
Holiday rentals with a kayak in Chesterfield
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Top-rated Accommodation with a Kayak in Chesterfield
Guests agree: these holiday homes with a 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 summer retreat tucked among the trees on the shores of Lake Champlain’s Mallets Bay. Built in 2021, this serene and stylish hideaway is perfect for peaceful mornings, paddleboarding adventures, and evenings around the Solo Stove. Charge your EV while you watch the sunrise from the dock, sip local coffee with lake views, or explore nearby Burlington and Winooski—just 15 minutes away. Whether you're unwinding on the deck or enjoying the water, this is your perfect summer escape.

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.

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. Pet friendly-fee applies.

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.

4-Season Treehouse @ Bliss Ridge; Best Views in VT
thermostat control! LUXURY! 1-of-a-kind, 5⭐️Interior bathroom, @Bliss Ridge - 88acre, OG farm, private estate surrounded by 1000s acre of wilderness. NEW SAUNA& cold plunge!!! Our 2 architectural wonders = real treehouses, built withIN the living trees, not stilted cabins. Equipped w. a fabulous yotel fireplace, indoor hot shower / plumbing, fresh mtn spring water, stable access ramp. Our original Dr. Seuss treehouse, "The Bird’s Nest" is open May-Oct. WiFi avail at the barn! Cell svc works!

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.
Popular amenities for Chesterfield kayak rentals
Holiday House Rentals with a Kayak

Spacious Lakefront Retreat w/Stunning Views

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

Lake Champlain-Adirondack Mountains

Tranquil lake house in VT w/ breathtaking views

Birchwood Lodge - Our Home in the Woods

Bike Path BNB 3 bdrm 1.5 bath Spacious Comfortable

Lakeview Cottage

Recreate and relax by the lake!
Cottages with a kayak

Lakefront Cottage near Smugglers Notch Vermont

Keeler Bay Lakefront 1BR Cottage (Otter Creek)

Camel's Hump Remote Mountain Cottage

ADK Cozy River Cottage

Pearl of the Mountain

Camp Knotty and Nice at Minerva Lake. In the Adk

Storybook Cottage in the Champlain Islands

Waterfront Cottages at Wally’s Point
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"

Rockhaven - Island View

Willsboro Point Waterfront Retreat

Lake Placid Area-Bellas Cabin, Dog Friendly!

Adirondack A-Frame LakeChamplain
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 $249 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Chesterfield holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Chesterfield rentals

4.9 Average rating
Chesterfield stays are highly rated by guests—averaging 4.9 out of 5!
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- Sugarbush Resort
- Parc Safari
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Autumn Mountain Winery
- Ethan Allen Homestead Museum
- Leahy Center for Lake Champlain
- Cozy Cottages & Otter Valley Winery
- Burlington Country Club
- Country Club of Vermont
- Vermont National Country Club
- Lincoln Peak Vineyard
- Shelburne Vineyard
- Snow Farm Vineyard & Winery
- Titus Mountain Family Ski Center
- Boyden Valley Winery & Spirits
- Spruce Peak
- North Branch Vineyards
- Smugglers' Notch Resort




