
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

Private room in Worthington
4.97 out of 5 average rating, 120 reviewsCountry Luxury in the Heart of the Berkshires
RyanRating, 5 stars11 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 stars1 month 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 stars9 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 stars7 months ago
Easy check in and check out. Very responsive host with any questions and concerns.
Top guest favourite

Home in Becket
5 out of 5 average rating, 32 reviewsBerkshires Lakefront Stylish Retreat w/Gameroom
LaurenRating, 5 stars3 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 stars6 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, 44 reviewsRiver View Bedroom in 1850s Grist Mill
DanuteRating, 5 stars1 week ago
We had a nice stay. Our dog Django fit right in as well and Gregory approached him w kindness. River sounds were nice and the place as unique and way to find. We took a hike the Gregory recommended and it did not disappoint. Beautiful area. We had a nice time at the locals coop w the manager and her friend as well. Nice stay. Beautiful area.

Home in Plainfield
4.73 out of 5 average rating, 156 reviewsSpring spectacular w fireplace, WiFi, BBQ & forest
MariosRating, 5 stars2 months ago
We had a fantastic stay at this Airbnb! The place was cozy, well-equipped, and perfect for our group. The kids loved the games and toys, and the fireplace made for a great place to relax after skiing. The location, just 15 minutes from Berkshire East, was ideal. That said, winter travelers should be prepared for challenging road conditions. It snowed heavily during our stay, and while private plowing services arrived, it was usually around 11 a.m. If it snows overnight, expect to shovel the large driveway to get the cars out early in the morning. The roads are steep and not always well-plowed, so a four-wheel-drive vehicle, winter tires, or chains are highly recommended. On our last morning, a tree fell out front, blocking the road and knocking out power. These things happen, and it wasn’t the host’s fault, but the remote location means services may be limited. Despite that, we had a wonderful time!
Cabin rentals with a kayak
Superhost

Cabin in Otis
5 out of 5 average rating, 4 reviewsBerkshires Lakefront Boho Modern Retreat
MelissaRating, 5 stars2 months 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
4.97 out of 5 average rating, 69 reviewsPanoramic Sunroom | Soaking Tub | Modern Cabin
KevinRating, 5 stars5 days ago
Can’t say enough good things here. The location is amazing, the home is beautifully decorated. The sunsets are perfect. The hosts are there if you need anything and not if you prefer. Incredible value for the experience. We will be back !

Cabin in Westhampton
5 out of 5 average rating, 8 reviewsLakefront Westhampton Cabin w/ Beach + Kayaks!
MichaelRating, 5 stars6 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, 37 reviewsHappy Valley Lake House Waterfront • Kayaks/Canoe
Erika & PatrickRating, 5 stars3 days ago
Easy check in, clean, pleasant cabin. Enjoyed watching the turtles at the pond. Woodstove was good on a chilly night for the living room as the minisplit heat kind of hovers higher above in the loft. Very quiet because off a dirt private road & neighbors didn’t seem to be around (off season weekday stay). House had just enough of all I needed in kitchen. Appreciated the notes the host had left on house procedures, & hiking etc nearby.
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- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Monadnock State Park
- Six Flags New England
- Berkshire East Mountain Resort
- TPC River Highlands
- Taconic State Park
- Bushnell Park
- Mount Snow Ski Resort
- Mohawk Mountain Ski Area
- Mount Greylock Ski Club
- Mount Sugarloaf State Reservation
- Norman Rockwell Museum
- Bash Bish Falls State Park
- Hartford Golf Club
- Bousquet Mountain Ski Area
- Naumkeag
- Beartown State Forest
- Otis Ridge
- Rockledge Golf Club
- WIckham Park
- Bright Nights at Forest Park
- Talcott Mountain State Park
- Bigelow Hollow State Park