Vacation rentals with a kayak in The Berkshires

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Popular amenities for The Berkshires kayak rentals

House rentals with a kayak

Top guest favorite
The exterior of the lakefront home showcases a vibrant blue facade, framed by well-maintained green lawns and leafy trees. A spacious deck is visible, along with multiple large windows that enhance the inviting appearance of the property.
Home in Valatie
5 out of 5 average rating, 114 reviews

Escape to Lakefront Leisure—Amazing views!

AndrewRating, 5 stars1 month ago
Had a great time with friends for the weekend. Beautiful view of the lake and plenty of space. Everything is labeled in the kitchen so you can easily find everything you need!
Guest favorite
The exterior of a modern house is illuminated by warm lights during twilight. Large windows and multiple balconies showcase the architecture, surrounded by trees and natural greenery. A gravel path leads towards the house, enhancing the inviting ambiance of the mountain setting.
Home in Mount Tremper
4.96 out of 5 average rating, 102 reviews

Chef's kitchen, seclusion, and breathtaking views

JeffRating, 5 stars3 weeks ago
This is our third year in a row staying here and every year it’s better than the last. The best host(s) we’ve ever had and the house is amazing. We highly recommend this property.
Superhost
A wooden dock extends over the calm waters of Lake Garfield, featuring two rustic chairs and a small table. Lush trees surround the lake, with a blue sky above dotted with clouds, creating a serene outdoor space for relaxation.
Home in Monterey
4.82 out of 5 average rating, 79 reviews

Rustic 3bd Lake Front Country Cottage

EdwardRating, 5 stars3 weeks 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 favorite
Home in Coventry
4.98 out of 5 average rating, 110 reviews

Cozy cottage 5 minutes from UConn

TiffaniRating, 5 stars1 week ago
Wonderful and peaceful stay for a relaxing girls weekend. Outstanding clean and comes with everything you may need. The space is kid friendly, and extremely beautiful. Would definitely stay again.
Guest favorite
The interior space features a white armchair beside a decorative wooden stool and a black coffee table. A tall ladder leads to the lofted area, while a metal shelving unit displays a framed image of a cow and a plant. Exposed wooden beams complement the natural decor.
Home in Egremont
4.94 out of 5 average rating, 81 reviews

Modern and Stylish Country Lakeside Cottage

NikiRating, 5 stars1 week 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 favorite
A covered porch features comfortable seating with soft cushions, offering expansive views of the lake and surrounding trees during sunset. The warm light casts a golden hue, enhancing the serene outdoor space, while a small table sits in the center, inviting relaxation.
Home in Pine Plains
4.98 out of 5 average rating, 123 reviews

Twin Island Lake House • Hot Tub

KaiRating, 5 stars2 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 favorite
An open living space features a combination of modern seating options, including a gray armchair and a green accent chair. A circular ottoman and cozy patterned rug add warmth. Bar stools are positioned at the kitchen counter, while large windows allow ample natural light.
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.
Guest favorite
A view from the second-floor deck showcases a serene landscape with a lake surrounded by trees. The grassy yard leads to a road, with glimpses of neighboring homes visible across the water. A partly cloudy blue sky adds brightness to the tranquil scene.
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).

Cottage rentals with a kayak

Guest favorite
A dining area offers a wooden table surrounded by black chairs, with large windows overlooking the lake. Slate flooring complements the bright, airy space, creating a seamless connection to the outdoor views. Natural light fills the room, enhancing the serene ambiance.
Cottage in Putnam Valley
4.96 out of 5 average rating, 164 reviews

Private Lake House 1 Hour to NYC & Near Westpoint

LoriRating, 5 stars3 days 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.
Guest favorite
Cottage in Orange
4.91 out of 5 average rating, 185 reviews

The Lake Cottage: A Sweetwater Stay

CourtneeRating, 5 stars3 weeks 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 favorite
A light-filled living area features a gray sofa adorned with patterned cushions. A wooden coffee table rests on a colorful rug, with a sleek arc lamp illuminating a cozy reading chair nearby. Large windows provide views of the surrounding trees, enhancing the natural ambiance.
Cottage in Poughkeepsie
4.91 out of 5 average rating, 352 reviews

