Vacation rentals with a kayak in Cheshire County

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Top-rated kayak rentals in Cheshire County

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Top guest favorite
An outdoor tub is situated on a wooden deck, surrounded by vibrant autumn foliage. A red faucet provides a natural flow of water, while a small bowl of floating objects rests nearby. In the background, a glimpse of a serene lake can be seen through the trees.
Cabin in Stoddard
4.99 out of 5 average rating, 155 reviews

Boulder House - Extraordinary Luxury in the Woods!

From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

Top guest favorite
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, 125 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.

Top guest favorite
A wooden dock extends over calm waters, featuring four white Adirondack chairs positioned for lake views. In the background, a blue house is nestled among lush greenery, with large windows reflecting natural light. The scene illustrates a peaceful lakeside setting.
Home in Fitzwilliam
5 out of 5 average rating, 16 reviews

Lakefront Home | Near Monadnock

Welcome to our peaceful oasis on Laurel Lake - one of the cleanest lakes in New Hampshire! If you're looking for a place to relax after hiking Mount Monadnock or to have a week of summer fun with the family this is the home for you. Enjoy your morning coffee on the deck overlooking the lake, spend your day kayaking and end it with an outdoor shower before laying in bed listening to the sounds of the loons. Enjoy local activities like hiking, breweries, berry picking and visiting scenic towns!

Guest favorite
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
4.85 out of 5 average rating, 149 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!

Top guest favorite
A contemporary lakefront home is surrounded by trees, featuring large windows that reflect natural light. A spacious deck extends along the side, offering views of the water. The building's exterior is finished in grey tones, complementing the serene landscape.
Home in Stoddard
5 out of 5 average rating, 18 reviews

Modern Lakefront Home

Relax with the whole family at this peaceful lakefront home. Enjoy breakfast overlooking the lake or read a book while listening to the soothing sound of water flowing over the dam. Located at the Southern end of Highland Lake there is little boat traffic. Enjoy the water for swimming, paddle-boating, kayaking or fishing. Leaf peeping in the fall or skiing, snowmobiling or ice fishing in the winter. Great location for large families or multiple families to get together and enjoy the day.

Guest favorite
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, 144 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 favorite
Home in Chesterfield
4.9 out of 5 average rating, 135 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 favorite
Chalet in Rindge
5 out of 5 average rating, 47 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 favorite
A fire pit table is positioned on a deck, surrounded by two chairs. Flickering flames emerge from the center, creating a warm ambiance. In the background, a serene pond is framed by trees, with seating and recreational equipment visible along the water's edge.
Home in Rindge
4.98 out of 5 average rating, 47 reviews

Divol Pond Cabin

Family friendly rustic style interior home tucked away on a private dead end road. Small private pond with only three houses with access. Stunning deck with waterview connected to master bedroom with cathedral ceiling and skylights. Small fire pit. Grill. Dual heat propane fire pit table. Dock, kayak, paddle boat, hammock. Mount Watatic five minutes away. Mount Monadnock 20 minutes away. Restaurants, grocery stores/shopping close by. Perfect place to relax and enjoy quite times of nature.

Top guest favorite
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, 262 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 favorite
Home in Stoddard
4.97 out of 5 average rating, 29 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!

Top guest favorite
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.
Guesthouse in Stoddard
5 out of 5 average rating, 16 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!

Popular amenities for Cheshire County kayak rentals