Holiday rentals in Chesterfield

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Top guest favourite
A modern wooden exterior features a combination of large windows and a welcoming front door. The building includes two spacious garage doors, all set against a backdrop of colorful autumn foliage. A manicured pathway leads to the entrance.
Loft in Keeseville
5 out of 5 average rating, 220 reviews

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.

Guest favourite
A cottage is seen perched on a grassy bank, overlooking a river. Tall trees frame the scene, providing a natural backdrop. The water's surface reflects the surroundings, while a hint of light is visible from the cottage window, suggesting warmth inside.
Home in Willsboro
4.97 out of 5 average rating, 116 reviews

"Beau Overlook" Enjoy 2 states from 1 great spot!

Come enjoy LOGISTICS to the Green Mountains of VT & the heart of the DACKS in one sweet spot. "Beau Overlook Cottage" perched high on the banks of the BOQUET RIVER, with sweet sounds of water tumbling over river rocks below. This home is situated 2 miles north of the Lake Champlain ~ Boquet River Delta. The beautiful LAKE scene at the sandbar of the delta must be seen to be appreciated. This relaxing sanctuary will provide an upscale and sophisticated home, whose logistics cannot be beat!

Top guest favourite
The cabin features a charming exterior with wooden siding, a shingled roof, and decorative trim. Large windows allow natural light to fill the interior. A stack of firewood is neatly arranged beside the entrance, which is framed by vibrant landscaping.
Cabin in Au Sable Forks
4.98 out of 5 average rating, 223 reviews

Moon Ridge Cabin *Hottub*

Our cabin is a studio with a hot tub & all the amenities. A queen bed, linens, towels, small refrigerator/freezer, microwave, single burner cook plate, dishes, utensils, glassware, pots/pans, toaster & coffee maker. Roku Tv & dvd player w/movies. The cabin has both an inside & outside (summer)shower. We have a privacy fence between our home & cabin. In the back yard you will find hot tub, firepit & screen house. Enjoy your stay! *Also check out our off grid camping cabin The Firefly on airbnb.

Top guest favourite
A modern cabin is nestled among tall trees, elevated on stilts. Large windows offer a glimpse of the interior space, featuring a minimalist design. The surrounding greenery creates a natural setting, while the pathway leading to the cabin is lined with earth tones.
Cabin in Morristown
5 out of 5 average rating, 260 reviews

Cady’s Falls Cabin

Welcome to our treehouse inspired, modern cabin overlooking The Kenfield Brook on Terrill Gorge. We are located 5 miles from Stowe and its attractions, and just a few minutes from downtown Morrrisville with all its amenities. Just upstream from the picturesque Cady’s Fall swimming hole and across the brook from the amazing Cady’s Falls bike trails, our cabin is perched atop the hillside. With its simple, minimalist design it’s easy to immerse yourselves in nature and feel at home in the trees.

Top guest favourite
A charming chalet stands amidst a wooded area, with warm interior lights glowing through the large front windows. A stone fire pit is surrounded by wooden Adirondack chairs, creating a cozy outdoor gathering space under strung lights scattered among the trees.
Cabin in Jay
4.99 out of 5 average rating, 162 reviews

TheADKChalet w/ Hot Tub (Adirondacks)

At face value, IG: @theadkchalet appears to be just a humble little getaway tucked in the Adirondack Mountains of Jay, NY (Lake Placid Area). But even the most discerning guests will be quickly spirited away by the rustic charm and secluded forest feel. The Chalet sleeps 4 people and has two bedrooms and one bathroom. The Chalet is located approx. 4.5hrs from NYC by car and is the perfect place to: escape the city, rekindle a romance, ski/ride Whiteface Mountain, hike, fish and so much more!

Top guest favourite
A rustic cabin is framed by lush greenery, surrounded by a manicured garden. An outdoor picnic table is situated on the grass, complemented by a patio umbrella and flower pots. The entrance features a welcoming door, adding charm to the serene woodland setting.
Place to stay in Peru
4.93 out of 5 average rating, 174 reviews

The Brookside Cabin

Our Cabin is nestled in the woods of the Adirondack Mountains. The Cabin is behind our family home. We are on a country road close to two towns. Our area offers many amenities such as fishing, hiking, boating, golf, hunting , wine tasting, leaf peeping. The cabin is heated by a wood stove and is the only heat source. “Wood Stove will injure a small child. Fast moving water in brook. Children 7 and up is ok with pre approval. The outside shower is heated, hot water available mid April -Nov.