Be in Nature at this Gorgeous Riverfront Cabin

BernardoRating, 5 stars1 week ago
I stayed at this place for my husband's birthday, The house is beautiful and very quiet, I loved the interior and the view. The only things you need to be aware is the AC is located in the living room, inside the room you need to use fans or leave the door open
Top guest favorite
An aerial view captures a cozy cottage surrounded by lush greenery, featuring large windows that glow warmly in the evening light. A stone patio is visible, with outdoor seating and a fire pit. Nearby, a well-maintained lawn and a parking area with vehicles can be seen.
Cottage in Guilford
4.99 out of 5 average rating, 102 reviews

Waterfront Joshua Cove Cottage with private beach.

ConnorRating, 5 stars2 weeks ago
Our 2 day stay at the cottage was just what we’d hoped for our wedding weekend! Annalisa was so responsive and accommodating. A wonderful host, such wonderful hospitality and an amazingly stunning private retreat! Would definitely return!
Superhost
A tranquil lakeside area features a private dock with lounge chairs and an umbrella, providing a place to relax by the water. Nearby, a wooden deck leads to the charming cottage, surrounded by lush greenery and trees, creating a serene atmosphere.
Cottage in Red Hook
4.9 out of 5 average rating, 206 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

JenniferRating, 5 stars2 weeks ago
Thank you Ellen for the easeful stay at your cottage with clear instructions. The surroundings are beautiful. We saw an eagle at the lake!
Top guest favorite
A cozy cottage is shown nestled among trees, featuring light-colored siding and green trim. Colorful flowers and shrubs surround the entry, while a serene lake is visible in the background, reflecting the greenery and sky.
Cottage in Gloversville
4.93 out of 5 average rating, 123 reviews

Peaceful "Sleepy Loon Cottage" on Lake Edward ADK

AlfredRating, 5 stars4 days ago
Lori and Mark are great hosts, very quick communication and always ready to answer any question you may have. The cabin was nice and clean and had all the things needed for a great stay. Great kayaks to take to the water. All in all just a great spot to hang out for a few days.
Top guest favorite
The newly renovated house is set against a backdrop of trees, featuring a charming exterior with grey siding and a brick chimney. A small porch is visible, and colorful autumn leaves are scattered across the front yard, enhancing the welcoming appearance.
Cottage in Colchester
4.97 out of 5 average rating, 174 reviews

Lakefront peaceful getaway cottage

JamesRating, 5 stars2 weeks ago
What a wonderful and peaceful location! Doreen was very responsive and exceptionally helpful. The pictures are spot with a very clean and well stocked home. Amazing views from the bedroom and second floor deck. Amazing place to fish, kayak, and just enjoy the scenery! Enjoyed hiking nearby, great food in the area and a very scenic location to relax.
Guest favorite
Sunlight emerges over a tranquil lake, casting golden hues across the water. Tall trees frame the scene, with dense greenery surrounding a wooden deck. The sky displays a blend of soft blues and whites, creating a peaceful natural ambiance.
Cottage in Putnam Valley
4.89 out of 5 average rating, 271 reviews

Lakefront Cottage near Hudson Valley

BrianRating, 5 stars1 month ago
Stayed for a long weekend with my wife and two dogs. Cottage was comfortable and clean with an amazing view of the lake with a nice patio and access to the dock which we enjoyed. Also great location just a bit over an hour from the city but within a 15 minute drive to many great hikes and close to many great food options. Tony was also very responsive and helpful with recommendarions. Highly recommend.

Cabin rentals with a kayak

Guest favorite
The lakefront cabin is framed by lush greenery, with a blue exterior and multiple large windows reflecting onto the calm water. A wooden dock extends toward a turquoise kayak, surrounded by tall trees, creating a serene and inviting atmosphere.
Cabin in Ferndale
4.92 out of 5 average rating, 221 reviews

Charming Catskills Lakefront Home—2 hrs from NYC!

