
Holiday rentals with a kayak in Chesterfield
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Chesterfield
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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.

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.

Modern, hilltop, lakeside retreat!
Escape to a modern winter retreat nestled among towering trees with stunning views of Mallets Bay. This cozy, luxurious haven, built in 2021, is perfect for gathering with loved ones or a peaceful getaway. Just 15 minutes from Burlington and Winooski, enjoy nearby dining, unique shops & winter adventures. End your day around the Solo Stove for a cozy fire, sharing stories and laughter under the stars. Start each morning with lake views & local coffee—our serene space is the ideal winter escape!

Rockhaven - Island View
Rockhaven, a romantic getaway is a rare find. Step back in time and enjoy almost 600' of lake shore on Vermont's unique Lake Champlain with 180 degree views, from westerly views to New York's Adirondacks, through the north and east to Vermont's Green Mountains. This private site is 2 acres with mature trees, meadows, and wooded buffers, ensuring a peaceful and private stay. There are two cottages available; they can be rented separately or together. Each is one bedroom with private bath.

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.

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 - built WITHIN living trees, not stilts! Private hiking & panoramic views of Worcester range, MR valley! No pets or animals please.

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.

Luxury ADK Retreat Near Whiteface, Lake Placid
ADIRONDACK MOUNTAIN CABIN – Your luxury Adirondack escape! This 3-bedroom, 2-bath retreat sleeps 8 guests and is 17 minutes to Whiteface, a half hour to Lake Placid, and steps from Lake Eaton and scenic trails. Relax in the private hot tub, gather around the fire pit, or enjoy the 3-season sunroom, covered deck, and game room, featuring foosball and Smart TV. A stunning floor-to-ceiling stone gas fireplace and modern Adirondack décor make this the perfect 4-season getaway. Dog friendly!

Heron Pointe @ Silver Lake near Whiteface Mtns
Heron Pointe Camp is located near Whiteface Mountain and Lake Placid in the Adirondack Park. A beautiful lakefront location on Silver Lake. Near Saranac Lake. Private dock & kayaks. Perfect for a couple, small family or professionals. Close to many Adirondack peaks, lakes, rivers, ponds, hiking trails and skiing. Silver lake is a private lake approximately 3.5 miles long end to end with perimeter shoreline of 13+miles. Nice for swimming, fishing, paddling and relaxing lakeside.

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.

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.

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!
Popular amenities for kayak rentals in Chesterfield
House rentals with a kayak

Spacious Lakefront Retreat w/Stunning Views

Tranquil lake house in VT w/ breathtaking views

Comfy 3 bedroom home tucked away on the bay

Waterfront, Hot tub, Pet friendly, 5min-White face

Nature Lover's Paradise

Lake Champlain Retreat & Sauna

Lake Champlain Colonial

Private lakefront oasis
Cottage rentals with a kayak

Lakefront Home, Large yard, w/Dock, sleeps 10+

Summer home with private lake front

Bluebird Cottage on Lake Champlain

Lake front home on private, tree-lined drive.

Historic Tucker Cottage on Lake Champlain

Camel's Hump Remote Mountain Cottage

Gorgeous lakefront home close to Burlington!

Cozy cottage at “The 588 By The Lake”
Cabin rentals with a kayak

Privacy and serenity. Just hit "reserve"!

Quaint Cabin in Schroon

ZaLo House Waterline cabin with Hot Tub Pets

Water's Edge Log Cabin

Lake Iroquois - "Lakes End"

Maplewood Cabin, hideaway w/ hot tub + fireplace

Willsboro Point Waterfront Retreat

Cabin With a Giant View
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Pocono Mountains Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Family-friendly rentals Chesterfield
- Rentals with a fireplace Chesterfield
- Rentals with a patio Chesterfield
- Rentals with a firepit Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Rentals with beach access Chesterfield
- Pet-friendly rentals Chesterfield
- Waterfront rentals Chesterfield
- Rentals with outdoor seating Chesterfield
- House rentals Chesterfield
- Rentals with lake access Chesterfield
- Rentals with a kayak Essex County
- Rentals with a kayak New York
- Rentals with a kayak United States
- Sugarbush Resort
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Lake Flower
- Stowe Mountain Resort
- Middlebury College
- University of Vermont
- ECHO, Leahy Center for Lake Champlain
- Adirondak Loj
- Shelburne Museum
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- Warren Falls
- Shelburne Vineyard
- Snow Farm Vineyard & Winery
- Waterfront Park
- Elmore State Park
- Cold Hollow Cider Mill





