Holiday houses in Chesterfield

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Top-rated holiday rentals in Chesterfield

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

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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
5.0 out of 5 average rating, 232 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 favourite
The exterior of a wooden house is displayed, featuring a sloping entrance with a wooden walkway leading to the main entry. Large windows provide views of the lake and surrounding greenery, while colorful flower beds enhance the peaceful setting.
Home in Port Kent
4.93 out of 5 average rating, 379 reviews

18 Lake Stunning View of Champlain in Adirondacks

Welcome to 18 Lake. Situated in beautiful, quiet, Port Kent, NY, this gem is the perfect place to relax and get away. People come from all across the country to tour this charming area on bicycles in summer, and from all over the world during the winter for Lake Placid's winter sports. In fall, the colors are vibrant and breathtaking. Fresh maple products are on tap in Spring. Enjoy area attractions such as Ausable Chasm, High Falls Gorge, Port Kent Beach, golf, orchards, hiking and biking.

Top 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, 118 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
Place to stay in Peru
4.93 out of 5 average rating, 193 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
A queen-sized bed is positioned against a wooden wall with slanted ceilings. Large triangular windows provide views of the surrounding forest and mountains, allowing natural light to fill the space.
Home in Keene
4.98 out of 5 average rating, 245 reviews

Ascent House | Keene

A unique retreat meticulously crafted for resting and recharging after exploring in our beautiful Adirondack Wilderness. Flooded with natural light, every room offers calming frames of nature. Watch the sun peak through the forest and rise over the mountains through expansive windows. Ascend the levels of the house, each revealing more landscape. Experience a designer woodfired traditional Finnish sauna & totally recharge while embracing our harsh Adirondack weather. We hope you love it here.

Top Guest favourite
The exterior of a hillside home is showcased, featuring natural wood siding and multiple windows. A screened porch is evident, providing a view of the surrounding greenery and Lake Champlain in the distance. The well-maintained lawn enhances the tranquil setting.
Home in Keeseville
5.0 out of 5 average rating, 66 reviews

Quiet Adirondack Retreat with MASSIVE Views

Come rejuvenate at our Adirondack hilltop home on 7 acres overlooking Lake Champlain, Green Mountains of Vermont, and the Adirondack Park. **30 minutes from Whiteface Mountain skiing** Whether you are looking to reconnect with family/friends, unwind after a day of hiking/biking/skiing/golfing/leaf peeping in the Adirondacks or finish that book/album you are working on, you will find a quiet environment to relax and enjoy your break inside the Blue Line of the 6-million-acre Adirondack Park.

Guest favourite
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
5.0 out of 5 average rating, 60 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.

Top Guest favourite
The front of the cabin is framed by lush greenery and features a welcoming red door. Around a cozy patio area, four classic Adirondack chairs are arranged, complemented by blooming flower pots offering vibrant colors.
Cabin in Keeseville
4.93 out of 5 average rating, 160 reviews

Adirondack Cabin Retreat – Hot Tub + Lake

Plan a peaceful stay for up to 5 people in this cozy, well-appointed cabin with lake access that marries rustic charm with modern amenities. This is a vintage Adirondack retreat with access to a quiet and private lake perfect for swimming, paddling and fishing. We have loons and a resident bald eagle. A local winery and brewery are so close by too! Ausable Chasm is fun family-friendly attraction just down the road. Lastly for security, we have a camera focused on driveway entrance.

Guest favourite
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, 109 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 favourite
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
4.98 out of 5 average rating, 40 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 favourite
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, 381 reviews

Autumn 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 favourite
A landscaped pathway with natural stone steps leads to a rustic log cabin, framed by lush greenery. The cabin features a warm wooden exterior, complemented by a surrounding garden with various plants. A decorative bell is positioned near the pathway.
Cabin in South Hero
4.98 out of 5 average rating, 119 reviews

The Cabin @ The Birches

Nestled on the serene shores of Lake Champlain, this rustic log cabin offers the perfect escape from city life. Located at 41 Kibbe Farm Rd. in South Hero, VT, this idyllic retreat promises tranquility and natural beauty in abundance. Whether you seek a peaceful retreat or an adventure-filled getaway, this lakeside log cabin provides the perfect setting. Book your stay today and experience the beauty of Vermont from the comfort of your own cabin on Lake Champlain.

Popular amenities for Chesterfield holiday rentals