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Vacation rentals with a kayak in Cheshire County

Find and book unique kayak rentals on Airbnb

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Popular amenities for Cheshire County kayak rentals

House rentals with a kayak

Superhost
Home in Rindge
5 out of 5 average rating, 3 reviews

Secluded lakefront vacation home

ClaudiaRating, 5 stars2 months ago
Beautiful home. Well kept. Hosts super accessible and very friendly. We felt like home and house is super cozy
Top guest favorite
Home in Antrim
4.97 out of 5 average rating, 79 reviews

The Cozy Place

LauraRating, 5 stars3 months ago
We had such a great time here even in the winter! Pats peak is 20 minutes away so we did some skiing and had a nice clean, warm home to come back to! Thanks Laura and Hanna!
Guest favorite
Home in Rindge
4.94 out of 5 average rating, 33 reviews

Magic Lakehouse, Waterfront, Private Beach & Dock

CarrieRating, 5 stars7 months ago
Our stay at the Magic Lake house was wonderful. There is plenty of room, it is very well stocked with games, books, toys, and yard games, and the lake was beautiful to kayak. We enjoyed cooking out, sitting by the fire pit in the evenings, and hanging out on the deck. Such a great place to visit with family. Hannah and Dave were very timely in sending information and answering any questions we had. We would definitely stay there again!
Superhost
Home in Winchendon
4.95 out of 5 average rating, 22 reviews

Amazing Lakefront Home with Pool- Tatum's Place

NidhiRating, 5 stars1 week ago
Great stay overall — just be mindful of seasonal comfort! We had a lovely time at this beautiful property — it’s well-maintained, peaceful, and has a lot of charm. The host was responsive and check-in was easy. Just a heads-up for future guests: the property has seasonal settings, so you’ll either get heat or A/C depending on the time of year, not both. It made things a bit uncomfortable during a weather transition, but manageable. Still, the beauty and uniqueness of the space definitely made up for it. Would recommend with that one caveat in mind!
Top guest favorite
Home in Rindge
5 out of 5 average rating, 37 reviews

Lake house on walking trail near mountain

KavanRating, 5 stars2 months ago
Our stay at was truly wonderful, and the place was absolutely beautiful. We visited during the winter, and the snow blanketing the area transformed everything into a picturesque winter wonderland. The accommodation itself was clean and spacious, providing us with a comfortable and relaxing retreat. The surrounding area offered plenty of wonderful things to do, making our stay even more enjoyable. Rindge's natural beauty, enhanced by the snowy landscape, created a magical atmosphere perfect for outdoor activities and scenic drives. Can't wait to visit again!
Top guest favorite
Home in Washington
5 out of 5 average rating, 28 reviews

Spring Getaway: Kayak & Unwind by Highland Lake

Nicole ERating, 5 stars1 month ago
Our stay at Angela's place was absolutely fantastic. The moment we walked in the home gave that warm cabin cozy feeling. We were impressed by the cleanliness and attention to detail. The place had everything we needed for a comfortable stay. Angela was incredibly responsive and helpful, and we would definitely stay here again!"
Top guest favorite
Home in Rindge
5 out of 5 average rating, 82 reviews

The Crowcroft House

JoyRating, 5 stars4 months ago
Family of four stayed for a week while visiting family. As I think one other review may have said, the description is accurate however the space is much more roomy than the photos would have you believe. Two full bathrooms, a washer and dryer, incredible kitchen, comfortable beds and a serene location all made this location an incredible space but the small, thoughtful touches like hair towels, cotton rounds/swabs/balls in the main bath made our stay exceptional.
Superhost
Home in Rindge
4.93 out of 5 average rating, 73 reviews

Charming Lake Front Home

DawnRating, 5 stars8 months ago
A great spot for R & R! We loved being right in the lake, great view, private and quiet, hiking, walking trails, kayaking! Plenty of room to spread out! Clean and all amenities supplied! We enjoyed family and friends through the week. Local to Mt Madanock.

Cottage rentals with a kayak

Cottage in Nelson
4.61 out of 5 average rating, 31 reviews

Cheerful Lakeside Studio Cottage

LisaRating, 5 stars8 months ago
The Cheerfull cottage, the property, and the lake were so much more pleasant and beautiful than we expected from the photos and description. The cottage was cute , clean, comfortable, and had everything we needed for a lovely getaway. John was promptly responsive and accomodating for a last minute request. We had an amazong time kayaking on the lake, exploring blueberry island, paddling around in floats, and swimming in the super clean refreshing water by the dock. We sat in comfy adirondack chairs and enjoyed a campfire while watching the beatiful lake each night. We also got food in two superb restaurants - Papagallos for Italian, and the Farm Cafe for vegan.....both sooo good! All in a a great stay. Wewould definately come back!
Cottage in Nelson
4.9 out of 5 average rating, 29 reviews

Waterfront Cottage on Granite Lake near Keene, NH

TracyRating, 5 stars8 months ago
house and neighborhood, was quiet, relaxing, peaceful. The lake was beautiful. private side yard with firepit was enjoyed kayaking was so pleasant in the beautiful surroundings of the lake. We all.agreed we could not get any close to the lake, and will be again next year.
Guest favorite
Cottage in Chesterfield
5 out of 5 average rating, 5 reviews

Tiny Cottage on Spofford Lake

LeenaRating, 5 stars6 months ago
Such a cute cottage! The cottage was clean and the beachfront was beautiful. Ali was very responsive and helpful. Great stay!
Top guest favorite
Cottage in Putney
5 out of 5 average rating, 44 reviews

