Vacation rentals with a kayak in Cheshire County

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Top-rated kayak rentals in Cheshire County

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Guest favorite

Chalet in Winchester

4.87 out of 5 average rating, 61 reviews

Chalet Sonsie: A Sweetwater Stay

Chalet Sonsie is a freshly-renovated waterfront getaway, where you can enjoy breathtaking views of Forest Lake year-round, from every room and all 3 levels of decks! Whether you're traveling with the kids, friends, or just looking for a quiet fishing retreat, there's something here for everyone. This cozy 2-bedroom home features 2 full kitchens, 1.5 baths, expansive fireplace and TV, plus a game room complete with foosball and mini-arcade! Book today, or check out other Sweetwater Stays! -Patti

Mar 24 – 31

G$29,803 GYD per night

Guest favorite

Tent in Chesterfield

5.0 out of 5 average rating, 28 reviews

The Ultimate Romantic Glamping Getaway

Fall asleep to the sounds of nature in this gorgeous, 200 square foot, smoke-free glamping tent in Chesterfield, NH. Located just 1.5 miles from beautiful Spofford Lake in southwestern NH, perfect for boating and fishing. Five miles from the Connecticut River and Vermont. Close to bike trails and hiking. Your glamping get-away includes the use of garden areas, bistro tables at the lighted pergola, a cozy screen house and fire pit. Free coffee or tea are served each morning. Your retreat awaits.

Aug 22 – 29

G$33,721 GYD per night

Guest favorite

Cabin in Marlow

4.97 out of 5 average rating, 110 reviews

The Birches Cabin, at home in the woods!

The Birches is situated on 10 secluded acres, where guests will enjoy the privacy and scenery the cabin offers. Built in 2020 and designed to accommodate guests. During your stay take a walk on the property, read a book, enjoy a glass a wine, cook a fine meal, and stare at the stars. Centrally between Keene and the Sunapee region, guests have many options on how to enjoy their days such as Skiing, Hiking, Paddling, and Snow tubing. This is a vacation spot, that can be enjoyed all year.

Apr 7 – 14

G$25,802 GYD per night

Guest favorite

Farm stay in Stoddard

5.0 out of 5 average rating, 77 reviews

Upton Farm and Forest

Upton Farm & Forest is a beautiful, unique, peaceful setting on 200 acres in SW New Hampshire. Once a farm from the 1800s now there is my off-grid, solar powered, timber framed home (you'll be staying in the addition), 6 acres of meadow, 3+ miles of trails, 10 acre beaver pond and the original Upton farmhouse. Wildlife abounds and mountain views. Look at photos in slideshow mode (click on photos and click again for slideshow.) The captions will describe the house, amenities, and surroundings.

Sep 14 – 21

G$35,769 GYD per night

Superhost

Cabin in Stoddard

4.82 out of 5 average rating, 111 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!

Sep 16 – 23

G$27,082 GYD per night

Guest favorite

Cabin in Rindge

4.99 out of 5 average rating, 106 reviews

Lakeside Log Cabin near Mt Monadnock

Welcome to Cabin at the Cove! This spacious 4-bedroom 2-bathroom log cabin sleeps 10 + up to 2 dogs. The cabin offers rustic charm with modern amenities and is located just a short 2-min walk to a private beach on Lake Contoocook! Vacation on a picturesque lake, hike to leaf peep from the top of beautiful Mount Monadnock, cross-country ski, or curl up with a book by the fire – there is something for everyone year-round. While only 90 minutes from Boston, it feels like a true nature escape.

Jul 10 – 17

G$144,273 GYD per night

Guest favorite

Home in Chesterfield

4.95 out of 5 average rating, 41 reviews

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.

Sep 19 – 26

G$37,258 GYD per night

Guest favorite

Chalet in Stoddard

4.95 out of 5 average rating, 195 reviews

Highland Haus- Cozy 70s AFrame- two wood stoves

Cozy 1975 A-frame chalet cabin sleeps 4 with a comfortable living space, two wood stoves, and a full kitchen. Located in the rural community of Stoddard. Enjoy the peace and quiet that this area has to offer. Many local hiking, swimming and fishing nearby. It is less than a 2-hour drive from Boston to the Highland Haus! Winter Guests- please note that Shedd Hill rd is very hilly and can be difficult to drive after a fresh snowstorm, all-wheel drive or 4-wheel drive is recommended.

Jul 11 – 18

G$33,876 GYD per night

Superhost

Cabin in Stoddard

4.8 out of 5 average rating, 218 reviews

Waterfront Cabin on Beautiful Highland Lake!

Quiet lake experience, especially on weekdays, to get away and reset your busy life! 2 kayaks for your use at no extra charge. We recently added an outdoor shower in addition to an indoor claw foot bath tub. There is a small private outdoor deck. Lots to do in the surrounding area, but most people don't want to leave this beautiful setting. You can really unplug with no WIFI! (Pets are not permitted)

Oct 6 – 13

G$31,500 GYD per night

Guest favorite

Cottage in Jaffrey

5.0 out of 5 average rating, 17 reviews

The Boathouse - A rustic and cozy lakeside cottage

Take it easy at this tranquil lakeside getaway. Enjoy over 100 feet of waterfront at the foothills of Mt. Monadnock. Rustic cottage on 1 acre of woods off a dirt road. 200 square feet of new composite dock with 2 kayaks and paddle boards. Outdoor fireplace, picnic table and hammock trees provide for the ultimate in adventure and relaxation.

Feb 8 – 15

G$60,551 GYD per night

Guest favorite

Home in Alstead

5.0 out of 5 average rating, 19 reviews

The Lake House

Relax with friends or family at this peaceful place to stay. Outfitted with two porches, space for four guests, and plenty of privacy. A beautiful spot, ideal for a vacation on the lake. Swim, kayak, explore the island, or just relax on the porch with your favorite drink. You will find this quiet get-a-way home has everything you need.

Dec 3 – 10

G$48,288 GYD per night

Guest favorite

Cabin in Stoddard

4.98 out of 5 average rating, 160 reviews

Cozy Comfort on 250 Acre Private Estate

If you’re looking for serenity, peace and quiet, you've found it situated on a private lake at the end of a mile long driveway amidst a 250 acre estate. Built in 1929 as the garage for "Lakefalls Lodge", Snowshoe Cabin was completely renovated and expanded in 2006 into a luxurious and cozy home with modern amenities.

Dec 2 – 9

G$50,180 GYD per night