
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.
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The River House
Take it easy at this unique and tranquil getaway on the Connecticut River. Large 2-tier deck with steps to private boat dock Jun 15-Oct 15 right on the river. Wake up to amazing views of the river with the stillness of nature around you. Superb water skiing with 18 miles of wide, deep river. Excellent fishing. A habitat for bald eagles. Boat launch nearby. Under 1 hr to major ski areas including Okemo, Mount Snow, Stratton and Magic Mountain. 15 min to Brattleboro Ski Hill. Granite Gorge 30 min.
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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
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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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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
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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.
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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!
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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!
LocationOutdoor spacesHospitality

Lakefront Mid-Century Cottage with Sandy Beach
Welcome to Hudson's Hideaway- a peaceful lakeside retreat where simple charm meets unforgettable views. Tucked among the pine trees at the end of a quiet, bumpy dirt road, this classic 1940's three season cottage is the kind of place that lets you slow down and reconnect with nature. While the cottage proudly shows its vintage character, it has been lovingly maintained and thoughtfully stocked with everything you need for a comfortable stay. The real star is the location.
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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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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 Crowcroft House
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Modern Lakefront Home
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Changes in Attitude
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Cottages with a kayak

Cheerful Lakeside Studio Cottage
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Private Lakefront Cottage w/ Boats
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Waterfront Cottage on Granite Lake near Keene, NH
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Tiny Cottage on Spofford Lake
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Cottage on Spofford Lake “Barn”
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Cottage on Spofford Lake “Library”
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1890’s Cottage on Spofford Lake, NH
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Modern Luxury on the Lake
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Cabin rentals with a kayak

Farmhouse Cabin on Spofford Lake
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Beautiful Lakefront Log Cabin
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Highland Lake Waterfront Cabin
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Cabin & Sauna on Lake Monomonac
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Cabin & Sauna on Lake Monomonac
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GiGi's Cabin/ 314' Shoreline
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Lakefront Ski Log Cabin on 2 acres
Outdoor spacesLocationHiking

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
- Quechee Gorge
- The Montague Bookmill




