Holiday rentals with a kayak in Cheshire County

Find and book unique kayak rentals on Airbnb

Top-rated rentals with kayak in Cheshire County

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

1 of 1 pages1 / 1
Top guest favourite
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, 161 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.

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, 81 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
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, 128 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 favourite
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, 17 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!

Top guest favourite
Chalet in Rindge
5 out of 5 average rating, 51 reviews

Cabin & Sauna on Lake Monomonac

Beautiful Finnish House and a Sauna on Lake Monomonac. 2 Queen bedrooms, full kitchen and bathroom. Maximum occupancy 4. Perfect for a family reunion, get together or event. Authentic Finnish wood burning sauna, boat dock, kayaks, canoes, nature, wildlife, birding, walking, running, hiking, biking, snow skiing ATV, UTV, snowmobiling. Close to Mt Monadnock, Mt. Wachusett, Pats Peak, Granite Gorge Mountain Peak, and Crotched Mountain for hiking and skiing. 1 hr. from Boston 4 hrs. from NYC

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
4.85 out of 5 average rating, 150 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
4.91 out of 5 average rating, 148 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
4.9 out of 5 average rating, 139 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.

Guest favourite
The open-concept living area features a vaulted wood ceiling, showcasing natural wood walls. A kitchen island with a marble countertop is positioned centrally, with a cozy seating area visible through large windows, providing a connection to the serene outdoor landscape.
Cabin in Rindge
4.98 out of 5 average rating, 163 reviews

Picturesque Log Cabin near Mt Monadnock

Welcome to Cabin at the Cove! This spacious 4-bedroom 2-bathroom log cabin sleeps 10 + up to 2 dogs. The cabin offers rustic charm with modern amenities and is located in the beautiful Monadnock region by Lake Contoocook! Vacation near a picturesque lake, hike to leaf peep from the top of beautiful Mount Monadnock, cross-country ski, or curl up with a book by the fire – there is something for everyone year-round. While only 90 minutes from Boston, it feels like a true nature escape.

Top guest favourite
Home in Stoddard
4.97 out of 5 average rating, 31 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 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, 18 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!

Top guest favourite
The yurt is nestled among lush gardens and trees, framed by vibrant greenery. Surrounding flowerbeds feature various plants, with a focus on a blooming flower in the foreground. A wooden picnic table is visible nearby, inviting outdoor relaxation.
Yurt in Stoddard
5 out of 5 average rating, 13 reviews

The Yurt Sanctuary!

Welcome to The Sanctuary! This yurt dwelling experience has been specially curated for you. Nestled on the edge of the woodlands and surrounded by gardens, the yurt has been a special place for our family for over a decade and we are excited to share this sacred space with you. Unplug, relax, and restore while taking refuge in the comfort of our property which has been cultivated by hand since 2005. Tap into the sounds of nature and find solace at The Yurt Sanctuary.

Popular amenities for kayak rentals in Cheshire County