
Holiday rentals with a kayak in Cheshire County
Find and book unique kayak rentals on Airbnb
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.

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!

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.

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.

Cabin & Sauna on Lake Monomonac
Beautiful Finnish House and a Sauna on Lake Monomonac. 2 bedrooms, sleeps 4+ people comfortably with a full kitchen and bathroom and outdoor shower. Dock and boat launch/ramp including canoes, kayaks and sports equipment. Beautiful clean lake for boating, fishing, skiing and swimming. Close to Mt Monadnock (2nd most hiked mountain in the world), Mt. Wachusett Pats Peak, Granite Gorge Mountain Peak, and Crotched Mountain for hiking and skiing. 1 hr from Boston airport and 4 hrs from NYC.

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!

Divol Pond Cabin
Family friendly rustic style interior home tucked away on a private dead end road. Small private pond with only three houses with access. Stunning deck with waterview connected to master bedroom with cathedral ceiling and skylights. Small fire pit. Grill. Dual heat propane fire pit table. Dock, kayak, paddle boat, hammock. Mount Watatic five minutes away. Mount Monadnock 20 minutes away. Restaurants, grocery stores/shopping close by. Perfect place to relax and enjoy quite times of nature.

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!

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!

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

Lakefront family vacation home

Waterfront Paradise

Magic Lakehouse, Waterfront, Private Beach & Dock

The Cozy Place

Amazing Lakefront Home with Pool- Tatum's Place

Winter Ski Getaway with Hot Tub & Fire Pit

Family Friendly Lakefront Home

The River House
Cottage rentals with a kayak

Cheerful Lakeside Studio Cottage

Waterfront Cottage on Granite Lake near Keene, NH

Tiny Cottage on Spofford Lake

Cottage on Spofford Lake “Barn”

Cottage on Spofford Lake “Library”

Blacksmith Cottage on Spofford Lake

3 bedroom home. Swimming out your back door

The Monadnock Manse
Cabin rentals with a kayak

Farmhouse Cabin on Spofford Lake

Beautiful Lakefront Log Cabin

Highland Lake Waterfront Cabin

Cabin & Sauna on Lake Monomonac

Cabin & Sauna on Lake Monomonac

Picturesque Log Cabin near Mt Monadnock

2 Mi to Boat Ramp: Log Cabin in New Hampshire

GiGi's Cabin/ 314' Shoreline
Destinations to explore
- Rentals with a hot tub Cheshire County
- Cabin rentals Cheshire County
- Rentals with outdoor seating Cheshire County
- House rentals Cheshire County
- Rentals with a washing machine and dryer Cheshire County
- Rentals with a firepit Cheshire County
- Tiny house rentals Cheshire County
- Waterfront rentals Cheshire County
- Rentals with lake access Cheshire County
- Pet-friendly rentals Cheshire County
- Family-friendly rentals Cheshire County
- Guest house rentals Cheshire County
- Flat rentals Cheshire County
- Beachfront rentals Cheshire County
- Rentals with pools Cheshire County
- Rentals with a patio Cheshire County
- Rentals with a fireplace Cheshire County
- Private suite rentals Cheshire County
- Farm stay rentals Cheshire County
- Rentals with a kayak New Hampshire
- Rentals with a kayak United States
- Okemo Mountain Resort
- Stratton Mountain
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Monadnock State Park
- Stratton Mountain Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Bear Brook State Park
- Fox Run Golf Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Snhu Arena
- Mount Sunapee Resort
- Emerald Lake State Park
- Smith College
- Mount Holyoke College
- Southern Vermont Arts Center
- Massachusetts Museum of Contemporary Art
- Mount Monadnock
- University of Massachusetts Amherst
- Magic Wings Butterfly Conservatory and Gardens
- Look Memorial Park




