
Vacation rentals with a kayak in Cheshire County
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Top-rated kayak rentals in Cheshire County
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Cozy Comfort on 250 Acre Private Estate
If you’re looking for serenity, peace and quiet, you've found it, amidst a 250 acre private estate. On a lake at the end of a mile long driveway (well plowed in the winter) Is Snowshoe Cabin. Built in 1929 as the garage for "Lakefalls Lodge, it's been completed renovated into a luxurious, cozy home with modern amenities. Guests rave about "views of the snowy pond while you’re warm inside" from heated floors and a wood burning stove with free firewood. Spikes provided for wonderful winter walks.

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.

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!

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

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!

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.

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

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.

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!

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!

Highland Lake Waterfront Cabin
Escape to our picturesque waterfront A-Frame vacation home, nestled on the serene Highland Lake in NH. With a private dock, provided kayaks and paddle board, indulge in exhilarating water sports or cast a line for a memorable fishing adventure. Boasting 3 cozy bedrooms, accommodating up to 6 guests, our retreat is the perfect blend of comfort and tranquility. Just a short 2 hr drive from Boston, immerse yourself in nature's embrace. Book now for an idyllic lakeside getaway!

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!
Popular amenities for Cheshire County kayak rentals
House rentals with a kayak

Lakefront family vacation home

Wake Up on the Water | Private Beach & Dock

The Cozy Place

Amazing Lakefront Home with Pool- Tatum's Place

Lake house on walking trail near mountain

Spacious Highland Lake Retreat: Kayak & Unwind

The River House

Changes in Attitude
Cottage rentals with a kayak

Cheerful Lakeside Studio Cottage

Private Lakefront Cottage w/ Boats

Waterfront Cottage on Granite Lake near Keene, NH

Tiny Cottage on Spofford Lake

Cottage on Spofford Lake “Barn”

Cottage on Spofford Lake “Library”

Modern Luxury on the Lake

Blacksmith Cottage on Spofford Lake
Cabin rentals with a kayak

Farmhouse Cabin on Spofford Lake

Beautiful Lakefront Log Cabin

Cabin & Sauna on Lake Monomonac

Cabin & Sauna on Lake Monomonac

Boulder House - Extraordinary Luxury in the Woods!

1890’s Cabin on Spofford Lake, NH

GiGi's Cabin/ 314' Shoreline

Lakefront Ski Log Cabin on 2 acres
Destinations to explore
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- Rentals with a washer and dryer Cheshire County
- Beachfront rentals Cheshire County
- Pet-friendly rentals Cheshire County
- Rentals with lake access Cheshire County
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- Tiny house rentals Cheshire County
- Waterfront rentals Cheshire County
- Rentals with a kayak New Hampshire
- Rentals with a kayak United States
- Okemo Mountain Resort
- Stratton Mountain
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Monadnock State Park
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Snhu Arena
- Ragged Mountain Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Bear Brook State Park
- Bromley Mountain Ski Resort
- University of Massachusetts Amherst
- Mount Sunapee Resort
- Mount Monadnock
- Smith College
- Emerald Lake State Park
- Massachusetts Museum of Contemporary Art
- Mount Holyoke College
- Palace Theatre
- Camp Plymouth State Park
- The Montague Bookmill
- Quechee Gorge





