
Holiday rentals with a kayak in Cheshire County
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Top-rated rentals with kayak in Cheshire County
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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.

Lakefront Escape•HOT TUB•Fishing •Swimming•Boats
Relax with the whole family at our Pearly lake cottage! Home is very clean, warm and cozy! Bedroom on the first floor has a queen bed and a crib. Second bedroom upstairs, offers two queen beds and has an AC in the bedrooms. The bonus room has two smaller bunk beds. Living room has a pull out couch. Kitchen is fully equipped. The place offers a grill, fireplace, two kayaks, canoe and a boat for your enjoyment! Monadnock State Park is only 15 min away with multiple hiking trails and great views

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!

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.

Picturesque 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 in the beautiful Monadnock region by Lake Contoocook! Vacation near 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.

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

Lakefront family vacation home

The Boat House on Granite Lake

Wake Up on the Water | Private Beach & Dock

Rustic Charm in Stoddard – Lakeside Escape

Spacious Highland Lake Retreat: Kayak & Unwind

Modern Lakefront Home

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

2 Cabins & Sauna on Lake Monomonac

Cabin & Sauna on Lake Monomonac

Cabin & Sauna on Lake Monomonac

1890’s Cabin on Spofford Lake, NH

Lakefront Ski Log Cabin on 2 acres

Stylish 2 BR cabin overlooking your own wilderness
Destinations to explore
- Rentals with a firepit Cheshire County
- Flat rentals Cheshire County
- Rentals with a hot tub Cheshire County
- Rentals with outdoor seating Cheshire County
- House rentals Cheshire County
- Family-friendly rentals Cheshire County
- Farm stay rentals Cheshire County
- Rentals with a washing machine and dryer Cheshire County
- Beachfront rentals Cheshire County
- Pet-friendly rentals Cheshire County
- Rentals with lake access Cheshire County
- Guest house rentals Cheshire County
- Private suite rentals Cheshire County
- Rentals with pools Cheshire County
- Rentals with a fireplace Cheshire County
- Rentals with a patio Cheshire County
- Rentals with breakfast Cheshire County
- 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
- Mount Monadnock
- University of Massachusetts Amherst
- Mount Sunapee Resort
- Emerald Lake State Park
- Smith College
- Massachusetts Museum of Contemporary Art
- Palace Theatre
- Mount Holyoke College
- Camp Plymouth State Park
- The Montague Bookmill
- Quechee Gorge




