
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.

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.

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

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!

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.

Lake Iroquois - "Lakes End"
Lakes End on Lake Iroquois in Hinesburg VT. Gorgeous views of the lake from the deck. Located 50 feet from shore with steps leading to water. Cute kitchen with fridge, oven, refrigerator. Counter space for meals. Large living room. Master bedroom with queen bed, bunks beds. Deck & Grill 40 ft of lake frontage, private dock. Paddle kayaks, hike trails from property. The road is plowed and relatively flat. In winter you need at least all season but preferably snow tires to access.

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!

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.

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.

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.

Lakeside getaway on Lake Champlain
Welcome to our cottage located on a sandy beach just steps from Lake Champlain. With a private entrance, this is the perfect retreat for couples or solo travelers. The cottage is fully equipped with everything you need with well-appointed kitchen & a King size bed. You'll also have access to high-speed internet & a smart TV. Situated just off the causeway bike path, you'll have access to miles of biking and walking trails. Downtown Burlington is just a 15-minute drive away.

A-Frame Adirondack Chalet w/ Lake Access & Trails
Pet & family friendly high-tech mountain escape by lake, trails and mountains Amenities include: high speed internet/WiFi Roku TV Dedicated work space large deck overlooking wooded acres fenced-in rear yard perfect for dogs full kitchen w/ cookware washer & dryer air conditioning supplemental wood-burning stove (inside) Fire pit (outside) 10 miles of private community hiking/skiing trails & lake for kayaking & fishing community playground, tennis courts, grill/picnic area.

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.
Popular amenities for Chesterfield kayak rentals
House rentals with a kayak

Spacious Lakefront Retreat w/Stunning Views

Adirondack A-frame 4bd-2ba: Ski/Hike/Bike & More

Lake Dunmore Getaway — Foliage Views & Ski Retreat

Tranquil lake house in VT w/ breathtaking views

Birchwood Lodge - Our Home in the Woods

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

Spectacular views at the “Edge” of Lake Champlain

Atlas (2025-STR-0303)
Cottage rentals with a kayak

Bluebird Cottage on Lake Champlain

Metcalf Pond Camp Convenient to Smugglers Notch

Lakefront Cottage near Smugglers Notch Vermont

Waterfront Kayak and relax on Great Chazy River

Keeler Bay Lakefront 1BR Cottage (Otter Creek)

Camel's Hump Remote Mountain Cottage

Pearl of the Mountain

Storybook Cottage in the Champlain Islands
Cabin rentals with a kayak

Cairn Cabin: Free children's book! Fall foliage!

Quaint Cabin in Schroon

ZaLo House Waterline cabin with Hot Tub Pets

Todos Cabin

Maplewood Cabin, hideaway w/ hot tub + fireplace

Koselig Cabin: Lakefront cabin w/ stone beach

Rockhaven - Island View

Willsboro Point Waterfront Retreat
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Pocono Mountains Vacation rentals
- Québec City Vacation rentals
- The Hamptons Vacation rentals
- Capital District, New York Vacation rentals
- Waterfront rentals Chesterfield
- Rentals with lake access Chesterfield
- Rentals with a washer and dryer Chesterfield
- Rentals with a fire pit Chesterfield
- Rentals with a fireplace Chesterfield
- Family-friendly rentals Chesterfield
- Pet-friendly rentals Chesterfield
- Rentals with a patio Chesterfield
- House rentals Chesterfield
- Rentals with beach access Chesterfield
- Rentals with outdoor seating 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
- Lake Flower
- Fort Ticonderoga
- ECHO, Leahy Center for Lake Champlain
- Stowe Mountain Resort
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- Adirondak Loj
- Middlebury College
- University of Vermont
- Shelburne Museum
- Waterfront Park
- Lake Champlain Chocolates
- Shelburne Vineyard
- Boyden Valley Winery & Spirits
- Warren Falls
- Snow Farm Vineyard & Winery
- Elmore State Park
- Cold Hollow Cider Mill




