
Holiday rentals with a kayak in Hampshire County
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Hampshire County
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.
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House rentals with a kayak
Top guest favourite

Private room in Worthington
5 out of 5 average rating, 119 reviewsCountry Luxury in the Heart of the Berkshires
RyanRating, 5 stars10 months ago
Jim and Michelle were such welcoming and accommodating hosts. Their home is the perfect location tucked away in the countryside. Enjoying coffee and breakfast with Michelle on Sunday and their super friendly dog, Darby, was such a pleasant treat. Would love to come back more and explore the area. One thing to note, if you have Verizon you'll be off the grid here because cell service is sparse - but that's probably the best way to fully immerse yourself in the property and truly enjoy it!
Superhost

Private room in Leverett
4.78 out of 5 average rating, 36 reviewsCozy bedroom in 1850's Grist Mill
EnzoRating, 5 stars2 weeks ago
I had a plan to attend a concert nearby but wound up staying at the house the whole time. I needed a rest and the house was calm, quiet, and next to a dramatic river. Gregory was a little slow to warm up before my visit but he turned out to be a very warm, gracious, and generous host. We enjoyed a conversation by the fire and he invited me to share food, and put on music by the artist whose concert I missed do that I could still enjoy it! I slept really well and left feeling that while it I hadn’t done very much, it had been a very restorative place to seclude myself.

Home in Becket
5 out of 5 average rating, 22 reviews"The Robin's Nest" Lakefront home Robin Hood Lake
LoriRating, 5 stars8 months ago
Working with Tom and Amy was so easy. They were wonderful hosts. The setting was idyllic and all amenities were provided. The fenced in yard was great for our dog. We all had a relaxing, restful vacation with lots of floating and kayaking. The area had lots of fun things to do nearby. We would return every summer if possible.

Home in Becket
4.5 out of 5 average rating, 4 reviewsBecket Home w/ 3-Season Porch: Walk to Lake Access
ConnorRating, 5 stars6 months ago
Easy check in and check out. Very responsive host with any questions and concerns.
Top guest favourite

Home in Goshen
5 out of 5 average rating, 11 reviewsWaterfront Wonderland | Luxe Log Cabin (Sauna/Gym)
ChristopherRating, 5 stars1 month ago
Wow, this home exceeded expectations at every turn. The pictures and reviews do not do it justice. The host was amazing, she ensure a quick and easy check-in and followed up with us to make sure we had everything we needed. Two ski locations near by and the town of Williamsburg just 5 minutes away for all your needs. House had every amenity you could possibly need, and the home was extremely clean. We will be back and recommend to all of our friends. Thank you !!
Top guest favourite

Home in Becket
5 out of 5 average rating, 32 reviewsBerkshires Lakefront Stylish Retreat w/Gameroom
LaurenRating, 5 stars2 months ago
We had a lovely long weekend here with family, enjoying the surrounding areas for winter fun. Christina was so responsive and helpful, the space was cozy and the outdoor areas gorgeous!

Private room in Leverett
4.8 out of 5 average rating, 10 reviewsAiry room with hiking, breakfast
NatalieRating, 5 stars5 months ago
This place is a gem! I was looking for an area in a quiet area and this Airbnb was the perfect little nook to crash in. The bed was SO comfy and the Host was very friendly and responsive! She had a wonderful assortment of teas and fresh eggs that you can cook with. I went kayaking in the lake close to their home and it was so beautiful out there. I would say this is the perfect room for someone looking for a quiet nook in the woods!!
Guest favourite

Private room in Leverett
4.98 out of 5 average rating, 41 reviewsRiver View Bedroom in 1850s Grist Mill
AlyssaRating, 5 stars4 months ago
Gregory is a friendly host who is very welcoming and keeps a beautiful home.
Cabin rentals with a kayak
Superhost

Cabin in Otis
5 out of 5 average rating, 4 reviewsBerkshires Lakefront Boho Modern Retreat
MelissaRating, 5 stars1 month ago
What a beautiful home in a gorgeous setting. We unfortunately got caught in a winter storm during our stay. Christina went above and beyond to make sure we were taken care of during the inclement weather. We will definitely stay here again!
Top guest favourite

Cabin in Athol
5 out of 5 average rating, 59 reviewsPanoramic Sunroom | Soaking Tub | Modern Cabin
RobertRating, 5 stars5 days ago
Great spot on a nice pond. Our stay was pleasant, peaceful and we enjoyed the woodsy location of the home. Amanda was very responsive when we had questions. We definitely recommend this Airbnb.

Cabin in Westhampton
5 out of 5 average rating, 8 reviewsLakefront Westhampton Cabin w/ Beach + Kayaks!
MichaelRating, 5 stars5 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!
Guest favourite

Cabin in Shutesbury
4.97 out of 5 average rating, 35 reviewsHappy Valley Lake House - Waterfront w/ canoe!
JennRating, 5 stars4 months ago
Sam and MaryAnn have created a sweet oasis. The cabin itself is cozy and has tons of natural light and the full-sized frig and oven were perfect for hosting Thanksgiving. We especially loved the loft, the window seat, and the wood stove. The drive to the cabin is quintessential New England and the setting is lovely. Most of all, we appreciated the thoughtful communication and help we received from the hosts. Thank you for sharing your place with us.
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- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Berkshire East Mountain Resort
- Six Flags New England
- Taconic State Park
- Monadnock State Park
- Bousquet Mountain Ski Area
- Mount Sugarloaf State Reservation
- Mohawk Mountain Ski Area
- Beartown State Forest
- Mount Snow Ski Resort
- Bash Bish Falls State Park
- Naumkeag
- Butternut Ski Area and Tubing Center
- Pineridge Cross Country Ski Area
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Berkshire Carousel
- Canterbury Farm
- Clarksburg State Park
- Berkshire Botanical Garden
- Otis Ridge
- Hancock Shaker Village
- Rockledge Golf Club