Vacation rentals with a kayak in Chesterfield

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Chesterfield

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

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, 217 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.

Top guest favorite

The exterior of a modern house is framed by vibrant autumn foliage, showcasing a blend of orange, yellow, and red leaves. A paved driveway leads to the entrance, accented by stone landscaping and a small garden. Large windows reflect the surrounding nature.

Apartment in Lake Placid

4.98 out of 5 average rating, 187 reviews

VanHoevenberg Ridge upper level apartment.

Magnificent mountain views in the midst of the High Peaks Region and 42.7 acre zoning, six miles from Lake Placid Village's traffic and bustle; this upper level suite features queen master bedroom plus second bedroom with double bed, and Jack and Jill bath, fully equipped kitchen, cathedral dining and living rooms. Relax and enjoy mountain sunsets from hot tub on deck. All-wheel drive needed to manage 1,000-foot paved private drive in winter. North Elba Short Term Rental Permit # STR-200360

Guest favorite

A modern living area is captured with large windows providing natural light and views of the surrounding trees. A gray sectional sofa faces a sleek coffee table, with a brown leather armchair nearby. The streamlined kitchen features a gray countertop and minimalist design elements.

Home in Malletts Bay

4.99 out of 5 average rating, 103 reviews

Modern, hilltop, lakeside retreat!

Escape to a modern summer retreat tucked among the trees on the shores of Lake Champlain’s Mallets Bay. Built in 2021, this serene and stylish hideaway is perfect for peaceful mornings, paddleboarding adventures, and evenings around the Solo Stove. Charge your EV while you watch the sunrise from the dock, sip local coffee with lake views, or explore nearby Burlington and Winooski—just 15 minutes away. Whether you're unwinding on the deck or enjoying the water, this is your perfect summer escape.

Top guest favorite

A serene outdoor space features a patio table surrounded by chairs, set against the calm waters of Metcalf Pond. A large umbrella provides shade, while an American flag gently flutters nearby. The backdrop includes rolling hills adorned with autumn colors.

Cottage in Fletcher

5 out of 5 average rating, 145 reviews

Metcalf Pond Camp Convenient to Smugglers Notch

Handcrafted cozy waterfront camp on Metcalf pond. Propane fireplace provides for welcome warmth after fall or winter adventures. Soak in the Hot tub on the deck. Custom spiral staircase accesses carpeted sleeping loft with books, TV, rocking chair. Enjoy the quiet off season brings to the area when most camps are shuttered for winter. Enjoy staying in and cooking and taking in the cozy atmosphere or make the approximately 20 minute drive to Smugglers Notch or enjoy other local attractions.

Guest favorite

The exterior of the chalet is shown, featuring a spacious wooden deck with several red chairs. Lush greenery and vibrant flowers add color to the scene. Large windows provide views of the surrounding landscape, enhancing the cozy architecture of the home.

Cottage in Keeseville

4.91 out of 5 average rating, 100 reviews

Lakefront Adirondack, private beach❤ +kayaks, Wifi

Our family cottage around Lake Champlain offers the best view you can find in the area! Direct access to the lake with a private beach, a large dock, 2 kayaks and a large garden. The water is crystal clear and the view on the Green Mountains is breath taking. The area is full of nearby things to do: Adirondack Park, Ausable Chasm, White Face Mountain, Lake Placid, Plattsburgh, Burlington, small brewery and winery. The living space is located on the 2nd floor, with a play room on the 1st floor.

Guest favorite

Sunlight filters through tall trees, casting elongated shadows on a grassy area by the lake. The serene water reflects the sky, creating a peaceful atmosphere. A few chairs are positioned on the grass, inviting relaxation and enjoyment of the picturesque surroundings.

Home in Willsboro

4.95 out of 5 average rating, 113 reviews

Quiet 3 Bedroom Cottage on Lake Champlain

You'll have a relaxing visit at this cozy, comfortable family camp. Enjoy swimming, kayaking and hiking. Explore gorgeous Lake Champlain or enjoy the view from the porch. The sunrises are spectacular! Lake Champlain is known for great year-round fishing. Tip: Bring your water shoes for maximum swimming comfort. Hop on the Essex Ferry to Vermont to experience shopping, art, restaurants and museums. The Shelburne Museum and ECHO, Leahy Center for Lake Champlain are perfect for families.

