
Vacation rentals with a kayak in Berkshire County
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Top-rated kayak rentals in Berkshire County
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House rentals with a kayak

Waterfront oasis in heart of Berkshires
The location was peaceful and beautiful with great local restaurants, farms, and hiking. The reservoir was a nice amenity with the kayaks and canoe. The house was well maintained and comfortable with pretty views on the first floor. We enjoyed our stay

Little Longbow Lakefront Chalet
Jaclyn’s home is the perfect place to get away and relax. Being on the water with a wood burning fire place was absolutely lovely. The home was clean, well organized, and Jaclyn was always responsive when we had a question. The home was an easy 20min drive to a lot of fun small towns. There was a little traffic noise when we were outside from the highway, but it was peaceful otherwise

Modern and Stylish Country Lakeside Cottage
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!

Summer Family Fun at Hygge House on Richmond Pond
The Hygge House was a lovely spot to spend my birthday weekend with my family and friends. We took advantage of so many close-by activities. But the highlights were at the house itself - paddling the canoe and kayak through the water, outdoor dinner, and s’mores at the fire pit. Jessica was also so easy to communicate with and super accommodating during a personal emergency we experienced. We loved our stay and would love to come back again soon.

Private Lakehouse in the heart of the Berkshires
We had a lovely thanksgiving getaway at Christopher's place. The neighborhood was blanketed in snow turning it into a winter wonderland. The house was cozy, and we especially enjoyed the sun room with its beautiful views. Christopher was very responsive the entire time. Thanks for a great stay!

Lakefront Cottage on Private Beach
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 😊

Lakefront Jewel By: Evergreen Home
This location was amazing. The lake is peaceful and a perfect place to relax. The house is amazing and the hosts thought of every single need we might have. It was a wonderful stay!

Secluded lakeside charmer
We had an absolutely amazing time at Suzanne's beautiful lakehouse. It was super cozy and includes so many amenities that make the stay so comfortable. Suzanne was a great host and available for any questions. We loved their home and hope to stay there again.
Cottage rentals with a kayak

Secluded Country Getaway on 22 acres
An absolute gem of a property, super fun to explore and a multitude of options for relaxing and enjoying the natural scenery and sounds. Location is very convenient, just a couple minutes from some great restaurant options (and grocery store).

Plan your Berkshires by the lake
The cabin is really cute. They have everything you could need there. I really loved the screened in lanai. My husband and I stayed for a long weekend with our dogs. Everyone we ran into was friendly and respectful. It’s the prefect place for a quiet getaway. The lake is so clear and it was so nice to take a dip to escape the hot weather. The lake beach is not pet friendly but there are plenty of places that are. There are several trails that allow dogs and the orchard up the road also allows dogs just to name a few. We really enjoyed our stay. It’s a great area to recharge.

Berkshire Cottage - Relaxation Destination
Jane's cabin was just as described. peaceful location with beautiful views.

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
The cottage is clean and comfortable and the kitchen is well stocked. This is a nice place to serve as home base to explore all that the Berkshires have to offer.

Cozy Cottage on the Lake
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.

Lake Escape: Lakefront Cottage in the Berkshires
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.

Pet friendly Cottage on Lake; Hike, Swim, Kayak
Loved the quick weekend getaway from the city! Wanted somewhere we could stretch out into.. which Ayren’s house fully is.. loved playing the many board games provided and watching movies in the late evenings.. plus a few walks down to the lake and drive to town which is less than 15 min away.. A very communicative host with clear instructions and well laid out amenities and basic kitchen condiments.. Thanks again for a great weekend !

Norte Maison 2 beds 2 Baths Minutes to Jiminy Peak
One of the most clean air bnb I have stayed in. It was spotless and comfortable. The hot tub and kayaks were easy to use and just a few yards walk to the water. I would not change anything about this house. And thank you Darcy for being such a great host!
Cabin rentals with a kayak

Simple, rustic, cozy get away
It was a perfect price. With the ABNB it was double+. I would rather pay John more for the one night personally, than what I did. And have done twice. I have always left the place the same or better than I found it. I understand the cleaning fee, but kills single fathers like me for a 1 night trip. That being said. Walker cabin is great! Kayaks, all safety gear, fully outfitted down to toothpicks, brushes, floss, ect. You think you forgot it. It’s there. Baby monitors!

Glamping in the Berkshires w/ car charging station
Beautiful setting in the woods grandkids loved it. Toys for inside and out. Bows and arrows! Tadpoles, campfire, barbecue equipment. Rained, fortunately umbrellas were available and anything else you could think of for glamping. If it hadn’t rained so much we would have tried out the kayaks. Rustic, comfortable, lush forest beautiful flowers. Lovely setting peaceful.

Berkshires Treehouse Retreat- Lake access!
The place really worked for my family. I went with my brother and his wife and my husband. They had one floor. We had the second floor and the first floor was like a basement. So it’s really great if you have lots of people because there’s a lot of space there. It had everything we needed. We really appreciate it. Thanx Sarah

Cozy Stockbridge Cabin - Walk to Beach & Lake!
Peaceful quiet private New England home with thoughtful updates. The Fall chill went quickly on arrival and the rest of. the was cozy warm. Great wifi.

Wildlife Retreat in the Forest
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.

Enjoy 43 Acres on Two Ponds!
We had a great stay for my daughter’s college graduation. Really enjoyed the house and fire pit. Thanks!

Beautiful Lake Front Cabin
Mary’s place is truly magical. It’s the perfect spot for a family to enjoy the lake and each other. Most of all, Mary and her family are exceptional people, and we enjoyed getting to know them and felt very lucky to be in their special spot. We cannot recommend this place enough!

Berkshires Lakefront Boho Modern Retreat
Staying at this lake house was peaceful and lovely -- the house is updated, so clean, right on the pond and great for a family. Christina is such a responsive host. We can't wait to come back!
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- Six Flags New England
- John Boyd Thacher State Park
- Albany Center Gallery
- Bushnell Park
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Zoom Flume
- Kent Falls State Park
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Beartown State Forest
- Bright Nights at Forest Park
- Hartford Golf Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Opus 40
- Naumkeag
- Brignole Vineyards
- Bousquet Mountain Ski Area