Woods Cottage-Private cheerful two bedroom cottage

KaraRating, 5 stars13 months ago
Ron & Priscilla are fabulous hosts! Extremely friendly and kind. They really went above and beyond to make sure we were safe and having a good time. They saved us from a winter snow storm AND a black out! They even came by to clear the snow on the path from the car to the house. The amount of things they did to make sure we were comfortable was really above and beyond. We felt right at home. The house was cozy and comfortable. The area is private, quiet and the surrounding area is beautiful. I would highly recommend anyone to stay with them. If we had more time off, we wouldn’t hesitate to go back! They really made our stay special.
Superhost
Cottage in Chesterfield
5 out of 5 average rating, 3 reviews

Cottage on Spofford Lake “Barn”

ChristopherRating, 5 stars6 months ago
The cabins were terrific. We had three cabins as a group. They are across the street from Spofford Lake, which has a small beach and a dock. We had a terrific night hanging out on the beach while lighting a fire in the pit. We had a great visit at Copper Cannon Distillery (located down the road) and went on a few hikes.
Superhost
Cottage in Chesterfield
5 out of 5 average rating, 3 reviews

Cottage on Spofford Lake “Library”

LynnRating, 5 stars7 months ago
We had a lovely time at the Library cottage, sitting on the porch, walking the grounds. Nice to spend time right on the beach that has Adirondack chairs and a fire pit. Our host Ali was always available and helpful. The bunk bed layout was a surprise, but worked out fine. We’d love to come back, maybe even in the summer. Thank you Ali for a welcoming stay.
Superhost
Cottage in Chesterfield
5 out of 5 average rating, 3 reviews

Blacksmith Cottage on Spofford Lake

ArlindaRating, 5 stars6 months ago
Loved Ali’s cabin ! Small and cozy, has all you need. Ali was super responsive and clear. Would love to stay again.
Top guest favorite
Cottage in Jaffrey
4.97 out of 5 average rating, 30 reviews

The Boathouse - A rustic and cozy lakeside cottage

HughRating, 5 stars7 months ago
The Boathouse is a jewel! Not only is one visited each morning with beautiful vistas, but the sense of peace is the spirit of the place. We had all we needed. Chris is a generous host who cares about the place and the guests.

Cabin rentals with a kayak

Guest favorite
Cabin in Washington
4.91 out of 5 average rating, 23 reviews

Highland Lake Waterfront Cabin

KatherineRating, 5 stars8 months ago
We had a wonderful time! Great location and super comfortable home with everything you need. Our 3 teenagers had a blast hanging out on the lake, around the campfire and playing video games. Relaxing on the porch in the morning with a coffee and looking over the lake was an added bonus. We'll definitely be back!
Guest favorite
Cabin in Rindge
4.98 out of 5 average rating, 133 reviews

Lakeside Log Cabin near Mt Monadnock

MiriamRating, 5 stars1 week ago
This cabin was great for a family getaway! Rindge has a lot of outdoor activities in the area and the house is 30 minutes from bigger towns if you need more stimulation. This was a great getaway for my family; the house had all the amenities. We were able to cook, do laundry, play games and watch movies with the kids. We did a scavenger hunt using some local landmarks - Emily provided a guide of things to do in the area so we could plan our itinerary in advance. Emily is a great host, I couldn’t have asked for better. 10/10 recommend!
Top guest favorite
Cabin in Stoddard
4.98 out of 5 average rating, 91 reviews

Boulder House - Extraordinary Luxury in the Woods!

TristaRating, 5 stars2 weeks ago
I had a comfortable stay at the Boulder Cabin. It felt like a luxurious, modern experience right in the middle of nature with plenty of supporting business' a short drive away. Thoughtful touches throughout that make being away from home a very worthwhile experience. I felt very supported while I was there and fortunate to experience the beauty of surroundings. Daily walks around the pond, leading to a waterfall, covered bridge, ducks, gardens; it was an unexpected perk that made this experience one to remember.
Guest favorite
Cabin in Stoddard
4.94 out of 5 average rating, 17 reviews

GiGi's Cabin/ 314' Shoreline

DianaRating, 5 stars6 months ago
Took my family for a fall getaway to the cabin. Everyone loved it. The room with the lake view was my favorite, although it is definitely a summer room as it does not have windows. Great for big families. Very private and peaceful. You cannot beat a lake side stay. We played Rummikub for 3 hrs one night! Left with many forever memories. Thank you!
Guest favorite
Cabin in Stoddard
5 out of 5 average rating, 5 reviews

2 Mi to Boat Ramp: Log Cabin in New Hampshire

WilberRating, 5 stars1 month ago
It was an unforgettable experience. A very beautiful place to rest with the family. I recommend it.
Guest favorite
Cabin in Washington
4.96 out of 5 average rating, 28 reviews

Lakefront Log Cabin on 2 acres

LamarieRating, 5 stars1 month ago
My stay was great I enjoyed the cabin but I wish the pictures were a little more accurate with the room sizes. Overall it was a great stay
Top guest favorite
Cabin in Stoddard
4.98 out of 5 average rating, 203 reviews

Cozy Comfort on 250 Acre Private Estate

TristaRating, 5 stars2 weeks ago
Snowshoe cabin is so charming! I really loved my stay in this cozy little cabin. We got a few mornings of snow, which made it all the more idyllic. The heated floors, covered porch, and view of the pond really stand out. I felt very safe and comforted while being there. The vintage touches throughout were well appointed, and the modern up to date features were appreciated in contrast. I would definitely return and recommend this to anyone who loves a charming cabin that feels like being wrapped up in a warm blanket

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