Holiday rentals with a kayak in Cheshire County

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Top-rated rentals with kayak in Cheshire County

Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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Guest favourite
A charming exterior of the house is captured, featuring light-colored siding and a welcoming porch. Lush greenery surrounds the property, while a wooden well adds character to the front yard. Stone pathway leads to the entrance, enhancing the inviting atmosphere.
Home in Chesterfield
4.95 out of 5 average rating, 77 reviews

The River House

Take it easy at this unique and tranquil getaway on the Connecticut River. Large 2-tier deck with steps to private boat dock Jun 15-Oct 15 right on the river. Wake up to amazing views of the river with the stillness of nature around you. Superb water skiing with 18 miles of wide, deep river. Excellent fishing. A habitat for bald eagles. Boat launch nearby. Under 1 hr to major ski areas including Okemo, Mount Snow, Stratton and Magic Mountain. 15 min to Brattleboro Ski Hill. Granite Gorge 30 min.

Top guest favourite
Cabin in Stoddard
4.97 out of 5 average rating, 238 reviews

Cozy Comfort on 250 Acre Private Estate

If you’re looking for serenity, peace and quiet, you've found it, amidst a 250 acre private estate. On a lake at the end of a mile long driveway (well plowed in the winter) Is Snowshoe Cabin. Built in 1929 as the garage for "Lakefalls Lodge, it's been completed renovated into a luxurious, cozy home with modern amenities. Guests rave about "views of the snowy pond while you’re warm inside" from heated floors and a wood burning stove with free firewood. Spikes provided for wonderful winter walks.

Guest favourite
A serene lakeside view is presented, featuring a wooden dock extending over calm waters. The surface reflects surrounding greenery and a partly cloudy sky. A small gazebo is positioned near the water's edge, enhancing the tranquil outdoor setting.
Cottage in Rindge
4.79 out of 5 average rating, 75 reviews

Lakefront Escape•HOT TUB•Fishing •Swimming•Boats

Relax with the whole family at our Pearly lake cottage! Home is very clean, warm and cozy! Bedroom on the first floor has a queen bed and a crib. Second bedroom upstairs, offers two queen beds and has an AC in the bedrooms. The bonus room has two smaller bunk beds. Living room has a pull out couch. Kitchen is fully equipped. The place offers a grill, fireplace, two kayaks, canoe and a boat for your enjoyment! Monadnock State Park is only 15 min away with multiple hiking trails and great views

Top guest favourite
Sunset is seen through a row of trees along the lake, casting gentle reflections on the water's surface. A boat is visible in the distance, leaving ripples as it moves across the calm lake, while the sky transitions from blue to shades of orange and gold.
Home in Washington
5 out of 5 average rating, 124 reviews

Newer Home on quiet 200 acre lake - sleeps 6

Less than an hour from Manchester, Concord & Keene, this new home offers relaxation & year-round adventure. This lakefront property has a dock, with kayaks & paddleboards. You could also walk down the paved road to the neighborhood beach & swim platform. About 30 minutes to Pats Peak, Sunapee, or Crotched Mtn ski resorts. Beds for 6, 2 full baths, W/D, fully equipped kitchen, open living space, gas fireplace, water views, gas grill, parking, firepit, internet. We do not allow pets or smoking.

Guest favourite
The front of the cabin features a wooden exterior, accented by green trim around the door. An inviting screened porch with large windows is surrounded by lush greenery, creating a sense of privacy and serenity. A stone walkway leads to the entrance, enhancing the natural setting.
Cabin in Stoddard
4.84 out of 5 average rating, 147 reviews

Cozy Cabin with Lake Access

Our cabin is situated in a private, peaceful setting surrounded by trees. Inside you will find a timeless lake house decor and everything you need for a relaxing vacation. A 1/4 mile walk or drive brings you to our private community lake access and boat ramp on beautiful Highland Lake. We offer use of our 3 kayaks (2 single/1 tandem) located next to the boat ramp. Nearby are great hiking trails and quaint villages. This is a wonderful place to unwind and have a truly fun & relaxing vacation!

Guest favourite
An A-Frame cabin is set on a sloped hill, surrounded by trees. The cabin features a deck overlooking the water, with kayaks and a hammock visible on the lawn. A wooden dock extends into the pond, enhancing the serene outdoor setting.
Chalet in Antrim
4.9 out of 5 average rating, 142 reviews

Direct Waterfront A-Frame, Close to 3 Ski Areas!