Top guest favourite
Sunlight filters through tall trees, casting elongated shadows on a grassy area by the lake. The serene water reflects the sky, creating a peaceful atmosphere. A few chairs are positioned on the grass, inviting relaxation and enjoyment of the picturesque surroundings.
Home in Willsboro
4.95 out of 5 average rating, 113 reviews

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.

Top guest favourite
An aerial view captures the cozy chalet nestled among lush green trees, with distant mountain peaks visible in the background. The cabin is surrounded by a spacious outdoor area, showcasing a wrap-around deck that invites relaxation.
Cabin in Jay
4.96 out of 5 average rating, 260 reviews

Adirondack Timberwolf Cabin

Cozy Mountain Chalet in Jay, NY on beautiful Glen Road. Only .7 miles to the Jay Covered Bridge, 3 miles to the Jay Mountain summit trail head, 7 miles to Whiteface Mountain, and 16 miles to Lake Placid. Keene and Keene Valley trail heads are only minutes away. The cabin has 3 acres of wooded property with a front driveway as well as a back access drivweway which is nice to walk. There is Satellite TV and wifi. There is good cell coverage. World Class Fishing, Ausable Rivers are close

Top guest favourite
Cottage in New Haven
4.99 out of 5 average rating, 193 reviews

Hilltop Cottage With a View

Our newly built cozy and relaxing guest cottage is located in New Haven . It has stunning views and gorgeous sunsets!! Located just seven miles from Middlebury ,Vergennes and Bristol . All of which have great shops and restaurants! Close to many local attractions including ,Woodchuck Cider house, Lincoln Peak Vineyard, Ski areas, Hiking , rivers, lakes, restaurants and much more! Our goal was to provide guests with a home away from home! We feel our cottage offers that and much more.

Top guest favourite
The cabin exterior is illuminated by soft lighting, highlighting the wooden structure surrounded by trees. A cozy fire pit area with red chairs, a picnic table, and an umbrella is visible, creating an inviting outdoor space for relaxation and gathering.
Cabin in Wilmington
4.99 out of 5 average rating, 330 reviews

JUNIPER HILL cabin

Juniper Hill cabin is a new construction two bedroom/one bathroom home situated in Wilmington, NY. This cabin sits in the heart of the Adirondack mountains and is minutes to outdoor adventure of all kinds! Only five minutes to Whiteface Mountain and less than 15 minutes to downtown Lake Placid, the convenience of the location is key for both outdoor enthusiasts and those looking to just getaway and relax in nature. The Ausable River and Lake Everest are both within walking distance.

Guest favourite
The living room features a cozy seating area, including a light gray sofa and a recliner. Large windows with sheer curtains allow natural light to fill the space, while wooden accents, including a unique table, add character to the setting.
Flat in Jay
4.94 out of 5 average rating, 136 reviews

"Gateway To The Adirondacks" on Main Street

Situated in the heart of the village on Main Street in Au Sable Forks, the "Gateway to the Adirondacks", you'll find this newly renovated second floor apartment. This spacious unit offers a fully equipped kitchen, two bedrooms, full bath and comfortably furnished living room with Smart TV and WiFi. Conveniently located within walking distance to grocery stores, pub, eateries, and entertainment. Enjoy fishing, biking, hiking, Whiteface Mountain and Lake Placid.

Guest favourite
A modern house with wooden exterior is shown from an elevated perspective, surrounded by autumn foliage. A hot tub is positioned on a spacious deck, which includes a seating area with four chairs and a small table. Scenic mountain views and vibrant trees enhance the natural setting.
Tiny home in Warren
4.99 out of 5 average rating, 303 reviews

Luxury Glass Tiny House - Mountain View + Hot Tub

Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet. *One of Airbnb’s Most Wish-listed Stays of 2023*

Popular amenities for Chesterfield holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Essex County
  5. Chesterfield