Holiday rentals with a kayak in Cheshire County

Find and book unique kayak rentals on Airbnb

Top-rated Accommodation with a Kayak in Cheshire County

Guests agree: these holiday homes with a 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, 170 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.

Outdoor spacesValueNearby

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

5.0 out of 5 average rating, 135 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.

ValueOutdoor spacesView

Top Guest favourite

Chalet in Rindge

5.0 out of 5 average rating, 52 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

LocationHospitalityKitchen

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

5.0 out of 5 average rating, 20 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!

Outdoor spacesLocationCleanliness

Top Guest favourite

A serene lake is depicted, framed by lush greenery and tall trees. Two kayakers are seen gliding across the calm water, with a quaint cottage visible along the shore. In the background, wind turbines are set against a scenic mountain backdrop and partially cloudy sky.

Cottage in Antrim

4.96 out of 5 average rating, 85 reviews

Modern Quiet Lakeside Retreat

Come relax at our newly renovated lakefront home on Gregg Lake! Our spacious and modern home is located on a quiet cove of this 200 acre lake that boasts a variety of fun water activities. Enjoy the use of our kayaks, paddle boards and peddle boat or try your luck at catching some local bass with our fishing rods! You will also love the scenic sunsets you can view from our large deck that overlooks the lake. Tons of amenities included so that we can make your stay comfortable and stress free.

ValueOutdoor spacesLayout

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, 155 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!

Outdoor spacesValueAccess

Top Guest favourite

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

5.0 out of 5 average rating, 19 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.

LocationOutdoor spacesAccuracy

Guest favourite

Home in Chesterfield

4.9 out of 5 average rating, 144 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.

ValueLocationAccess

Superhost

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, 155 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

ValueOutdoor spacesNearby

Top Guest favourite

A serene evening view of Granite Lake is showcased, with a vibrant sunset reflecting on the water's surface. Silhouetted against the colorful sky, a small dock is visible, extending into the lake, and a few boats can be seen leisurely floating in the distance.

Home in Nelson

5.0 out of 5 average rating, 29 reviews

The Boat House on Granite Lake

Welcome to "The Boat House" ~ your private getaway on pristine Granite Lake. Enjoy sunrises over the lake from the deck with your morning coffee. Spend the day on the lake kayaking, fishing or relaxing on your private dock. Three mile road around the lake for walking or biking. The area offers many hiking trails. Keene’s many shops and restaurants are only 10 minutes away. Ideal for small families, couples, or a girls night getaway! This house is right on the water with amazing views!

ValueLocationCheck-in

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.

Guesthouse in Stoddard

5.0 out of 5 average rating, 22 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!

LocationOutdoor spacesComfort

Guest favourite

The A-frame chalet is surrounded by colorful fall foliage, showcasing vibrant orange and yellow leaves. A canoe is positioned by the entrance, complementing the cabin's rustic facade with green accents. A carpet of fallen leaves blankets the ground, creating a serene outdoor setting.

Chalet in Stoddard

4.93 out of 5 average rating, 327 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!

ValueOutdoor spacesKitchen