Vacation rentals with a kayak in Cheshire County

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Top-rated accommodations with a kayak in Cheshire County

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

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Top guest favourite

Cabin in Stoddard

4.98 out of 5 average rating, 110 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 favourite

Home in Washington

5 out of 5 average rating, 108 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

Cabin in Washington

4.94 out of 5 average rating, 36 reviews

Lakefront Log Cabin on 2 acres

Discover the perfect getaway at our Highland Lake lakefront cabin, set on 2 picturesque acres in peaceful rural New Hampshire. Just under 2 hours from Boston, this retreat boasts beautiful wood accents throughout, offering a cozy and rustic feel. Enjoy endless summer activities like swimming, boating, dirt biking, and fishing. In winter, the lake transforms for snowmobiling and ice fishing. Ideal for nature lovers and adventure seekers, our cabin promises relaxation and unforgettable memories.

Guest favourite

Cabin in Stoddard

4.84 out of 5 average rating, 135 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!

Superhost

Home in Chesterfield

4.91 out of 5 average rating, 116 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

Home in Nelson

5 out of 5 average rating, 16 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!

Top guest favourite

Home in Hillsborough

5 out of 5 average rating, 11 reviews

Very Private Cabin on 12 Acres

Are you looking for a private escape? Love to ride your ATV or snowmobile directly from where you are staying? Then you'll love our renovated cabin on 12 private acres. Fire pit in front with great views, large deck in the back with a grill. Bring your pets and children! The house is on a 12 acre parcel located near the end of a dirt road that directly connects to snowmobile and ATV trails. And a large sandpit you can ride to right from the house on your 4 wheeler or dirtbike. FUN!

Top guest favourite

Home in Chesterfield

4.95 out of 5 average rating, 58 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 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 1/4 mile away. 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.

Guest favourite

Chalet in Antrim

4.94 out of 5 average rating, 110 reviews

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

My year-round A-Frame cabin is 30 min to Mount Sunapee, 20 min to Crotched, and 15 min to Pat's Peak! It’s on a small 32-acre pond in New Hampshire. It is truly heaven on earth. There is over 100 feet of direct waterfront. There is a 6 foot main dock, and a small fishing dock off to the side. The fishing on our pond gets rave reviews! Most people catch and release, but please follow NH fishing laws: 16+ needs a license. The property sits on 1/3 of an acre, on a sloped hill.

Guest favourite

Chalet in Stoddard

4.95 out of 5 average rating, 273 reviews

Highland Haus AFrame Lake Access Vintage 70s Charm

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!

Guest favourite

Home in Harrisville

4.94 out of 5 average rating, 16 reviews

Harrisville Lake House - A Tranquil Get-Away

Welcome to Harrisville Lake House, a tranquil lakeside retreat for family and friends on the shore of Harrisville Pond. Our home is perfect for a week-long escape, where nature’s beauty meets the warmth of a family home. Our home is a treasure trove of antique furniture, worldly keepsakes, and artwork. Fall colors in September and early October are breathtaking! From the haunting call of loons to the majestic flight of bald eagles, nature is a daily delight!

Top guest favourite

Home in Rindge

5 out of 5 average rating, 27 reviews

Changes in Attitude

Nestled in the Monadnock region of New Hampshire, our charming cottage offers the perfect retreat for those seeking tranquility and outdoor adventures. Situated a short stroll from both Contoocook Lake and River, you can head out the front door and load up the beach cart for a short walk to the small neighborhood beach for a relaxing swim and sun or the back door for a walk on the trail to the river to use the canoe or kayaks or to walk on the trails.