Vacation rentals with a kayak in Chesterfield

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Top-rated kayak rentals in Chesterfield

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Guest favorite

Cottage in Fletcher

4.92 out of 5 average rating, 105 reviews

Lakefront Cottage near Smugglers Notch Vermont

SunCroft is the perfect destination for a quiet getaway combined with outdoor activities. This country cottage has gorgeous views of a small lake nestled in mountains. Morning mists coming off the pond’s surface are particularly beautiful while relaxing with coffee and listening to loon calls. Within a few steps of the lake, you can enjoy swimming and kayaking or bring your own fishing poles. The surrounding area offers hiking, biking, and microbreweries. Driving distance to Burlington or Stowe.

Top guest favorite

A modern wooden exterior features a combination of large windows and a welcoming front door. The building includes two spacious garage doors, all set against a backdrop of colorful autumn foliage. A manicured pathway leads to the entrance.

Loft in Keeseville

5 out of 5 average rating, 207 reviews

Adirondack Gem in the Champlain Valley/VT Views

Our country home is nestled in a peaceful wooded area overlooking Lake Champlain and the VT Green Mtns . The 900 sq ft Loft is private and welcoming, with many thoughtful details for your comfort and total relaxation. Cuddle up with comfy chairs, cozy throws and an abundance of books and magazines. It is so quiet, and the beds so comfortable, that a restful night's sleep is almost a guarantee. Kayaking, canoeing, and fishing opportunities abound with water access close-by. Very kid-friendly.

Guest favorite

An aerial view of the mountain lodge is presented, surrounded by vibrant autumn foliage. A serene lake is visible in the background, with distant mountains gently framing the scenic landscape. The expansive green lawn complements the charming exterior of the lodge, creating a sense of tranquility.

Home in Au Sable Forks

4.81 out of 5 average rating, 211 reviews

Adirondack Vacation Destination Lodge on Fern Lake

This mountain retreat is designed for relaxation, comfort and fun! Located in the pristine Adirondack Park the Lodge is located adjacent to The Palmer Brook Sportsman Club Inc. that provides over 5000+ acres of recreational trails for xc skiing (no lifts/ tow rope), snowshoe, snowmobile, atv, mountain bike trails all starting from your doorstep. Arrangements can be made for access simply include this request in your stay and enjoy the great outdoors all day and relax by the fireplace at night.

Guest favorite

A lakeside home is nestled among lush trees on the shore of Lake Iroquois. The structure features a sloped roof and large windows, providing serene views of the water. A small dock is visible, along with kayaks positioned nearby under the green foliage.

Cottage in Hinesburg

4.97 out of 5 average rating, 183 reviews

Gorgeous lakefront home close to Burlington!

Lovely lakeside home w/expansive views of Lake Iroquois! Beautifully furnished 2 bedroom, 1.5 bath home with high-end finishes, hardwood, and slate floors. Relaxing great room, full kitchen, dining room, one-bedroom, and 1/2 bath on the first level. The entire upper level is devoted to a bedroom suite and features its own balcony, an oversized bathroom with a tiled shower, and a soaking tub. 2 kayaks and a canoe are available to explore the lake! 20 min. to Burlington. Pet friendly-fee applies.

Guest favorite

The rustic log cabin features a dark wood exterior with a green shingled roof. A white door framed by flowers is visible, complemented by a small porch. Surrounding the cabin is a grassy area with trees in the background, offering a sense of seclusion.

Cabin in Schroon Lake

4.98 out of 5 average rating, 277 reviews

Quaint Cabin in Schroon

This quaint, rustic, one room log cabin was originally built for overflow family during the summer by my father. The cedar logs were cut from our property giving it a truly authentic Adirondack feel. The cabin sleeps 1-3 people. It's located on a large, beautiful piece of property with two main houses, a barn and garage. You are within walking distance to our private swimming hole and beach. There is a horse arena nearby. This is a great location for many attractions in the Adirondacks.

Guest favorite

A charming treehouse is nestled among lush green trees, featuring large windows that glow warmly at dusk. A connecting bridge is illuminated with string lights, creating a welcoming pathway. Ferns and forest foliage add to the natural surroundings, enhancing the serene woodland atmosphere.

Treehouse in Moretown

4.97 out of 5 average rating, 150 reviews

Treehouse at Bliss Ridge Farm - Best Views in VT!

This treehouse, the Birds Nest, is open May-Oct. Our “4-Season Treehouse @ Bliss Ridge,” is open year-round: https://www.airbnb.com/h/bigtreehouseatblissridgefarm — NEW SAUNA on property! Dr. Seuss-inspired tree home perched @top of 88-acre, organic hill farm, surrounded by 1000s acres of wilderness. Designed by B'fer Roth, DIY network host of The Treehouse Guys - an authentic treehouse built WITHIN living trees, not stilts! Private hiking & panoramic views of Worcester range, MR valley!

