
Holiday rentals with a kayak in Cheshire County
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Top-rated Accommodation with a Kayak in Cheshire County
Guests agree: these holiday homes with a 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.
LocationOutdoor spacesHeating

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.
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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!
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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
LocationPetsWalkability

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!
LocationOutdoor spacesAccess

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.
Outdoor spacesLocationCondition

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
Outdoor spacesValueAir conditioning

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.
Outdoor spacesValueBarbecue

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!
ValueOutdoor spacesCheck-in

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!
LocationHospitalityBeach

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!
LocationValueAccess

The Yurt Sanctuary!
Welcome to The Sanctuary! This yurt dwelling experience has been specially curated for you. Nestled on the edge of the woodlands and surrounded by gardens, the yurt has been a special place for our family for over a decade and we are excited to share this sacred space with you. Unplug, relax, and restore while taking refuge in the comfort of our property which has been cultivated by hand since 2005. Tap into the sounds of nature and find solace at The Yurt Sanctuary.
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Popular amenities for Cheshire County kayak rentals
Holiday House Rentals with a Kayak

Lakefront family vacation home
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The Boat House on Granite Lake
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Wake Up on the Water | Private Beach & Dock
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Rustic Charm in Stoddard – Lakeside Escape
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Lake house on walking trail near mountain
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Spacious Highland Lake Retreat: Kayak & Unwind
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The River House
LocationOutdoor spacesHiking

Changes in Attitude
LocationOutdoor spacesBeach
Cottages with a kayak

Cheerful Lakeside Studio Cottage
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Private Lakefront Cottage w/ Boats
Outdoor spacesLocationComfort

Waterfront Cottage on Granite Lake near Keene, NH
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Tiny Cottage on Spofford Lake
Outdoor spacesLocationBarbecue

Cottage on Spofford Lake “Barn”
Outdoor spacesLocationNearby

Cottage on Spofford Lake “Library”
Outdoor spacesLocationHospitality

1890’s Cottage on Spofford Lake, NH
Outdoor spacesDecorFamily

Modern Luxury on the Lake
Outdoor spacesConditionComfort
Cabin rentals with a kayak

Farmhouse Cabin on Spofford Lake
LocationFamilyPets

Beautiful Lakefront Log Cabin
LocationOutdoor spacesSleep quality

2 Cabins & Sauna on Lake Monomonac
FamilyAmenitiesAccuracy

Cabin & Sauna on Lake Monomonac
LocationOutdoor spacesAccuracy

Cabin & Sauna on Lake Monomonac
LocationOutdoor spacesComfort

2 Mi to Boat Ramp: Log Cabin in New Hampshire
Outdoor spacesLocationHospitality

Lakefront Ski Log Cabin on 2 acres
Outdoor spacesLocationHospitality

Stylish 2 BR cabin overlooking your own wilderness
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Destinations to explore
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- 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
- Bear Brook State Park
- Fox Run Golf Club
- Mount Monadnock
- Bromley Mountain Ski Resort
- University of Massachusetts Amherst
- Emerald Lake State Park
- Massachusetts Museum of Contemporary Art
- Smith College
- Mount Sunapee Resort
- Mount Holyoke College
- Palace Theatre
- Camp Plymouth State Park
- The Montague Bookmill
- Quechee Gorge




