
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!

Camel's Hump Remote Mountain Cottage
Escape to this peaceful getaway with beautiful mountain views. Our cottage is ideal for the adventure seeker, nature lover or remote worker. Located less than two miles from Camel’s Hump trail head and less than 30 miles from ski resorts, including Stowe, Sugarbush, Bolton, Cochran and Mad River. The area offers plenty of outdoor activities from hiking, cross country skiing, snow shoeing, mountain biking, fishing, swimming, kayaking and only 15 min from local restaurants, breweries and shops.

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 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!

Grand Suite w/ Backyard Access on Mirror Lake
Welcome to your home away from home in the heart of the Adirondacks! This modern oversized studio offers top-of-the-line amenities, including an oversized shower, and a spacious balcony perfect for morning coffee or evening relaxation. Located just steps above the village, our apartment is surrounded by scrumptious food options, boutiques, and parks. Explore the iconic small town or enjoy a tranquil evening in your peaceful haven. Book your stay with us today for a memorable urban escape!

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.

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

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

Lake Champlain Waterfront Getaway w/ Sunset 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

Spectacular views at the “Edge” of Lake Champlain

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

Keeler Bay Lakefront 1BR Cottage (Otter Creek)

Gorgeous lakefront home close to Burlington!

Pearl of the Mountain

Gone Fishing! Is Pet Friendly! Now with 4 kayaks!

Storybook Cottage in the Champlain Islands
Cabin rentals with a kayak

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

Quaint Cabin in Schroon

Lake Iroquois - "Lakes End"

Maplewood Cabin, hideaway w/ hot tub + fireplace

Rockhaven - Island View

Willsboro Point Waterfront Retreat

Cabin With a Giant View

Lake Placid Area, Dukes Cabin-Dog Friendly!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal 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
- Waterfront rentals Chesterfield
- Rentals with outdoor seating Chesterfield
- Family-friendly rentals Chesterfield
- Rentals with beach access Chesterfield
- Rentals with a firepit Chesterfield
- Rentals with a patio Chesterfield
- Rentals with a fireplace Chesterfield
- House rentals Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Pet-friendly 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
- Whiteface Mountain Ski Resort
- Bolton Valley Resort
- Lake Flower
- Fort Ticonderoga
- ECHO, Leahy Center for Lake Champlain
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- University of Vermont
- Stowe Mountain Resort
- Adirondak Loj
- Shelburne Museum
- Shelburne Vineyard
- Snow Farm Vineyard & Winery
- Boyden Valley Winery & Spirits
- Waterfront Park
- Lake Champlain Chocolates
- Middlebury College
- Warren Falls
- Elmore State Park
- Cold Hollow Cider Mill




