
Holiday rentals with a kayak in Berkshire County
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Top-rated rentals with kayak 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!

New Shaw Pond Skytop Retreat in the Berkshires
We stayed here on our way to Stowe to break up our long drive with an 8 and 2 year old. It ended up being a wonderful mini trip that we didn't want to leave. The house exceeded our expectations in terms of quality, cleanliness, and amenities. And the location was excellent - about 10 to 12 min to the nearest grocery store and downtown with restaurants, Edith Wharton's estate about 20 min away, and Great Barrington/Stockbridge were easily accessible for day trips. We plan to come back for skiing, and to take advantage of the lake activities in the summer. The only downside was the busy road, as mentioned in the listing, but the traffic quieted down in the evening and it didn't affect our sleep at night with the bedrooms located in the back of the house (husband is a very light sleeper; we did bring and use sound machines just in case).

Private Lakehouse in the heart of the Berkshires
I want to say thank you to Christopher and his family for allowing my friends and me to stay in their home. it was clean, beautiful, serene and exactly what it was described to be. Christopher, your suggestions on golf courses for my friends and me were exceptional. I hope we were as good of guests as you were hosts!

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
Great place to spend quiet time with loved ones and enjoy nature!

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
I cannot thank Joyce enough for opening her lovely home to us. We felt relaxed and refreshed from the minute we arrived. Whether it was sipping coffee and reading by the pond or watching our beagle explore the grounds, I don't think the smile left my face. Joyce was so helpful with recommendations and available to answer any questions we might have had. The proximity to Great Barrington and Stockbridge was fantastic but the local Hillsdale attractions should be missed. We'll absolutely stay here again! Love this house.

Plan your Berkshires by the lake
I cannot emphasize enough how responsive, helpful and accommodating Julie was before and during our stay. The property is as shown, interior was clean and beds very comfortable. The walk to the lake is a short, peaceful one. It is a lovely setting with quiet neighbors. Highly recommend for anyone visiting nearby Berkshire attractions or for a quiet getaway near a beautiful lake!

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.

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

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!
Sarah was a wonderful host! She was very responsive and helpful throughout our stay. The cabin was cozy and nestled in the woods. The space was clean and had all the amenities to feel like home away from home. The location was great, too. Despite its’ remote feel, it was conveniently nestled about 20 minutes between other Berkshires towns such as Great Barrington, Lenox, Lee, Stockbridge, etc. Overall, we had a wonderful experience and highly recommend a stay in this cozy home.

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!

The Cosmo Cottage
look forward to renting again 4 sure

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!
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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
- Hartford Golf Club
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Opus 40
- Naumkeag
- Brignole Vineyards
- Bousquet Mountain Ski Area