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House vacation rentals in Chesterfield

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Top-rated house rentals in Chesterfield

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

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Top guest favorite
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

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.

LocationValueCleanliness

4.93 out of 5 average rating, 383 reviews
Guest favorite
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

"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!

ValueFamilyCheck-in

4.97 out of 5 average rating, 118 reviews
Top guest favorite
The living area features a modern design with a cozy gas fireplace centered on a dark accent wall. Large windows frame views of the surroundings, while comfortable seating includes a plush couch and various armchairs. Natural light illuminates the space, enhancing its inviting feel.
Home in Grand Isle

Stylish modern lakehouse w/ Hot tub, Firepit & Gym

Welcome to the Aviary Island Lakehouse! Your dream getaway in the heart of the Champlain Islands. This newly renovated lakehouse in Grand Isle is located just 30mins outside of Burlington. Designed to be modern, light and airy but still cozy and comfy; a blend of style and comfort. Wake up to sunrises over Lake Champlain and Green Mountain views. As a sister location to the Aviary Burlington, rest assured you can expect the same delightful design, attention to detail and abundant amenities.

ValueFamilyBiking

5.0 out of 5 average rating, 101 reviews
Top guest favorite
A bright living room features a large sectional sofa adorned with colorful accent pillows. A wooden coffee table with a glass top sits on a vibrant floral area rug, while natural light filters through a sheer window covering, illuminating the space.
Home in South Burlington

Luxury Urban Farmstay, centrally located

Enhance your visit to our beautiful Green Mountain State with a unique housing experience-rent a private home on Woods Edge Farm. 10 minutes from downtown Burlington, UVM & the airport, this tiny urban farm is tucked in a quiet residential neighborhood backed by woods & trails. Your stay won’t lack amenities: fully equipped chef’s kitchen, backyard patio, Roku tv. Beyond the private patio, wander onto the farm to pick your own berries for breakfast or arrange a tour with farmer/chef/host Anne.

LocationFamilyBreakfast

4.99 out of 5 average rating, 248 reviews
Top guest favorite
The lake house is set against a serene backdrop of trees, featuring a spacious porch with seating for relaxation. A flag is displayed from the front, and the structure is illuminated by soft lighting, enhancing the inviting atmosphere at dusk.
Home in Willsboro

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.

FamilyValuePets

4.95 out of 5 average rating, 122 reviews
Top guest favorite
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

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.

LocationFamilyBiking

4.98 out of 5 average rating, 250 reviews
Top guest favorite
Home in Au Sable Forks

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.

FamilyLocationCheckout

4.83 out of 5 average rating, 236 reviews
Top guest favorite
The exterior of the chalet is showcased, highlighting a welcoming entryway with a wooden deck and a pathway made of stones leading towards the lush greenery. The backdrop features rolling mountains under a clear blue sky, enhancing the natural setting.
Home in Wilmington

Stunning Views, Luxury, Near Whiteface,Lake Placid

LOOKOUT MOUNTAIN CHALET – Luxury 4 bedroom, 3 bathroom retreat just 1.9 mi to Whiteface 🎿 and 20 minutes to Lake Placid! Sleeps 10 in 4 beds plus queen foam mattresses 🛏. Dog-friendly 🐾, hot tub ♨, Finlandian sauna 🧖‍♂️, fireplace 🔥, direct mountain views 🌄 Enjoy the BBQ park-style BBQ grills; large deck, Trex furniture, spacious, custom bathroom showers, Smart TVs, and fully equipped kitchen with granite counters. Close to hiking and biking trails, lakes, dining, and year-round fun!

ValueFamilyQuiet

4.98 out of 5 average rating, 334 reviews
Top guest favorite
A stunning aerial view captures the farmhouse and surrounding farmland enveloped in a soft morning mist. The sun rises over distant hills, illuminating the landscape and creating a serene atmosphere. Farm buildings are visible amidst the lush greenery.
Home in South Burlington

Comfy Vermont Farmhouse

We invite all visitors to feel at home on the farm. Your stay in this newly renovated 3 bdrm farmhouse can be truly nourishing. Enjoy a fully equipped kitchen, comfy beds, 55" TV, Record Player, games, and walking access to our beautiful Organic Farm and Café. The views are simply stunning in all seasons. Conveniently located 10 minutes from Burlington, the beaches of Lake Champlain, and UVM. In under 30 minutes you can be hiking in the Green Mountains or swimming in local swimming holes.

