Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

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

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Top guest favorite
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, 223 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.

Top guest favorite
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, 235 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 favorite
Place to stay in Peru
4.93 out of 5 average rating, 183 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 favorite
A unique treehouse is seen perched among tall trees, with a blend of rustic wood siding and large windows that reflect the surrounding greenery. The structure stands elevated from the ground, supported by slender pillars, blending harmoniously with the natural forest environment.
Treehouse in Hancock
4.98 out of 5 average rating, 174 reviews

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

Top guest favorite
White Adirondack chairs are positioned near the river, offering a view of the flowing water and colorful autumn foliage. Trees displaying shades of orange and green line the riverbanks, creating a serene natural environment. The landscape is framed by a gently rolling background.
Apartment in Clintonville
4.96 out of 5 average rating, 184 reviews

Cozy Rustic Apartment

We are located on the famous Ausable River within a 30 minute drive to many of the High Peak trails, the beautiful Ausable Chasm, and Whiteface mountain. We are 5 miles from Interstate 87. The apartment can be a cozy retreat after spending a day exploring in the Adirondacks. Spend time strolling down to the river to enjoy the scenic views or enjoy quality downtime with family. The apartment has a unique style of its own that will provide you a comfortable and reasonable price place to stay.

Top guest favorite
A mid-century modern house is framed by vibrant autumn foliage. The structure features a sloped roof with a combination of white siding and metallic panels. An inviting balcony holds several Adirondack chairs, while a rock landscaping adds to the natural setting.
Home in Willsboro
5 out of 5 average rating, 58 reviews

Modern House on Lake Champlain

Unplug and unwind in this renovated mid-century-modern inspired house on Lake Champlain in the Adirondack Park. Enjoy privacy and nature on the 3.5 acre lot with 200 feet of shore. The bedrooms each have en-suite bathrooms. Relax in the soaking tub and watch a movie. Sink into an Adirondack chair, take in Mount Mansfield and be on the lookout for deer and other wildlife. Take a short hike through a cedar forest down to the shore. The house also serves as an art gallery for local artists.

Guest favorite
A charming off-grid cabin sits amidst lush greenery, featuring wooden walls and large windows. A small porch extends from the cabin, providing an inviting space. Trees surround the area, while soft sunlight filters through the branches, creating a serene atmosphere.
Cabin in Keeseville
4.95 out of 5 average rating, 106 reviews

Lovely Cabin on Farm with Sauna, Porch, Mtn Views

This tiny, off-grid cabin is situated on a peaceful, beautiful spot at a small, working livestock farm in the eastern Adirondacks. Your view looks west to Whiteface mountain etc. Enjoy the hum of nature from the porch that overlooks our pastures, and indulge in the small, traditional sauna and hot/cold outdoor shower that accompany your cabin. AuSable Brewery is just across the road, and Lake Champlain is just 1 mile away. Excellent local cycling, paddling, hiking, & boating abound.

Top guest favorite
The open-plan living area features a spacious sectional sofa positioned near a light-toned rug. Natural wood beams enhance the ceiling, while windows invite ample light. The fully-equipped kitchen, complete with modern appliances, is easily accessible, and a washer/dryer is visible in the adjacent area.
Guesthouse in Willsboro
4.97 out of 5 average rating, 34 reviews

The Farmhouse

Nestled in the rolling hills of the Adirondack Mountains, 'The Farmhouse' is a guest house attached to our home and provides a serene setting for you and your family. Hiking, camping, and woodland walks abound in the area, including a newly established trail less than 0.1 miles from the front door. Nearby Lake Champlain provides endless water oppourtunites, and Whiteface mountain, a 45 minute drive is a major ski and hiking destination. Ausable Chasm is a short 15 minutes away.

Top guest favorite
The exterior of the cabin is surrounded by lush trees, featuring a distinctive angled roof and large windows. A deck wraps around the house, leading to a fire pit area with Adirondack chairs. A winding path connects the cabin to a nearby hammock.
Chalet in Jay
4.96 out of 5 average rating, 365 reviews

Summer Forest Retreat | Hot Tub + Massage Chair

⭐ TOP 1% STAY — 300+ 5★ Reviews Guests often say: “This was exactly what we needed.” Welcome to Place of Prana — a peaceful Adirondack escape designed for rest, healing, and true reset. Summer weekends are filling quickly ☀️ Book your Adirondack escape before the season is gone. Are your dates unavailable? Explore our sister stay, Place of Poiema — another peaceful Adirondack retreat designed for gathering, connection, and unforgettable time together for 10 guests.

Top guest favorite
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, 320 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*

Superhost
A spacious deck overlooks the lake, featuring an outdoor dining area with a table and chairs. An umbrella provides shade, while flowers bloom nearby. Clear sky and water complement the tranquil setting, creating an inviting atmosphere for relaxation.
Home in Keeseville
4.87 out of 5 average rating, 30 reviews

Highlands Landing -Lakeside Getaway!

Take it easy at this unique and tranquil getaway on the shores of Lake Champlain. This home has privacy, a large wrap-around porch, direct water access, but is also close to local breweries, wineries, and great Adirondack hiking. Guests have access to kayaks, a sandy beach with fire pit (firewood included), and can lounge and swim off of a deep water dock! The home is great for families, couples, and friends looking to get away from it all!

Top guest favorite
Bright interiors are enhanced by skylights, allowing natural light to fill the space. A comfortable gray sofa is positioned beside a cheerful yellow chair, with a round ottoman nearby. Colorful curtains frame the window, while a white dining table offers seating for meals.
Cottage in Burlington
4.96 out of 5 average rating, 154 reviews

Brand New Cottage Near Burlington Park & Beaches

Built in 2024 and designed to complement the 1930s bungalow aesthetic of the main house, this cottage sits directly across from Ethan Allen Park with North Avenue beaches a short bike ride or drive away. Sleeps up to 4 with a queen bed in the bedroom and a queen pullout sofa in the living room. Skylights and lofty ceilings fill the space with natural light throughout. Well insulated with centrally ducted heat and A/C for year-round comfort.

Popular amenities for Chesterfield vacation rentals

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  2. United States
  3. New York
  4. Essex County
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