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

Home in Washington

5 out of 5 average rating, 98 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 favorite

Cabin in Washington

4.93 out of 5 average rating, 15 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 favorite

Home in Rindge

5 out of 5 average rating, 33 reviews

Lake house on walking trail near mountain

You will feel your worries melt away as you travel down the dirt road onto the rail trail to this newly rebuilt home with water views on 3 sides. Your family will make memories for a lifetime in this quiet, spacious, open floor plan, 5-bedroom home. Enjoy creating meals together in the chef's kitchen. The house offers an easy, casual flow and encourages guest to reconnect and spend time together in any of the large shared spaces. Check the list of bedrooms to make sure they meet your needs.

Guest favorite

Cabin in Rindge

4.98 out of 5 average rating, 121 reviews

Lakeside 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 just a short 2-min walk to a private beach on Lake Contoocook! Vacation on 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.

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 Stoddard

4.95 out of 5 average rating, 236 reviews

Highland Haus-70s AFrame-short walk to lake/canoe

Cozy 1975 A-frame chalet cabin sleeps 5 with a comfortable living space, two wood stoves, and a full kitchen. Located in the rural community of Stoddard. Enjoy the peace and quiet that this area has to offer. Many local hiking, swimming and fishing nearby. In warmer months, guests will have access to our canoe. It is less than a 2-hour drive from Boston to the Highland Haus! Winter Guests- please note that Shedd Hill rd is very hilly and all-wheel drive or 4-wheel drive is recommended.

Guest favorite

Home in Washington

5 out of 5 average rating, 19 reviews

Thanksgiving Retreat, Hot Tub & Cozy Fire Pit

Embrace the Fall & Winter Magic at Our Cozy Family Retreat! Nestled on a peaceful road, our home invites families for an unforgettable getaway. Explore the beauty of the changing leaves or enjoy winter activities nearby. Unwind in our inviting hot tub after a day of adventure and chill. Relax on our two decks or make s’mores at the outdoor fire pit, perfect for cozy gatherings under the stars. Secure your winter escape now for an unforgettable journey into seasonal delights.

Guest favorite

Chalet in Antrim

4.94 out of 5 average rating, 78 reviews

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

Our year-round A-Frame cabin is 30 min to Mount Sunapee, 20 min to Crotched, and 15 min to Pat's Peak! We are on a small 32-acre pond in New Hampshire. It is truly heaven on earth. We have 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

Cottage in Winchendon

4.97 out of 5 average rating, 34 reviews

Top 10 of VRBO -Copley's Lakefront Cottage on Lake

A very unique, beautifully designed Belgium Farm House on Lake Monomonac, who's waters straddle both Massachusetts and New Hampshire. Your own sandy beach and dock to enjoy everything the lake has to offer. All seasons can be thoroughly enjoyed here; boating, fishing, swimming and other water sports in the summer, vibrant colors and crisp air of fall, in the winter enjoy iceskating and fishing, then end the day with a good book by the fireplace.

Guest favorite

Home in Rindge

4.95 out of 5 average rating, 21 reviews

The Shoreline

Welcome to The Shoreline. This Classic New England Lakehouse is located on Lake Monomonac, minutes away from amenities but tucked away in small town America. This property is the ideal getaway for a relaxing vacation. The kitchen and living areas are comfortable and clean, but the real star is the lake itself—perfect for boating, kayaking, swimming, and fishing. Enjoy the 180 degree water views and over 500 ft of beautiful shoreline.

Guest favorite

Cabin in Rindge

5 out of 5 average rating, 13 reviews

Finnish Cottage + Sauna on Lake Monomonac

Authentic Finnish Cottage with Sauna on Lake Monomonac with private dock and boat ramp for your boat, jet ski, or sailboat. Includes canoes, kayaks, bikes, tennis court, basketball court, baseball field. Great area for hiking, biking, snow skiing and snowmobiling. Close to Mt Monadnock, Mt Watatik , Mt. Wachusett, Pats Peak, Granite Gorge Mountain Peak, and Crotched Mountain. 1 hour and 30 minutes from Boston, 4 hours from NY.

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)