Holiday rentals with a kayak in The Berkshires

Find and book unique kayak rentals on Airbnb

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Popular amenities for kayak rentals in The Berkshires

House rentals with a kayak

Top guest favourite
Home in Canaan
4.96 out of 5 average rating, 54 reviews

Private Retreat: Hot Tub! Movie Room! Pool Table!

MusserRating, 5 stars1 week ago
This was a bit of a last minute decision to come to the Berkshires and I was grateful that Tiffany could accommodate some quick changes. The house is just as described--lots of space, nice setting, pool table was fun (and cool in the basement), and I appreciated that our two dogs could be included. Even though the house is in NY, it is not far from the hiking trails and museums. We would like to come back--a lot more to see and do in this area.
Guest favourite
Home in Ancram
4.99 out of 5 average rating, 181 reviews

Everything on one floor 2 Bdrm/1.5 Bth & Pets Ok

AdelyaRating, 5 stars1 month ago
The best Airbnb we’ve ever stayed at! It truly felt like home—every detail was so thoughtfully taken care of. You have everything you need for a comfortable stay, from a well-stocked space to those little touches that make a big difference. The bed and pillows were super comfortable, and even though it rained, the hosts had dry firewood ready for the fireplace, which made it feel extra warm and inviting. We loved sitting by the lake and even saw a fish jump out of the water—such a magical moment! Communication with the host was excellent from start to finish. And thank you so much for approving our cats to stay with us—it meant the world. If we could give 10 stars, we absolutely would. Highly recommend this place to anyone looking for a peaceful and welcoming getaway. Thank you for an unforgettable stay!
Top guest favourite
Home in Valatie
5 out of 5 average rating, 115 reviews

Escape to Lakefront Leisure—Amazing views!

BryanRating, 5 stars2 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 !!!  
Superhost
Home in Monterey
4.82 out of 5 average rating, 79 reviews

Rustic 3bd Lake Front Country Cottage

EdwardRating, 5 stars1 month ago
Peaceful, perfect getaway. Jaryn’s cabin on Lake Garfield was the ideal escape—cozy, quiet, and surrounded by nature. We loved the lake access, morning coffee on the porch, and how easy everything was.
Guest favourite
Home in Coventry
4.98 out of 5 average rating, 113 reviews

Cozy cottage 5 minutes from UConn

JdRating, 5 stars4 days ago
Immaculate space. Location and views are incredible. Check in was easy, hosts were very communicative and you can tell they put a great deal of energy into their home. They also included fresh eggs from their farm. We were obsessed with it and will definitely rebook.
Guest favourite
Home in Egremont
4.91 out of 5 average rating, 82 reviews

Modern and Stylish Country Lakeside Cottage

NikiRating, 5 stars3 weeks ago
This was my second time staying at Maureen’s beautiful lakeside home and it surely won’t be my last. It’s the coziest, peaceful and inspiring place. Looking forward to future visits!
Guest favourite
Home in Pine Plains
4.98 out of 5 average rating, 123 reviews

Twin Island Lake House • Hot Tub

KaiRating, 5 stars3 weeks ago
We had a wonderful stay at this location during my daughter’s graduation from Bard College. The location has beautiful views of the lake and the layout of the property was perfect for the family to gather and celebrate, while also giving everyone the space for their own quiet time or rest. I would definitely recommend this location and hope to have the opportunity to stay again.
Guest favourite
Home in Valatie
4.97 out of 5 average rating, 32 reviews

Majestic lake front house

PeterRating, 5 stars1 month ago
We had a great time at Francois & Ann's oasis by the lake. It was so relaxing to wake up, look at the lake, and listen to birds chirp. If you are looking for isolation, this place does the trick, We didn't see anyone all week on the lake or at the other cabins until the day we left. The lake has excellent fishing. With little effort, we caught several decent-sized bass and pickerel right off the dock. The location is ideal. You feel like you are out in the country, but are close to great restaurants in Kinderhook and only 25 minutes from Hudson or Albany. It's also only an hour from Mass Moca and 90 minutes to Cooperstown. Francois and Ann were very communicative and quickly responded to questions and comments.

Cottage rentals with a kayak

Guest favourite
Cottage in Putnam Valley
4.96 out of 5 average rating, 165 reviews

Private Lake House 1 Hour to NYC & Near Westpoint

LoriRating, 5 stars1 week ago
WOW! Could not have been a more perfect stay! The setting was so beautiful, serene and peaceful. We had lot's of activity paddle boarding, kayaking, BBQing! Most of the time we were the only people on the lake. Early June was a perfect time to be there. It was just such a gorgeous and relaxing setting. The house was fabulous for our family reunion and ideal for our adventurous 1 year old. Our host was simply amazing. He had items delivered to our door when we had questions...even sent us a bag of groceries to make Smores on the lake! We hope to make this an annual event! We'll definitely be back.
Top guest favourite
Cottage in Whitehall
4.99 out of 5 average rating, 207 reviews

Hillside Cottage @ The Mettawee Retreat

HeatherRating, 5 stars6 days ago
Our stay was fantastic! The cabin was clean, comfortable and cozy. There was obvious attention paid to the little details that make a trip extra relaxing. I don't think that there was anything that we wanted that wasn't thought of and ready for us. We booked our stay with the intention of disconnecting and unwinding& we were able to do exactly that. The property is absolutely magical! There was an endless amount of beautiful flowers and wildlife with a winding river. Our favorite part was relaxing on the deck watching the deer and birds. The customer service couldn't have been better. They went out of their way to be helpful and friendly. we definitely recommend & plan to return for a longer stay!
Top guest favourite
Cottage in Valatie
4.99 out of 5 average rating, 142 reviews

