
Holiday rentals with a kayak in Chesterfield
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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.

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.

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 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!

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.

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.

Beautiful lake-front cottage, Lake Champlain
Lakefront cottage located in Highgate Springs, Vermont, on the Canadian border. The 2-bedroom cottage sits adjacent to the owner-occupied main house, on a large one-acre lot, with 120 feet of Lake Champlain shoreline. Enjoy the stunning sunset views while sitting on the deck overlooking the water. Private dock included. Montreal and Burlington each 45 minutes away. Available level-2 car charger. Well-behaved pets allowed. Super-fast WIFI!
Popular amenities for kayak rentals in Chesterfield
House rentals with a kayak

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

Lake Dunmore Oasis near Middlebury

Tranquil lake house in VT w/ breathtaking views

Adirondack Lake Retreat

Sunrise Lake House! Comfort-Hot Tub-Beach

Sauna, Dock & 180° Views – Lakefront Retreat

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

Lake Champlain Colonial
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

Gorgeous lakefront home close to Burlington!

Storybook Cottage in the Champlain Islands
Cabin rentals with a kayak

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

Historic Cabin Retreat - In Town and On the Lake!

Quaint Cabin in Schroon

Lake Iroquois - "Lakes End"

Maplewood Cabin, hideaway w/ hot tub + fireplace

Rockhaven - Island View

Willsboro Point Waterfront Retreat

Lake Placid Area, Dukes Cabin-Dog Friendly!
Destinations to explore
- Plainview Holiday rentals
- New York City 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
- Capital District, New York Holiday rentals
- Waterfront rentals Chesterfield
- Rentals with lake access Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Rentals with a firepit 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