MatthewRating, 5 stars5 days ago
We had a great time at Jill’s place! The house had everything we needed and was super clean. The views out to the lake were beautiful and the paddle boards were a lot of fun! The nearest grocery store is about 8 minutes away, and the town of Liberty isn’t much further. The check in process was easy, and Jill is a great and responsive host. Also, there’s a sweet vinyl collection with a great sound system! Would definitely stay again!
Guest favorite
The exterior of the cabin is showcased, featuring large, arched windows that reflect surrounding trees. A wooden deck with green Adirondack chairs offers space for relaxation. The warm wood siding blends harmoniously with the natural landscape.
Cabin in Hoffmeister
4.86 out of 5 average rating, 107 reviews

Cabin on the Creek - cozy & private

LouiseRating, 5 stars3 weeks 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!
Superhost
The cabin is softly illuminated by outdoor string lights at dusk, creating a welcoming atmosphere. A stone pathway leads to a fire pit surrounded by four Adirondack chairs, while the cabin's deck features inviting seating. Lush trees provide a natural backdrop.
Cabin in Smallwood
4.96 out of 5 average rating, 136 reviews

Lake Access•Canoe•Paddle Boards•Renovated•BBQ

AriRating, 5 stars2 days ago
Really charming cottage in the woods, and great, responsive hosts. Really had a nice time in this wooded and rural area, with two lakes nearby and the canoes on white lake. The cottage was clean and had a sleek, minimalist, scandanavian style (I felt like I was back in Sweden from years ago), which we appreciated! very peaceful at night and the AC worked great which helped out greatly on the hot days we were there. It's close enough to Woodstock museum/grounds, good food and laid back entertainment options in neighboring towns. Overall, a great stay, thank you!
Guest favorite
A wooden dining table is set near the water with benches surrounding it. A potted plant sits at the center of the table. In the background, a tranquil lake can be seen, bordered by trees and a dock. Soft sunlight filters through a canopy overhead.
Cabin in Stamford
4.95 out of 5 average rating, 137 reviews

ROMANTIC LAKE-FRONT Rustic Cabin by NYC Designer

GenevieRating, 5 stars3 months ago
The cabin is a great place for couples and families, loved the layout, very cozy with great views of the lake. Went ice fishing on the lake, caught lots of bass. Spent mornings and evenings warming up next to the pellet stove, drinking tea enjoying the views. We had a great time, would love to come back in the summer.
Guest favorite
An aerial view captures the lakefront cabin nestled among lush greenery, surrounded by expansive trees. The property features a private dock extending into the water, with neighboring cabins displaying varied architecture in the serene landscape.
Cabin in Athens
4.94 out of 5 average rating, 101 reviews

Charming Lakefront Cabin with Hot Tub

EimearRating, 5 stars1 week ago
We had an amazing time at Ruth’s home and we loved the cabin feel. Between the hot tub, lake, and lawn games our time went by so quickly. The home was very clean and had all the essentials. We will definitely be back again!
Top guest favorite
The cozy living area features a rustic stone fireplace surrounded by wooden paneling. A rocking chair is positioned nearby, complemented by a colorful cushion. Large windows let in natural light, and a fire extinguisher is discreetly placed for safety.
Cabin in Kingston
5 out of 5 average rating, 211 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.
Guest favorite
Cabin in Monticello
4.93 out of 5 average rating, 134 reviews

Cozy Catskills Cabin

RuthRating, 5 stars2 weeks ago
From the moment we walked in we felt so at ease and at home. It is completely updated and looks like it a professional interior decorator designed it. The pictures don't do it justice. About 5 min from Bethel Woods which was fantastic. Would recommend this beautiful home 100%.
Top guest favorite
An open-floor-plan great room features a large dining table surrounded by natural wooden beams and modern furnishings. Skylights illuminate the space, highlighting a cozy seating area with a blue couch and fireplace. The kitchen area is visible in the background, enhancing the communal feel.
Cabin in Catskill
4.91 out of 5 average rating, 236 reviews

Modern secluded Log Cabin in woods-great location!

AlstonRating, 5 stars1 month 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.

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