
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!

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.

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.

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.

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.

Four Pines on Lake Champlain
Our picturesque lakefront carriage house apartment offers spectacular mountain and lake views with stunning sunsets. A private beach for swimming and lounging, a patio, and a fire pit for unwinding and stargazing make for an ideal place to relax and recharge. Our high-speed internet is ideal for telecommuting and our location offers easy access to numerous outdoor activities - hiking, cycling, and skiing - with proximity to Burlington, VT, rated one of America’s Best Small Cities.

Adirondack Home
The Adirondack home is a cozy warm house, sitting on a 45 acres property in Schuyler Falls, NY with gorgeous surrounding nature located between lake champlain and whiteface moutain. If you’re looking to enjoy a nice sauna, a warm jacuzzi, and/or a relaxing night with fire on a clear sky, don’t hesitate to book. It is a haven for a couple romantic getaway, a skiing experience, or a relaxing family time in the Adirondack nature. Parties are not allowed for safety reasons.
Popular amenities for kayak rentals in Chesterfield
House rentals with a kayak

Spacious Lakefront Retreat w/Stunning Views

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

Lake Dunmore Oasis near Middlebury

Adirondacks, 15 min. to Gore Mt.

Lake Dunmore Getaway — Foliage Views & Ski Retreat

Birchwood Lodge - Our Home in the Woods

Summer View Lake House

Sauna, Dock & 180° Views – Lakefront Retreat
Cottage rentals with a kayak

Lakefront Cottage near Smugglers Notch Vermont

Waterfront Kayak and relax on Great Chazy River

Keeler Bay Lakefront 1BR Cottage (Otter Creek)

Gorgeous lakefront home close to Burlington!

Pearl of the Mountain

Camp Knotty and Nice at Minerva Lake. In the Adk

Storybook Cottage in the Champlain Islands

Cozy cottage at “The 588 By The Lake”
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"

Tamarac Romantic Waterfront Cabin For Two.

Rockhaven - Island View

Willsboro Point Waterfront Retreat

Lake Placid Area-Bellas Cabin, Dog Friendly!
Quick stats about holiday rentals with a kayak in Chesterfield

Total holiday rentals
Explore 20 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at $180 SGD per night before taxes and fees

Verified guest reviews
Over 960 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Chesterfield holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesterfield rentals

4.9 Average rating
Chesterfield stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
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- Rentals with a firepit Chesterfield
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- Rentals with lake access Chesterfield
- Rentals with a patio Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Family-friendly rentals Chesterfield
- House rentals Chesterfield
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- Rentals with beach access Chesterfield
- Rentals with a kayak Essex County
- Rentals with a kayak New York
- Rentals with a kayak United States
- Sugarbush Resort
- Parc Safari
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Autumn Mountain Winery
- Country Club of Vermont
- Burlington Country Club
- Ethan Allen Homestead Museum
- ECHO, Leahy Center for Lake Champlain
- Vermont National Country Club
- Lincoln Peak Vineyard
- Titus Mountain Family Ski Center
- Shelburne Vineyard
- Snow Farm Vineyard & Winery
- Boyden Valley Winery & Spirits
- North Branch Vineyards




