Holiday rentals with a kayak in Cheshire County

4.98 out of 5 average rating, 114 reviews

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.

5 out of 5 average rating, 117 reviews

Home in Washington

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.

5 out of 5 average rating, 38 reviews

Cabin in Rindge

Red Cabin & Sauna on Lake Monomonac

Authentic Finnish Cottage with Sauna on Lake Monomonac. Includes canoes, kayaks, bikes, private boat launch, and a private dock for your boat, jet ski, or sailboat. Also has tennis courts, basketball court, baseball and soccer field. Great area for hiking, biking, snow skiing and snowmobiling. Close to Mt Monadnock, Mt. Wachusett Pats Peak, Granite Gorge Mountain Peak, and Crotched Mountain. 1 hour and 45 minutes from Boston airport, 50 minutes from Manchester airport and 4 hours from NYC.

4.84 out of 5 average rating, 138 reviews

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!

Superhost

Home in Chesterfield

4.9 out of 5 average rating, 123 reviews

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.

5 out of 5 average rating, 16 reviews

Home in Nelson

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!

4.95 out of 5 average rating, 65 reviews

Home in Chesterfield

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 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 1/4 mile away. 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.

4.92 out of 5 average rating, 25 reviews

GiGi's Cabin/ 314' Shoreline

Uncover a tranquil lakeside haven for family and friends. Enjoy the distinctive charm of the main cabin and cozy bunkhouse. Embrace breathtaking lake views from the property, accentuated by the 314' of private shoreline and excellent fishing at the nearby dock. For outdoor enthusiasts, explore surrounding trails for endless hiking and biking adventures. A complimentary kayak awaits for serene water exploration, while the expansive dock beckons boats. Immerse yourself in nature's beauty.

Superhost

Chalet in Antrim

4.91 out of 5 average rating, 113 reviews

Direct Waterfront A-Frame, Close to 3 Ski Areas!

My year-round A-Frame cabin is 30 min to Mount Sunapee, 20 min to Crotched, and 15 min to Pat's Peak! It’s on a small 32-acre pond in New Hampshire. It is truly heaven on earth. There is over 100 feet of direct waterfront. There is a 6 foot main dock, and a small fishing dock off to the side. The fishing on our pond gets rave reviews! Most people catch and release, but please follow NH fishing laws: 16+ needs a license. The property sits on 1/3 of an acre, on a sloped hill.

4.95 out of 5 average rating, 279 reviews

Chalet in Stoddard

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!

4.94 out of 5 average rating, 18 reviews

Home in Harrisville

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!