
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.
ValueOutdoor spacesFamily

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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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
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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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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!
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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.
LocationOutdoor spacesAmenities

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
ValueLocationCleanliness

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.
LocationValueDecor

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!
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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!
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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!
LocationOutdoor spacesCheckout

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.
LocationOutdoor spacesQuiet
Popular amenities for Cheshire County kayak rentals
Holiday House Rentals with a Kayak

The River House
ValueLocationRiver

Wake Up on the Water | Private Beach & Dock
Outdoor spacesLocationAir conditioning

Lakehouse Getaway
LocationOutdoor spacesView

The Boat House on Granite Lake
ValueLocationHospitality

Rustic Charm in Stoddard – Lakeside Escape
Outdoor spacesValueCheck-in

The Shoreline
Outdoor spacesLocationSleep quality

Changes in Attitude
Outdoor spacesLocationAccess

Divol Pond Cabin
LocationOutdoor spacesAccuracy
Cottages with a kayak

Modern Quiet Lakeside Retreat
ValueOutdoor spacesPets

Lakefront Escape•HOT TUB•Fishing •Swimming•Boats
Outdoor spacesLocationCheck-in

3 bedroom home. Swimming out your back door
Outdoor spacesLocationKitchen

Waterfront Cottage on Granite Lake near Keene, NH
Outdoor spacesValueBackyard

Tiny Cottage on Spofford Lake
LocationOutdoor spacesHospitality

The Monadnock Manse
Outdoor spacesBathroomHospitality

Modern Luxury on the Lake
Outdoor spacesIndoor spacesAmenities

Private Lakefront Cottage w/ Boats
LocationOutdoor spacesBackyard
Cabin rentals with a kayak

The Birches Cabin, at home in the woods!
Outdoor spacesLocationBiking

Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Outdoor spacesValueHiking

Beautiful Lakefront Log Cabin
Outdoor spacesLocationIndoor spaces

Waterfront Cabin on Beautiful Highland Lake!
Outdoor spacesLocationLayout

Cozy Comfort on 250 Acre Private Estate
Outdoor spacesLocationPets

Stylish 2 BR cabin overlooking your own wilderness
Outdoor spacesLocationWi-Fi

Cabin & Sauna on Lake Monomonac
LocationOutdoor spacesQuiet

Lakefront Ski Log Cabin on 2 acres
Outdoor spacesLocationHospitality
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