My direct waterfront, year-round A-Frame cabin is 30 min to Mount Sunapee, 20 min to Crotched, and 15 min to Pat's Peak! It’s located on a small 32-acre pond near Franklin Pierce Lake with over 100 feet of waterfront. There is a 6 foot main dock to load kayaks, and a small fishing dock off to the side. The fishing on our pond gets rave reviews! The property sits on 1/3 of an acre, on a sloped hill. It's located between Keene and Concord, and nearby many great hiking and snowmobile trails

Guest favourite
Home in Chesterfield
4.91 out of 5 average rating, 133 reviews

Governer's Brook Camp - 2 Bedroom

Renovated camp, 800 sq ft, near Brattleboro VT & Lake Spofford NH. Hiking trails start at the backyard. I15 minutes to Brattleboro, 5 minutes to the boat ramp on Connecticut River, 15 minutes to Lake Spofford, and 50 minutes to Mt. Snow. Across the road is a (seasonal) tumbling waterfall and gorge called “the Devils Den”. The backyard leads to woodlands with miles of trails. Enjoy a relaxing evening by the firepit overlooking the brook. Or outdoor cooking on a propane grill. ...2 Kayaks.

Top guest favourite
Chalet in Rindge
5 out of 5 average rating, 43 reviews

Cabin & Sauna on Lake Monomonac

Beautiful Finnish House and a Sauna on Lake Monomonac. 2 bedrooms, sleeps 4+ people comfortably with a full kitchen and bathroom and outdoor shower. Dock and boat launch/ramp including canoes, kayaks and sports equipment. Beautiful clean lake for boating, fishing, skiing and swimming. Close to Mt Monadnock (2nd most hiked mountain in the world), Mt. Wachusett Pats Peak, Granite Gorge Mountain Peak, and Crotched Mountain for hiking and skiing. 1 hr from Boston airport and 4 hrs from NYC.

Top guest favourite
The cabin exterior features a wooden porch with multiple steps leading to the entrance. An American flag hangs from the building, while surrounding greenery and rocky terrain enhance the natural setting. The serene atmosphere is complemented by the nearby stream.
Cabin in Stoddard
4.82 out of 5 average rating, 261 reviews

Waterfront Cabin on Beautiful Highland Lake!

Quiet lake experience, especially on weekdays, to get away and reset your busy life! This historic renovated "boat house" comes with 2 kayaks for your use. The boathouse is two large rooms. One room has 2 queen and 1 single bed. The kitchen area also has a single bed. There is an outdoor shower and an indoor claw foot bath tub. There is a small private outdoor deck. Lots to do in the surrounding area, but most people don't want to leave this beautiful setting. (Pets are not permitted)

Top guest favourite
Home in Stoddard
4.96 out of 5 average rating, 26 reviews

Lake house getaway

Relax and unwind with the whole family at this peaceful location. There's room for everyone at this multi-level, year round lake house on the scenic Highland Lake. Launch your boat in the south end of the lake and tie it up right outside the house and enjoy all the fishing, tubing and cruising around this beautiful area. Pick blueberries at the house or hike nearby Pitcher Mountain for more! Bring your snow shoes or your cross country skis end enjoy this seven mile long lake!

Guest favourite
A serene lakeside view showcases a vibrant sunset, with hues of orange and purple reflecting on the calm water surface. A wooden dock extends into the lake, featuring a lone Adirondack chair. Tree silhouettes can be seen along the horizon.
Guest house in Stoddard
5 out of 5 average rating, 15 reviews

Lakeside Couple's Getaway

If you are seeking a fun couples getaway at a stunning lakeside retreat, then look no further. The natural and rustic charm of a crystal clear lake in the woodlands of New Hampshire offer you a chance to unwind and relax. Summertime offers swimming, kayaking, paddle boarding and much more! Your stay includes access to 1 double kayak and 2 paddle boards. Located just 10 miles outside of the charming historic town of Keene where you can find many great restaurants and shops!

Guest favourite
An A-frame chalet is illuminated at dusk, showcasing its triangular structure and charming front porch. Warm light spills from the windows, and twinkling string lights enhance the serene outdoor setting surrounded by trees.
Chalet in Stoddard
4.93 out of 5 average rating, 313 reviews

Highland Haus | Cozy 70s Aframe | Lake Access

Authentic 1975 A-frame chalet nestled in peaceful Stoddard countryside. This cozy cabin sleeps 5 with two wood stoves and full kitchen. Perfect rural retreat just 2 hours from Boston! Explore nearby hiking trails, swimming spots, and fishing areas. Summer bonus: complimentary canoe access! Highland Haus offers a tranquil escape with vintage charm. Note for winter visitors: Shedd Hill Road requires AWD/4WD due to steep terrain. Your cozy retro hideaway awaits!

Popular amenities for kayak rentals in Cheshire County