Top guest favorite

A forested exterior of a two-story rustic cabin showcases brown wooden siding and a welcoming entrance with a white door. A small deck with railings is situated in front, featuring a cozy seating area, with greenery surrounding the property.

Chalet in Jay

4.9 out of 5 average rating, 336 reviews

Adirondack getaway with private trails an hot tub

My house is tucked in the woods. I'm the last house on my road that is a dead end. With very few neighbors it is a very private location in the heart of the Adirondack mountains. I'm only 20 min from lake placid and Keene and 10 min from whiteface mountain. I'm 10 min lake Everest and and the Ausable. 20 min from mirror lake. Right out the back door there is hiking , skiing, snow shoes trails. There are 2 peaks that can be reached out my front door, Clarke mtn and Hamlin mtn.

Top guest favorite

The cabin is surrounded by trees, featuring a spacious deck with glowing lights. A hot tub is visible adjacent to the exterior. A fire pit area is arranged with seating, surrounded by a well-maintained lawn, creating a welcoming outdoor space.

Cabin in Jay

4.99 out of 5 average rating, 126 reviews

Modern Hot Tub Sauna A-Frame near Whiteface

Welcome to the Black Pine Lodge! Nestled in the heart of the Adirondacks, this modern A-Frame 3 bed/3 bath cabin can accommodate up to 8 guests. Amenities: Hot Tub Panoramic Barrel Sauna Pool Table Helix mattresses Fire Pit Kayaks Surrounded by beautiful trees this place feels tranquil and has lots of hiking trails outside the front door. Explore other hikes, rivers & dining in neighboring Wilmington, Keene and Lake Placid. End the day relaxing at this lodge that caters to all.

Top guest favorite

An aerial view of a cozy library reveals tall bookshelves filled with various books. A small round table sits in front of a stained glass window, accompanied by a comfortable couch and an ornate rug. Wooden accents add warmth to the space.

Cabin in Loon Lake

4.99 out of 5 average rating, 205 reviews

The Library at Camp Arden

Do you love books enough to sleep with them? Step into the Library at Camp Arden, furnished with one-of-a-kind antiques and collectibles. Curl up with your favorite book and take in the light of antique stained glass and the sounds of the Adirondacks gently wafting through the window. Take a paddle on Carpenter Pond with a provided canoe, or snuggle by the fire outside your door by your own fire-pit. No matter what you do, Camp Arden is waiting to help you enjoy the Adirondacks.

Guest favorite

A spacious house is set on a grassy lawn, surrounded by trees. The structure features multiple windows that allow natural light, a welcoming front porch, and a driveway leading to an outbuilding. The clear sky enhances the serene outdoor environment.

Villa in Schuyler Falls

4.98 out of 5 average rating, 104 reviews

Adirondack Home

The Adirondack home is a cozy warm house, sitting on a 45 acres property in Schuyler Falls, NY with gorgeous surrounding nature located between lake champlain and whiteface moutain. If you’re looking to enjoy a nice sauna, a warm jacuzzi, and/or a relaxing night with fire on a clear sky, don’t hesitate to book. It is a haven for a couple romantic getaway, a skiing experience, or a relaxing family time in the Adirondack nature. Parties are not allowed for safety reasons.

Top guest favorite

An aerial view captures a charming barn-style home surrounded by lush greenery, with expansive views of a serene lake in the background. The property features meticulously maintained lawns and a landscape rich in trees, set against a backdrop of rolling hills and distant mountains.

Barn in Hinesburg

4.99 out of 5 average rating, 137 reviews

Cozy Cabin -Top of Hill with Views

Experience the ultimate Vermont retreat in our newly renovated second-story guest space nestled in a charming barn, offering breathtaking easterly views of the Green Mountain range, including the majestic Camels Hump and Bolton peaks. This hilltop cabin is cocooned by lush trees and verdant pastures, providing an idyllic escape from the hustle and bustle of everyday life. Kayak, swim or paddleboard on nearby Lake Iroquois 2 miles away or Lake Champlain 9 miles away.

Guest favorite

A covered porch features rustic wooden flooring and multiple Adirondack chairs arranged for relaxation. The open space offers expansive views of the farm, open fields, and distant landscapes, including Lake Champlain and surrounding mountains.

Cottage in Moriah

4.98 out of 5 average rating, 161 reviews

Pearl of the Mountain

The Beebe Farm was started in 1921 by Fred and Pearl Beebe. There are now four generations of Beebe's who have farmed this land. Over time these spectacular views have been created by hard work and devotion to agriculture. We offer this rental for you to relax and enjoy the breathtaking panorama of Lake Champlain, the Green Mountains of Vermont, and the eastern slopes of the Adirondacks. Many activities and attractions can be found close by!