FamilyLocationOutdoor spaces

4.97 out of 5 average rating, 109 reviews
Top guest favorite
A bright living area features a cozy orange sofa and a wooden rocking chair. A large wall-mounted photograph of a snow-covered mountain adds visual interest. A dining table is positioned in the foreground, with a floral arrangement on display.
Home in Burlington

Déjà View: Beautiful Home with Views of the Lake

Newly renovated, historic home with modern features and designs. Our home is located in downtown Burlington and features a wall of windows with spectacular lake and mountain views. The Lake Champlain waterfront and Battery Park are a short 10-15 minute walk away, while the top of Church Street is a 15-20 minute walk. Our 4 bedroom, 2 bath home is great for families and quiet guests as it is nestled in a quiet neighborhood oasis. The backyard has plenty of space to enjoy the sunsets.

LocationFamilyHospitality

4.94 out of 5 average rating, 176 reviews
Top guest favorite
A welcoming living area is displayed, featuring a leather couch and a second seating option with a cozy fabric in a muted tone. A coffee table is centered on a patterned area rug, complemented by plants and wall art. A TV is positioned on the entertainment unit, with natural light filtering through the windows.
Home in Winooski

Artsy Bungalow

This newly renovated artsy bungalow offers a convenient, peaceful and stylish place to stay while exploring the Burlington/Winooski area. The 3 bed 1 3/4 bath home is nestled on a quiet street in vibrant Winooski. The home is a 10 minute drive to downtown Burlington & the airport, and a short walk to the river, several cafes, restaurants, pubs, and a brewery. Winooski is referred to as “the Brooklyn of Burlington” because of the foodie scene and rich cultural diversity.

LocationValueAir conditioning

4.95 out of 5 average rating, 100 reviews
Top guest favorite
A sprawling meadow extends towards distant mountains, with a varied landscape marked by trees and fields. The sky is partially covered with clouds, offering a serene view of the natural surroundings and hints of autumn colors in the foliage.
Home in Wilmington

THE VIEW! THE VIEW! THE VIEW!

A 1900 farmhouse that has been in the family for generations. Recently renovated to accommodate up to 5 guests, it is clean with simple furnishings and a SPECTACULAR VIEW! Located RIGHT ON NYS RTE 86 (close to the road) with easy access to nearby attractions. The house is split in 2 and is designed for 2 families. I rent out "The View" using airbnb exclusively. My wife and I reside in the back portion of the house with a separate entrance and separate parking.

FamilyValueBackyard

4.95 out of 5 average rating, 565 reviews

Popular amenities for Chesterfield house rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favorite
The exterior of a two-story home is shown, featuring dark wood siding with red accents. Snow covers the ground in front, while a wooden balcony extends from the upper level. Ski equipment leans against the house, and a few evergreen trees are visible in the background.
Home in Wilmington

The Brookside @ Wilmington, NY

FamilyLocationQuiet

4.96 out of 5 average rating, 255 reviews
Top guest favorite
A spacious two-story home is set among lush greenery, with a large front deck featuring white railings. The exterior showcases a mix of light-colored siding and dark shutters, while tall trees provide a natural backdrop, creating a peaceful atmosphere.
Home in Stowe

EPIC Stowe Getaway - Great For Families & Friends

FamilyValueBiking

4.98 out of 5 average rating, 315 reviews
Guest favorite
A modern stand-alone condo is set against a backdrop of vibrant autumn foliage. The light gray exterior features large windows, allowing natural light to fill the interior. A wooden deck and stairs lead to the entrance, surrounded by well-maintained landscaping.
Home in Warren

Charming Sugarbush Standalone Condo

ValueLocationQuiet

4.83 out of 5 average rating, 132 reviews
Superhost
Home in Keeseville

High Peaks Haven

ValueFamilyAccuracy

4.69 out of 5 average rating, 108 reviews
Guest favorite
A quaint two-story house is set against a backdrop of lush greenery. The exterior is painted in a soft green hue, complemented by white railings and a spacious front porch. The surrounding landscape features tall grass and a clear sky, enhancing its serene appeal.
Home in South Hero

Mott House, South Hero Vermont

FamilyValueTV

4.97 out of 5 average rating, 62 reviews
Guest favorite
A living area features a comfortable gray sofa and a reclining chair, arranged around a wooden coffee table. A patterned area rug and a stone fireplace add warmth, while large windows allow natural light. Decorative shelves display various items, enhancing the welcoming environment.
Home in Plattsburgh

Catherine House

LocationFamilyNearby

4.92 out of 5 average rating, 12 reviews
Guest favorite
Home in Fairfield

Sugar House Homestead: A Perfect Retreat

FamilyLocationIndoor spaces

5.0 out of 5 average rating, 12 reviews
Top guest favorite
An open-concept living area features a modern kitchen with a spacious island bar and seating for four. Natural wood cabinetry contrasts with stainless steel appliances. A comfortable sitting area is located adjacent, with a minimalist coffee table and a wall-mounted TV enhancing the functionality of the space.
Home in Mooers Forks

Whispering Maples

LocationFamilyCheck-in

4.97 out of 5 average rating, 38 reviews

Weekly house rentals

Guest favorite
An aerial view captures a quaint farmhouse situated near the Ausable River, surrounded by lush greenery and hills. The structure features a sloped roof and a front porch, set against a backdrop of rolling mountains and open fields.
Home in Jay

The Jay House - 1840 Farmhouse

LocationFamilyAccuracy

4.94 out of 5 average rating, 162 reviews
Top guest favorite
A modern living area is captured with large windows providing natural light and views of the surrounding trees. A gray sectional sofa faces a sleek coffee table, with a brown leather armchair nearby. The streamlined kitchen features a gray countertop and minimalist design elements.
Home in Malletts Bay

Modern, hilltop, lakeside retreat!

