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Holiday rentals with a kayak in Western Massachusetts

Find and book unique kayak rentals on Airbnb

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Popular amenities for Western Massachusetts kayak rentals

Holiday House Rentals with a Kayak

Top Guest favourite
Home in Valatie
5 out of 5 average rating, 116 reviews

Escape to Lakefront Leisure—Amazing views!

BryanRating, 5 stars3 weeks ago
We had the BEST TIME at this fantastic Lakeside house in Valatie!  The house itself has 3 good bedrooms – 2 large bedrooms upstairs with a nice bathroom and tub.  The downstairs has the other cute bedroom, another full bathroom,  a good sized kitchen open to a great and large living and dining area. The VIEW from the main room is stunning and was our ‘TV’ for the week.  The lake is just gorgeous!  It has a little dock with kayaks and plenty of nice seating and lounge chairs.  It’s great to have a full grass lawn !  The pups loved the house and the yard and the lake!  The house was super clean and roomy but cozy in it’s feel.  So many great little towns nearby – it was just the perfect house to get away from the city!  The community was chill, even tho it was Memorial Day weekend.  Thanks to Michael who was super responsive (not that we needed anything!) but if we had a question. Etc.  Thank you Michael ! We hope to be back for another visit !!!  
Top Guest favourite
Home in Belchertown
4.99 out of 5 average rating, 74 reviews

Moonstone Lake House – romantic, serene, fun!

SarahRating, 5 stars2 days ago
Mighty was a wonderful host, and the sweet cottage on the lake was just peaceful and fun. Every inch of the house has been decorated with care, and the feeling of waking up to look out over the lake is unbeatable. We enjoyed our time so much, and took home lavender sachets generously offered as a reminder of the experience. Highly recommend if you're looking for a beautiful, peaceful place to be in Western MA, with great proximity to the attractions of Amherst and Northampton. Don't miss the Montague Bookmill for used books and a cafe overlooking a rushing river--a treasure!
Top Guest favourite
Home in Hillsdale
5 out of 5 average rating, 53 reviews

Cambridge Hill Farmhouse - Sauna - Swimming Pond

BekahRating, 5 stars2 days ago
This was such a lovely country escape for us tired city kids. The pond was a beautiful backdrop for reading and drawing. We brought our binoculars and walked across to Dan B road, spotting gorgeous birds multiple times a day. Our host, Danielle, was extremely responsive and friendly. A fuse blew our second night there, and Danielle had an electrician out to fix it the next day so we could sleep with AC that night. One warning: if you're tall, there are some very low ceilings and doorways. My partner is 6'2 and hit his head repeatedly on the bathrooms' vaulted ceilings and the kitchen doorway. The house would be great for a big group, or a family with kids -- the playroom is delightful and the big, fun kitchen makes you want to fill with your friends and eat and talk for hours. We're very grateful for our quiet getaway there!
Guest favourite
Home in Copake
4.96 out of 5 average rating, 196 reviews

Lakefront +pets +skiing +bbq +firepit +games

AddisonRating, 5 stars2 days ago
We had an incredible stay at Frank’s place. Rarely do airbnbs exceed our expectations, and this one blew ours away. It was so much nicer than the photos. The lake view, the renovations, everything. We will 100% be back
Top Guest favourite
Home in Becket
5 out of 5 average rating, 33 reviews

Berkshires Lakefront Stylish Retreat w/Gameroom

BenRating, 5 stars4 weeks ago
What an amazing stay. The house is right on a peaceful pond and our kids had the best time exploring every day by canoe. We saw foxes, beavers, tons of birds, and ended each day with s’mores by the fire. Total magic! The house itself was super comfortable and had everything we needed. And the full-size arcade machines were a huge hit with the kids! We’d come back in a heartbeat!
Guest favourite
Home in Westminster
4.89 out of 5 average rating, 188 reviews

Lakefront, view of ski mtn, fireplace, sauna

BenRating, 5 stars1 month ago
This spot was excellent for my group. There were plenty of comfortable sleeping options for everyone and the space was even more spacious than expected. We also enjoyed the views and peaceful surroundings of the pond. Tyler was able to accommodate a late checkout as well, which was greatly appreciated.
Top Guest favourite
Home in Washington
5 out of 5 average rating, 105 reviews

Newer Home on quiet 200 acre lake - sleeps 6

NoraRating, 5 stars2 days ago
We had such a wonderful time in New Hampshire thanks to Melora! The house was exactly what we were looking for. The views of the lake were to die for!
Guest favourite
Home in Orange
4.96 out of 5 average rating, 79 reviews

Four Season Cozy Cottage on Lake Mattawa

CricketRating, 5 stars1 month ago
We had a fantastic long weekend on Lake Mattawa. Came to celebrate our son’s graduation from UMass. It was an easy 30 minute drive to campus for graduation. The cottage was a perfect place to hang out as a family…we paddled, fished, played games and cooked. Enjoyed eating on the deck and loved having our morning coffee on the sun porch. Really liked the Quabbin Harvest Coop (awesome local produce and supplies) and had an amazing sandwich at the Corner Cafe. Hope to return!

