flashlight to navigate your way from your car to the house. Also, I was surprised to see curtains on only two or three of the windows, so sleeping-in past sunrise is a little difficult if that's your thing. And lastly, the locks on the back doors were not working while we were there, but it didn't bother us enough to let the hosts know. Overall, very nice!
Superhost
A wooden dock extends into a calm lake, featuring two red Adirondack chairs facing the water. A large float is positioned nearby, with trees lining the opposite shore under a partly cloudy sky.
Cabin in Otis
4.87 out of 5 average rating, 54 reviews

Enjoy 43 Acres on Two Ponds!

PatrickRating, 5 stars2 weeks ago
We had a great stay for my daughter’s college graduation. Really enjoyed the house and fire pit. Thanks!
A two-story cabin is set amidst lush greenery, showcasing a spacious deck with seating and a hot tub nearby. A fire pit can be seen in the backyard, surrounded by a well-maintained lawn. The landscape features trees and a gravel path leading to a garage.
Cabin in Tolland
4.56 out of 5 average rating, 27 reviews

Tolland Cabin w/ Private Hot Tub & Grill!

NickiRating, 5 stars3 months ago
Definitely an amazing place, beautiful! But secluded make sure to stock up on groceries and essentials before arriving nearest market is about 16 minutes away. Overall great stay!
Guest favorite
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

DiegoRating, 5 stars4 weeks ago
The place was great. Very private and the deck is a lovely and spacious. The living room is huge, beautiful, and great for a big group to hang out in. Things were clean and it had everything we needed.

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