Vacation rentals with a kayak in Cheshire County

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Top-rated kayak rentals in Cheshire County

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Guest favorite

Tiny home in Bennington

4.91 out of 5 average rating, 11 reviews

Waterfront Tiny Horse Trailer

Cozy up in an authentic and pristine former horse trailer tucked in a private, picturesque setting, overlooking the waterfront. Escape the daily grind. Experience nature's tranquility and quality time with the people you love! Paddle to the island for a picnic lunch. Canoes, kayaks and more are all on site. Swim, Fish, or just relax in the sun and never leave the property. Get mesmerized by the firepit, share stories and s’mores. Sip cocktails by sunset in the hot tub overlooking Mt. Monadnock.

Top guest favorite

Home in Washington

5 out of 5 average rating, 101 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

Cabin in Stoddard

4.97 out of 5 average rating, 157 reviews

Secluded Renovated Retreat Surrounded by Nature

Get away from it all in a secluded, yet modern cabin, which guests have loved for its "silence and beauty" and called "peaceful" and "serene". Located on the Lakefalls Estate, which maintains the roads, Mended Oar features heated floors throughout, a well-furnished kitchen with quality appliances and equipment, and luxurious linens. Hike the many trails outside the door on the snowshoes you'll find, then come inside to enjoy the wood burning fireplace (wood provided) and play a board game.

Guest favorite

Home in Washington

4.92 out of 5 average rating, 12 reviews

Cozy Lakefront Cottage

Experience the ultimate retreat at our recently remodeled Highland Lake cabin. This small and intimate 2-bedroom home is a nature lover's paradise. Enjoy the outdoor fire pit, perfect for cozy evenings under the stars. Take advantage of our kayaks, paddle boards, and row boat for endless water adventures. Engage in a friendly game of cornhole or enjoy the private dock, ideal for guests bringing their own boat. With great fishing and water activities, our cabin promises unforgettable memories.

Top guest favorite

Cottage in Antrim

4.98 out of 5 average rating, 62 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.

Guest favorite

Cabin in Stoddard

4.83 out of 5 average rating, 131 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

Tiny home in Chesterfield

5 out of 5 average rating, 3 reviews

Cozy Cottage on Spofford Lake

This perfect spot on Spofford Lake will have you coming back every year to make memories without giving up the comfort of home. Plenty of space for everyone inside and out. Comfortably sleeps 4 people. There's so much to enjoy: from a cup of coffee sitting on your porch facing the lake, to swimming, kayaking, paddle-boating, enjoying sunsets while making s-mores for the kids at the campfire, grilling burgers with family and friends, and even streaming your favorite shows on a rainy day.

Guest favorite

Home in Chesterfield

4.96 out of 5 average rating, 52 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 favorite

Chalet in Antrim

4.94 out of 5 average rating, 97 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 favorite

Home in Harrisville

4.9 out of 5 average rating, 10 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 cherished 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!

Guest favorite

Chalet in Stoddard

4.95 out of 5 average rating, 258 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 favorite

Cabin in Stoddard

4.81 out of 5 average rating, 241 reviews

Waterfront Cabin on Beautiful Highland Lake!

Quiet lake experience, especially on weekdays, to get away and reset your busy life! 2 kayaks for your use at no extra charge. We recently added an outdoor shower in addition to 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. You can really unplug with no WIFI! (Pets are not permitted)