Cottages with a kayak

Top Guest favourite
Cottage in Valatie
4.99 out of 5 average rating, 143 reviews

Kinderhook Lakefront Retreat-private, kayaks, ac

DuncanRating, 5 stars2 weeks ago
Amazing place. Lisa & Steve's cottage made for an amazing weekend. We had pretty bad weather but it was still a great weekend. The lake is so peaceful and the set up of the cottage is perfect. The cottage has everything you need, as well as everything you didnt know you needed! We'll definitely be back. Ate at The Aviary, The Smokehouse & The Maker (Hudson) - all very different but incredible.
Guest favourite
Cottage in Poughkeepsie
4.91 out of 5 average rating, 356 reviews

Be in Nature at this Gorgeous Riverfront Cabin

AaryaRating, 5 stars1 week ago
We loved the place, it was a beautiful home with lots of light and accessible green space. It was perfect for a short getaway. It’s a short drive from nearby towns and was very easy to find based on the directions. Mark was a responsive and accommodating host and we had a wonderful time in his airbnb.
Top Guest favourite
Cottage in Munsonville
4.89 out of 5 average rating, 219 reviews

Camp -Granite Lake, Munsonville, NH

BrittanyRating, 5 stars5 months ago
We came up to Joan's lovely cottage for a peaceful, hiking Christmas vaca and it was absolutely perfect. Joan was a wonderful host, very friendly and generous. We wish Joan was our granny too! Granny camp was comfy, cozy, on a beautiful lake, with lots to do in surroundings areas. Would love to come back in the summer! Thank you!
Top Guest favourite
Cottage in Colchester
4.97 out of 5 average rating, 176 reviews

Lakefront peaceful getaway cottage

AudraRating, 5 stars1 week ago
We loved staying at this lakehouse! Our kids loved the bunk beds and we had everything we needed to make full breakfasts and dinners. The kitchen and bathrooms were fully stocked and clean. The neighborhood is very peaceful and if you need anything, Westchester Market is only 5 minutes away. If you visit the market and run into Kurly (you'll know him when you see him), you'll get lots of local recommendations and an entertaining conversation. Doreen is a wonderful host and gave us lots of recommendations for local restaurants, all of which were great. We stayed here for a week and highly recommend this cottage.
Top Guest favourite
Cottage in Weare
4.94 out of 5 average rating, 286 reviews

Seasonal lake side cottage

LorraineRating, 5 stars2 weeks ago
Really incredible cabin! It’s cute - homey and private! Such cute touches! Sadly it rained and we didn’t get to enjoy the water , but it still had a cute indoor space overlooking the water, great tunes and played games they had! It was a great get away! Don’t cancel because of rain.. it was delightful! Great local eatery too !! Highly recommend Stark Tavern.. Very friendly area! Will be back we enjoyed our time! Thank you for hosting!
Guest favourite
Cottage in Newbury
4.95 out of 5 average rating, 222 reviews

Large Private Lake House

JulieRating, 5 stars1 week ago
What a beautiful peaceful oasis! The loons with their haunting calls at night were a highlight. A bald eagle sighting while out in the kayak was magnificent. The fenced in yard for our dog was such a great feature. An wonderfuly relaxing trip.
Guest favourite
Cottage in Lanesborough
4.84 out of 5 average rating, 279 reviews

Wildlife Lakeside Cottage; views/wildlife

SonyaRating, 5 stars1 month ago
This is a beautiful and peaceful cottage with easy access to shops and restaurants in the area. It was perfect for a sisters weekend. Highly recommend.
Top Guest favourite
Cottage in Thompson
4.99 out of 5 average rating, 142 reviews

Waterfront Cottage in Thompson CT • Dogs Welcome

HeatherRating, 5 stars6 days ago
Jane really is a Super host of the cutest cottage ever!! Not only has the cottage exactly as described, it was super clean!! We have never been really comfortable staying at an Airbnb until now!! This cottage and Jane really made our stay one of the best visits to this area we have ever had! We can not recommend this cottage enough! We miss it already and are looking forward to our visit!!

