Vacation rentals with a kayak in Berkshire County

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Popular amenities for Berkshire County kayak rentals

House rentals with a kayak

Top guest favorite
Home in Sandisfield
5 out of 5 average rating, 33 reviews

Waterfront oasis in heart of Berkshires

LisaRating, 5 stars2 weeks ago
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
Guest favorite
Home in Becket
4.92 out of 5 average rating, 78 reviews

Little Longbow Lakefront Chalet

PeterRating, 5 stars2 months ago
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
Guest favorite
Home in Becket
4.96 out of 5 average rating, 26 reviews

New Shaw Pond Skytop Retreat in the Berkshires

NancyRating, 5 stars5 months ago
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).
Guest favorite
Home in Pittsfield
4.95 out of 5 average rating, 62 reviews

Summer Family Fun at Hygge House on Richmond Pond

KatrinaRating, 5 stars8 months ago
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.
Guest favorite
Home in Becket
5 out of 5 average rating, 15 reviews

Private Lakehouse in the heart of the Berkshires

DanRating, 5 stars6 months ago
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!
Guest favorite
Home in Becket
4.94 out of 5 average rating, 32 reviews

Lakefront Cottage on Private Beach

GillianRating, 5 stars1 month ago
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 😊
Guest favorite
Home in Becket
4.93 out of 5 average rating, 27 reviews

Lakefront Jewel By: Evergreen Home

BraidyRating, 5 stars4 days ago
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!
Guest favorite
Home in Becket
4.97 out of 5 average rating, 35 reviews

Secluded lakeside charmer

LaurenRating, 5 stars3 days ago
We had the most relaxing and peaceful few days. Beautiful home! Such a thoughtful host. Lovely bottle of wine and goodies waiting for us with a nice personal note welcoming us. The photos show exactly what the house is like. The screened in porch was a great spot to read and to eat dinner. The visiting deer, geese and beaver were fun to watch. Kayaking was wonderful! Lots of hiking in the area and so close to the Outlets, dining and other activities. We highly recommend this property for a quick getaway or a long vacation. Looking forward to visiting again!!

Cottage rentals with a kayak

Superhost
Cottage in Hillsdale
4.85 out of 5 average rating, 68 reviews

Secluded Country Getaway on 22 acres

BrandonRating, 5 stars3 days ago
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).
Guest favorite
Cottage in Canaan
4.9 out of 5 average rating, 137 reviews

Plan your Berkshires by the lake

HannahRating, 5 stars3 days ago
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.
Cottage in Monterey
4.79 out of 5 average rating, 14 reviews

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

PaulRating, 5 stars10 months ago
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.
Guest favorite
Cottage in Becket
4.81 out of 5 average rating, 54 reviews

Cozy Cottage on the Lake

PaigeRating, 5 stars5 months ago
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.
Top guest favorite
Cottage in Otis
5 out of 5 average rating, 17 reviews

Lake Escape: Lakefront Cottage in the Berkshires

JeanneRating, 5 stars8 months ago
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.
Guest favorite
Cottage in New Marlborough
4.9 out of 5 average rating, 39 reviews

Pet friendly Cottage on Lake; Hike, Swim, Kayak

KunalRating, 5 stars2 months ago
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 !
Top guest favorite
Cottage in Lanesborough
5 out of 5 average rating, 20 reviews

Norte Maison 2 beds 2 Baths Minutes to Jiminy Peak

CherylRating, 5 stars3 weeks ago
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!
Cottage in Hinsdale
4.7 out of 5 average rating, 10 reviews

Modern one bed room cottage loft on beautiful Lake

AdrienneRating, 5 stars22 months ago
The setting on the lake was just gorgeous, and the accommodations were immaculate. It is definitely off the beaten path but within driving distance to Berkshires attractions like Tanglewood, museums etc. If it’s R&R you’re seeking, then this is the place for you!

Cabin rentals with a kayak

Superhost
Cabin in Otis
4.81 out of 5 average rating, 21 reviews

Simple, rustic, cozy get away

ChrisRating, 5 stars9 months ago
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!
Guest favorite
Cabin in Lanesborough
4.98 out of 5 average rating, 47 reviews

Glamping in the Berkshires w/ car charging station

NancyRating, 5 stars2 weeks ago
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.
Cabin in Becket
5 out of 5 average rating, 3 reviews

Berkshires Treehouse Retreat- Lake access!

JudyRating, 5 stars3 days ago
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
Cabin in Stockbridge
4.71 out of 5 average rating, 34 reviews

Cozy Stockbridge Cabin - Walk to Beach & Lake!

Teresa PrinsterRating, 5 stars20 months ago
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.
Guest favorite
Cabin in Becket
4.86 out of 5 average rating, 113 reviews

Wildlife Retreat in the Forest

DiegoRating, 5 stars1 month ago
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.
Superhost
Cabin in Otis
4.87 out of 5 average rating, 54 reviews

Enjoy 43 Acres on Two Ponds!

PatrickRating, 5 stars1 month ago
We had a great stay for my daughter’s college graduation. Really enjoyed the house and fire pit. Thanks!
Cabin in Austerlitz

The Cosmo Cottage

BrianRating, 5 stars1 week ago
look forward to renting again 4 sure
Guest favorite
Cabin in Canaan
4.99 out of 5 average rating, 72 reviews

Beautiful Lake Front Cabin

LouiseRating, 5 stars10 months ago
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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