Vacation rentals with a kayak in Cheshire County

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Popular amenities for Cheshire County kayak rentals

House rentals with a kayak

Guest favorite
Home in Rindge
4.8 out of 5 average rating, 5 reviews

Lakefront family vacation home

KristenRating, 5 stars1 month ago
We had a wonderful stay at this home! Stephen and Toby were great hosts who were easy to work with. Some of the house has been renovated recently and is beautiful. The house was clean and the views were amazing! We would definitely stay here again.
Top guest favorite
Home in Nelson
5 out of 5 average rating, 14 reviews

The Boat House on Granite Lake

KirstenRating, 5 stars4 weeks ago
I had an absolutely wonderful stay at Granite Lake! The house is gorgeous—beautifully decorated, incredibly comfortable, and stocked with everything you could possibly need. Jennifer was an amazing and responsive host, making the entire experience extremely easy and welcoming. One of the highlights was the 3-mile loop around the lake, perfect for a run or walk. There are also kayaks for some time out on the water. Mornings and evenings should be spent on the porch—reading, sipping coffee or wine, and watching the stunning sunrises and sunsets. This place is truly a slice of peaceful paradise. I can’t recommend it enough and hope to return soon!
Guest favorite
Home in Rindge
4.94 out of 5 average rating, 35 reviews

Magic Lakehouse, Waterfront, Private Beach & Dock

DeborahRating, 5 stars3 weeks ago
beautiful setting on a lake. large deck and a beach area with a dock. kitchen is well stocked.
Top guest favorite
Home in Antrim
4.98 out of 5 average rating, 81 reviews

The Cozy Place

WayneRating, 5 stars1 day ago
Absolutely beautiful location, the lake is about 20ft from the back deck. Quiet, peaceful and sleeping with the slider open allows you to hear the loons; if you've never fallen asleep to the sounds of loons, this is reason enough to book a stay.
Superhost
Home in Winchendon
4.96 out of 5 average rating, 25 reviews

Amazing Lakefront Home with Pool- Tatum's Place

CamilleRating, 5 stars2 weeks ago
Our family getaway of 3 generations enjoyed the beautiful outdoors- between the magnificient pool, peaceful lake and the expansive yard where we were able to have fun playing the bocce set and cornhole game we brought. The outdoor seating kitchen area was perfect for gathering and so inviting for conversation and just relaxing. Ashley was easy to reach and responded to any questions.
Top guest favorite
Home in Washington
5 out of 5 average rating, 29 reviews

Nature Retreat: Kayaks, Hot Tub, SUP's & Fire Pit

Nicole ERating, 5 stars3 months 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!
Guest favorite
Home in Hillsborough
5 out of 5 average rating, 9 reviews

Very Private Cabin on 12 Acres

SamanthaRating, 5 stars3 weeks ago
Great place, very responsive and great communication, comfy and cozy definitely recommended! it was a wonderful get away.
Home in Fitzwilliam
5 out of 5 average rating, 3 reviews

Lakefront Home | Near Monadnock

JordinRating, 5 stars1 month ago
If I could give this 10 stars I would. This home is beautiful inside and out and perfect for a relaxing get away. The views are incredible and the home itself is clean, welcoming, and so comfortable. The host gave clear, concise instructions and there was no confusion or frustration with check-in/out. I loved this place and can’t wait to come back!!!

Cottage rentals with a kayak

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

Cheerful Lakeside Studio Cottage

LisaRating, 5 stars10 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 stars10 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 stars7 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 stars14 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 stars8 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 stars8 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, 4 reviews

Blacksmith Cottage on Spofford Lake

ElizabethRating, 5 stars1 day ago
We really enjoyed our stay at the cottage. The cottage was cozy and perfect for two, or a couple with kids. We did not know it did not have an oven but Ali provided us with the right tools to cook our dinner on the stovetop. The lake was steps away, but the weather did not accommodate swimming and kayaking. (Cannot control Mother Nature). It was an ideal location for our long weekend. The only downside was the highway noise. With the windows shut since it got chilly, it was fine. But morning one with windows open, it was noticeable. (But, we are accustomed to minimal noise at home). We are already thinking about a return next summer with a few family members being in neighboring cottages. And I did not mention the private beach which was fun to meet our neighbors and share happy hour with various kids playing in the sand and waves.
Cottage in Rindge
4.77 out of 5 average rating, 66 reviews

Lakeside Retreat – HOT TUB, Swimming, Boats & More

DrewRating, 5 stars7 months ago
Amazing scenery and an awesome weekend get away spot. Very thankful we found this place!

Cabin rentals with a kayak

Superhost
Cabin in Chesterfield

Farmhouse Cabin on Spofford Lake

FernandoRating, 5 stars3 weeks ago
Everybody loved the place, lean and peaceful. I would recommend visiting.
Guest favorite
Cabin in Washington
4.91 out of 5 average rating, 23 reviews

Highland Lake Waterfront Cabin

KatherineRating, 5 stars10 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, 139 reviews

Lakeside Log Cabin near Mt Monadnock

MaryRating, 5 stars2 days ago
We had a lovely stay at this cabin! Very quaint and beautiful location. Cabin was tastefully furnished and host was very responsive. Would stay here again. Thank you!
Top guest favorite
Cabin in Stoddard
4.98 out of 5 average rating, 103 reviews

Boulder House - Extraordinary Luxury in the Woods!

ClareRating, 5 stars2 weeks ago
My husband and I enjoyed a peaceful weekend away at the Boulder house. It is in a beautiful, quiet location and the house has everything you need to never want to leave. From walks around the wooded property, a canoe ride on the pond spotting beaver lodges, listening to the many different birds, to the hot bath on the deck means you can relax but not be bored, even on a rainy weekend. The host is very friendly and helpful and clearly takes pride in and care of his property. Check out was easy with minimal asked of us. The house is just as cool in person as in the pictures- lots of thoughtful details and such a unique, cozy space that is perfect for 2 people to relax in with high end kitchen amenities and comfortable furniture. We did check out the area while we were there and enjoyed the Harrisville General Store and an amazing dinner at the Hancock Inn. We definitely hope to return to this special spot again soon!
Guest favorite
Cabin in Stoddard
4.95 out of 5 average rating, 20 reviews

GiGi's Cabin/ 314' Shoreline

MichaelRating, 5 stars1 week ago
Fantastic! Great waterfront cabin with plenty of space. Would recommend for any group looking for a relaxing trip. The Jule team was a great host and super responsive. 10/10
Guest favorite
Cabin in Stoddard
5 out of 5 average rating, 8 reviews

2 Mi to Boat Ramp: Log Cabin in New Hampshire

SiobhanRating, 5 stars1 month ago
We had a great weekend stay here. Thank you!
Guest favorite
Cabin in Washington
4.94 out of 5 average rating, 33 reviews

Lakefront Log Cabin on 2 acres

GuilhermeRating, 5 stars3 weeks ago
Really amazing place, quiet and amazing view the cabin was also amazing
Top guest favorite
Cabin in Stoddard
4.97 out of 5 average rating, 163 reviews

Secluded Renovated Retreat Surrounded by Nature

AndrewRating, 5 stars1 week ago
A wonderful gem which combines the beauty and serenity of the natural surroundings with a masterfully renovated cabin with great layout and all you need for a great vacation. Don and Joyce are super hosts: responsive, friend and very hospitable.

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