Cabin rentals with a kayak

Guest favourite
Cabin in Andover
4.95 out of 5 average rating, 117 reviews

Little House on the Lake in the Forest

BrentRating, 5 stars2 weeks ago
Wonderfully peaceful, tranquil setting on the lake, in the woods. Perfect for a quiet getaway to reflect and renew. Everything was exactly as described, and Laurel was a gracious and responsive host. The cabin was rustic yet newly refinished, very clean, well equipped. Enjoyed the screened in gazebo, loved sitting by the water as well, plus experiencing the lake in the canoe and kayak. Also enjoyed some great hiking and views at Mt Kearsarge which is less than 20 minutes away. And finally -- the sounds of the loons after sunset. Grateful for three days of renewal!
Guest favourite
Cabin in Stoddard
4.83 out of 5 average rating, 131 reviews

Cozy Cabin with Lake Access

PaulRating, 5 stars8 months ago
We had a great time at Molly's cabin. We were looking for a quiet stay and we had that. Lots of walking and hiking. The cabin was just as described snd Molly was a fantastic host. Thank you Molly!
Top Guest favourite
Cabin in Kingston
5 out of 5 average rating, 214 reviews

Lakeside Cottage: Boulder's Bluff

HaileyRating, 5 stars2 days ago
My partner and I couldn’t have enjoyed our stay more. The cabin is tucked away, but Edward’s clear instructions made getting there a breeze. It was spotless, thoughtfully stocked, and we felt genuinely cared for. The lake water was crystal clear, with wildlife all around. We took full advantage of the kayaks, rowboat, floats, and fishing gear, and ended each evening watching the sunset from the dock. The neighboring cabin was occupied by Edward’s family, but they were kind, helpful, and never intrusive—actually, their presence added a sense of comfort in such a secluded spot. It was the perfect weekend escape. We hope to be back soon! Thank you, Edward!
Top Guest favourite
Cabin in Comstock
4.97 out of 5 average rating, 110 reviews

East Cabin

AmyRating, 5 stars2 weeks ago
We had a wonderful stay. We weren't at the cabin much during the day as we were out and about, but when we were there it was peaceful and great. We loved visits from the very friendly dogs. We also had some fun walking around the ponds and kayaking in them. The instructions to arrive at the cabin we very clearance easy to find. I would recommend this cabin!
Top Guest favourite
Cabin in Catskill
4.91 out of 5 average rating, 236 reviews

Modern secluded Log Cabin in woods-great location!

AlstonRating, 5 stars2 months ago
This is the perfect cabin retreat. Beautiful property with incredible back porch views, stunning fireplace, creekside access, and gobbling turkeys in the distance. It was just what I was looking for to celebrate a birthday with friends. Secluded enough to feel private but close enough to a charming town for drinks and coffee. Jim was also super communicative and made it easy to settle in—he even gave me a heads up about the weather that weekend to make sure we were packed appropriately. I was considering a couple of places, and I’m so happy I chose this one. Highly recommend a visit. P.S. The heated floors are a really nice touch.
Top Guest favourite
Cabin in South Sutton
4.99 out of 5 average rating, 273 reviews

Swim & Fish Pond| River| Fire Pit |Close to Skiing

KimRating, 5 stars4 days ago
This was absolutely the best place we have ever stayed at. Dominic was so nice. The home was perfect. We were there for the Laconia bike rally. We loved being out in the quiet. We had friends with us who loved it also. I would love to bring my immediate family back here but we have 10 grandchildren and with boys and wives we have too many to stay there😩. But I would recommend this home over and over again👏🏻 Kim P.
Guest favourite
Cabin in Stoddard
4.81 out of 5 average rating, 245 reviews

Waterfront Cabin on Beautiful Highland Lake!

KarenRating, 5 stars5 days ago
This is our 3rd year staying here at the end of June. Sure June can be rainy, but it does not even matter at this place. You are right on the water, so even in the rain, you can jump in the water, kayak in the rain, or just rock in a rocking chair by the screen door and listen to pitter patter on roof and in lake. The loons were very active too with the cool days and nights. We love the peace and quiet of early season when not too many boaters. We fired up the wood stove on cold mornings and felt like we were real homesteaders in our rural cabin! It is just down the lane from the main house, but feels very private. Love it!!
Guest favourite
Cabin in Coventry
4.86 out of 5 average rating, 174 reviews

Lake - PetsOK - Wi-Fi- W&D - Fire Pit - Kayaks

NikodemRating, 5 stars5 days ago
My friends and I had a wonderful time, it is a very cosy house/ property. Joe was very friendly and clear about instructions making it an easy stay!

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