LocationFamilyLaundry

4.99 out of 5 average rating, 139 reviews
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

Modern House on Lake Champlain

LocationFamilyBackyard

5.0 out of 5 average rating, 63 reviews
Top guest favorite
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

Quiet Adirondack Retreat with MASSIVE Views

LocationValueDecor

5.0 out of 5 average rating, 69 reviews
Guest favorite
The charming red chalet is surrounded by lush greenery, featuring a grassy lawn and a wooden deck with a red umbrella. A welcoming wreath adorns the front door, and steps lead to the elevated deck, enhancing the connection to the natural landscape.
Home in Keeseville

Adirondacks 46 peaks LakeChamplain Retreat

LocationFamilyHospitality

4.84 out of 5 average rating, 37 reviews
Guest favorite
Several colorful canoes and kayaks are arranged along the grassy shore, with yellow, red, and white hulls visible. A blue canopy stands nearby, providing shade over a seating area. The calm lake reflects the surrounding greenery and cloudy sky in the background.
Home in Keeseville

Magical Augur Lake Retreat-Great for Large Groups!

FamilyLocationNearby

4.98 out of 5 average rating, 64 reviews
Guest favorite
A silhouette of a house extends toward the lake, framed by tall trees. A spacious deck is visible in the foreground, overlooking serene water reflecting soft colors from the sunset sky. Gentle clouds are scattered, creating a tranquil atmosphere.
Home in Keeseville

Camp Wildwood

FamilyLocationHiking

4.94 out of 5 average rating, 31 reviews
Guest favorite
A charming one-story house features a combination of wooden and stone exteriors. The sloped roof is clad in metal, while large windows offer natural light. A paved pathway leads to the front door, surrounded by green grass and landscaped flower beds.
Home in Keeseville

The Mountain waits

LocationFamilyLayout

4.95 out of 5 average rating, 41 reviews

Private house rentals

Guest favorite
A lakeside view showcases a charming house with lush trees and stone landscaping along the waterfront. The interior image features a dining area with a wooden table and chairs, framed by large windows that provide expansive views of the lake and landscape.
Home in South Burlington

Shelburne Bay Lakefront Home w/ Private Beach

ValueFamilyAccuracy

4.94 out of 5 average rating, 50 reviews
Guest favorite
A serene outdoor seating area features four woven chairs and a round glass table, positioned on a stone patio overlooking Lake Champlain. The expansive view includes gentle waves and boats in the distance under a partly cloudy sky.
Home in Malletts Bay

Chic Modern Lake Getaway!

FamilyValueSleep quality

4.9 out of 5 average rating, 80 reviews
Top guest favorite
Home in Jay

Don’t miss the Fall Colors! Book now!

FamilyLocationHot tub

4.98 out of 5 average rating, 87 reviews
Guest favorite
Home in Burlington

Burlington House- New North End-Monthly Rental

ValueLocationAccuracy

4.9 out of 5 average rating, 21 reviews
Top guest favorite
A modern living room features a spacious white sofa paired with two armchairs. A wooden coffee table sits in the center, surrounded by shelves filled with books and decorative items. Large windows allow natural light to illuminate the space, while a sleek wood-burning stove adds warmth.
Home in Charlotte

Architectural Modernist Cabin - Bauschaus VT

LocationFamilyDecor

5.0 out of 5 average rating, 50 reviews
Top guest favorite
Home in Jay

Jay Mountain Views•Fenced yard•Trails•Lean-to

FamilyLocationCondition

5.0 out of 5 average rating, 18 reviews
Top guest favorite
Home in Peru

ZaLo Manor Unit Lakefront hot tub, pets

FamilyLocationOutdoor spaces

4.97 out of 5 average rating, 35 reviews
Guest favorite
A modern kitchen features wooden cabinetry and a central island with a granite countertop. Three chairs are positioned at the island, and stainless steel appliances, including a refrigerator and dishwasher, are visible. The space is well-lit, offering a functional cooking environment.
Home in Malletts Bay

Heart of Malletts Bay home

FamilyValueAmenities

4.99 out of 5 average rating, 67 reviews

Destinations to explore