Guest favorite

The spacious mountain lodge is constructed from stone and wood, featuring multiple gabled roofs and large windows. A grassy area surrounds the lodge, and a hammock is visible in the outdoor space, with a clear blue sky providing a serene backdrop.

Home in Au Sable Forks

4.81 out of 5 average rating, 215 reviews

Adirondack Vacation Destination Lodge on Fern Lake

This mountain retreat is designed for relaxation, comfort and fun! Located in the pristine Adirondack Park and located adjacent to Palmer Brook Sportsman Club 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 Jan-Aug months simply include this request in your stay and enjoy the great outdoors all day and relax by the fireplace at night.

Guest favorite

A circular fire pit is surrounded by three rustic wooden benches, positioned on a grassy area among lush trees. Two adults and a child sit comfortably, enjoying the warm glow of the fire. Behind them, the unique treehouse structure, with large windows, blends into the natural setting.

Treehouse in Moretown

4.98 out of 5 average rating, 106 reviews

4-Season Treehouse @ Bliss Ridge; Best Views in VT

thermostat control! LUXURY! 1-of-a-kind, 5⭐️Interior bathroom, @Bliss Ridge - 88acre, OG farm, private estate surrounded by 1000s acre of wilderness. NEW SAUNA& cold plunge!!! Our 2 architectural wonders = real treehouses, built withIN the living trees, not stilted cabins. Equipped w. a fabulous yotel fireplace, indoor hot shower / plumbing, fresh mtn spring water, stable access ramp. Our original Dr. Seuss treehouse, "The Bird’s Nest" is open May-Oct. WiFi avail at the barn! Cell svc works!

Top guest favorite

A log home is illuminated by exterior lights, highlighting its natural wood texture. The path of stone leads to the entrance, framed by manicured grass and logs. Adirondack chairs are positioned on the porch, creating a welcoming outdoor space with a fire pit nearby.

Home in Wilmington

5 out of 5 average rating, 135 reviews

Wilmington Range Log Cabin on the AuSable River

Adirondack log home located on the Ausable River with mountain views of Whiteface Mt and the Wilmington Range. Enjoy the Adirondacks based out of this cute log cabin with rustic charm, views, and peacefulness, located a minute away from Wilmington town center and 5 minutes away from Whiteface Mt Olympic ski area! This 2.5 bedroom charming log chalet-style home is the perfect size for a week or weekend getaway to the Adirondack Mountains. A staircase leads from the home to a riverside deck.

Top guest favorite

A cozy living area features a light-colored sofa adorned with decorative pillows, complemented by a leather armchair. A well-equipped kitchen area showcases green cabinetry, a black refrigerator, and various appliances on the countertop, illuminated by wall-mounted lights. The space maintains a warm atmosphere with wooden accents.

Guest suite in Jericho

5 out of 5 average rating, 112 reviews

Guest Suite w/hot tub & fireplace

Our property in Vermont is a slice of heaven: Set between Burlington & Stowe, 10 minutes off the main highway I-89, with quick access to the main spots in Vermont, but tucked down a dirt road with nothing but the sounds of the stream. On our property we built The Tuckaway Suite, an entirely private guest suite above our garage. With access to a hot tub, and hiking trails right outside the door, this space is a brand new build with cozy cabin vibes. Follow the journey on IG at @VTstays!

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, 343 reviews

Adirondack getaway w/trails, hot tub and sauna

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.

Guest favorite

Two guests are seen enjoying drinks while seated in Adirondack chairs around a fire pit. The modern A-Frame cabin is highlighted in the background, with large windows and an inviting outdoor atmosphere enhanced by warm, ambient lighting.

Cabin in Jay

4.99 out of 5 average rating, 139 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.