Kinderhook Lakefront Retreat-private, kayaks, ac

DuncanRating, 5 stars1 week 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 Orange
4.91 out of 5 average rating, 185 reviews

The Lake Cottage: A Sweetwater Stay

CourtneeRating, 5 stars1 month ago
Excellent and beautiful location. Very scenic and tranquil. The location allows you to relax while still being in reach of everything. The unit was very well maintained and clean. All the Amenities of home without the chaos.
Guest favourite
Cottage in Poughkeepsie
4.91 out of 5 average rating, 354 reviews

Be in Nature at this Gorgeous Riverfront Cabin

MJRating, 5 stars5 days ago
A lovely home with beautiful views of the surrounding woods from each room. Very clean, modern, and comfortable with a well stocked kitchen. Mark provided detailed and useful info on the place and the surrounding area. A great spot if you’re looking for some peace and quiet close to all the local attractions of the Hudson Valley.
Top guest favourite
Cottage in Gloversville
4.93 out of 5 average rating, 124 reviews

Peaceful "Sleepy Loon Cottage" on Lake Edward ADK

KellyRating, 5 stars3 days ago
Lori’s place was everything listed ,and more !!!! We enjoyed the peace and quiet of the surroundings, the cabin was adorable, and access to the boat ,and kayaks was awesome!!! My husband and daughter enjoyed the fishing , and my son enjoyed his daily walks. I personally enjoyed sitting on dock , or the screened in porch enjoying a good book!!!! My family had a great at Lori’s place!!! Thank you, Kelly
Top guest favourite
Cottage in Colchester
4.97 out of 5 average rating, 175 reviews

Lakefront peaceful getaway cottage

AudraRating, 5 stars3 days 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.
Guest favourite
Cottage in Putnam Valley
4.89 out of 5 average rating, 272 reviews

Lakefront Cottage near Hudson Valley

ZoeRating, 5 stars2 weeks ago
My husband and I had a wonderful weekend trip at Tony’s lakeside cabin to celebrate our anniversary. The setting was idyllic, and the cabin was cozy and comfortable. We loved waking up to the beautiful view of the lake! Tony was a friendly and helpful host, and the whole weekend went very smoothly, from check in to check out. We would definitely come back!

Cabin rentals with a kayak

Superhost
Cabin in Jefferson
4.89 out of 5 average rating, 154 reviews

Dino's Black Bear Cabin

JustinRating, 5 stars1 month ago
Lovely and peaceful cabin for a weekend out of the city. Really enjoyed the downstairs space and amenities like the hot tub and grill. We appreciated the hosts' responsiveness - they were glad to assist us with returning a forgotten item!
Guest favourite
Cabin in Hoffmeister
4.85 out of 5 average rating, 108 reviews

Cabin on the Creek - cozy & private

LouiseRating, 5 stars1 month ago
We had a great stay fishing, walking and just relaxing. Did some driving to Speculator and Indian Lake too. Good plan when it’s buggy!
Guest favourite
Cabin in Huguenot
4.94 out of 5 average rating, 269 reviews

Tranquil Lakefront Cabin!

CaleRating, 5 stars3 weeks ago
Very nice house, good fishing and wildlife nearby. A little closer to the neighbors than expected, but overall a great place and would love to come back
Guest favourite
Cabin in Stamford
4.95 out of 5 average rating, 138 reviews

ROMANTIC LAKE-FRONT Rustic Cabin by NYC Designer

PhilRating, 5 stars1 month ago
Ivan's home was beautiful. The location on the lake was so quiet and peaceful. It was clean and it had everything we needed. We look forward to coming back again!
Guest favourite
Cabin in Coventry
4.88 out of 5 average rating, 136 reviews

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

MariaRating, 5 stars1 week ago
Joe's Cabin was exactly as described in the listing. Beautiful, peaceful neighborhood, and right next to the lake. Our family came into town for an event and the cabin was the perfect place to relax and unwind. Every part of the home was clean, beds were very comfortable, and every amenity was available if needed. Host was very responsive and communicated well. We will definitely be back.
Guest favourite
Cabin in Athens
4.94 out of 5 average rating, 103 reviews

Charming Lakefront Cabin with Hot Tub

ModouRating, 5 stars2 days ago
We had a great time here with our 9 month old baby. The pictures don’t do the house justice. Access to the lake for swimming and kayaking and the facilities (pools, beach, basket ball and tennis court) make this a great place for an active vacation. The house has everything you need to travel with a young child (toys, changing table, pack ‘n play and even black out shades). The towns of Athens and Coxsackie are a few minutes away and have decent food and drink options. We would love to come back!
Top guest favourite
Cabin in Kingston
5 out of 5 average rating, 212 reviews

Lakeside Cottage: Boulder's Bluff

AlexRating, 5 stars7 months ago
We loved our stay at Ed's cabin. it is a real gem and perfect for a long weekend away. we loved the fireplace, the rocking chairs, the windows with views out onto the lake that make you feel like you're right over the lake and in the trees. there were nice restaurants and hikes in the area, but we were perfectly content watching the lake and reading from the cabin. Ed was perfectly accommodating and extremely generous with his space, couldn't recommend more highly.
Top guest favourite
Cabin in Comstock
4.97 out of 5 average rating, 110 reviews

East Cabin

AmyRating, 5 stars1 week 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!

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