
House holiday rentals in Chesterfield
Find and book unique houses on Airbnb
Top-rated house rentals in Chesterfield
Guests agree: These houses are highly rated for location, cleanliness and more.

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.
LocationValueParking

"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!
ValueLocationIndoor spaces

Modern, hilltop, lakeside retreat!
A minimal, refined retreat nestled in trees offers peaceful, modern luxury. Use the dock for swimming and relaxing, kayaking, and paddleboarding. Built in 2021 to the highest standards, for extended family. Located about 15 minutes from downtown Burlington & downtown Winooski w/ access to all manner of outdoor & maritime activities! We encourage you to enjoy coffee on the dock in the morning! Views from the house vary with the season due to the leaves on the trees. The lake is always beautiful.
ValueLocationLaundry

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.
FamilyValueLayout

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.
ValueLocationGetting around

So. Burl. quiet setting 10 mins fr. everything
Burlington ski house, recently completely renovated. Located 10 minutes from downtown Burlington and the water front. One hour from most ski resorts puts you in the middle of all the action. Pet friendly! Dog door with fully fenced in yard for your pets to run. Beautiful new Artesian Elite hot tub to relax in with open air gazebo to enjoy year round. Large open kitchen/living room concept to entertain with. Wheel chair ramp accessibility. 2 bedrooms and a pull out sofa in the living room
FamilyLocationHospitality

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.
LocationValueNearby

ADK Summer Hub: Hot Tub-Game Rm-Coffee Bar-Dogs OK
Create unforgettable summer memories at Sugar House ADK Base Camp! Enjoy majestic, mountain views with family (including Fido!) and friends. Minutes from many hiking trails of all levels; just 23 min to Lake Placid. Spend the day in the great outdoors and cool evenings sipping hot cocoa or coffee made your way fireside or in the hot tub. Cozy up with a movie or challenge loved ones to ping pong, billiards, or poker in this contemporary farmhouse featuring a full kitchen and coffee bar.
ValueLocationHospitality

4CR Farm Guest House 4 Season Vacation Destination
We are conveniently located within 45 mins of 3 great ski - snowboard mountains, a water park, zip lining, wineries, breweries, and shopping. A 10 minute walk will get you to The Long Trail, to do some hiking. The Lamoille Valley Rail Trail is another great trail for walking and biking. Vermont also has over 100 covered bridges for you to explore. Our guest house is the perfect little spot to call home while in Vermont. Come and enjoy the peace and quiet of our county setting.
ValueFamilyCheckout

The Spring Hill House
Escape to a haven of natural beauty and tranquility at The Spring Hill House. Our unique bow roof home offers breathtaking views of Camel’s Hump and the majestic Green Mountains, the perfect setting for a rejuvenating getaway. Despite being removed from the hustle and bustle of city life, The Spring Hill House is still centrally located, providing easy access to some of Vermont's most popular destinations. Please note: We have a firm no kids policy due to the open loft and stairs.
LocationValueView

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.
ValueFamilyCheckout

Gorgeous Renovated Barn 20 minutes from Burlington
Historic renovated barn 20 minutes from Burlington, next to best cycling routes of Vermont, lake Champlain, beaches, hiking trails, orchards, wineries and farm to table restaurants. 30 to 60 minutes from Bolton (30min), Sugarbush (50min) and Stowe (60min). Ideal for a family of 4 or 5, or two couples. A 5 minute walk from a country store and deli and a 5 minute drive from the Essex, New York ferry. Beautiful indoor and outdoor fireplace.
LocationFamilyAmenities
Popular amenities for Chesterfield house rentals
House rentals with a pool

EPIC Stowe Getaway - Great For Families & Friends
FamilyValueOutdoor spaces

Serene Mountain Studio Spruce Peak Lodge | 1328
ValueFamilySkiing

Charming Sugarbush Standalone Condo
LocationValueAmenities

Mott House, South Hero Vermont
LocationFamilyOutdoor spaces

Catherine House
FamilyLocationBackyard

Whispering Maples
FamilyLocationQuiet

Ski in/out 3 Bedroom/3 Bath Sugarbush
FamilyValueComfort

Stunning Mountain Top Cabin
LocationFamilyKitchen
Weekly house rentals

Home away from Home
LocationValueAir conditioning

Luxury Urban Farmstay, centrally located
LocationFamilyParks

Camp Wildwood
LocationFamilyLayout

Quiet Adirondack Retreat with MASSIVE Views
ValueFamilyQuiet

The Mountain waits
LocationValueAir conditioning

Highlands Landing -Lakeside Getaway with Sauna!
LocationFamilySleep quality

Adirondacks 46 peaks LakeChamplain Retreat
FamilyValueIndoor spaces

High Peaks Haven
FamilyValueOutdoor spaces
Private house rentals

Gracious living
FamilyLocationQuiet

Home away from home
LocationFamilyWi-Fi

Late Summer and Fall specials. Adirondack fun.
LocationFamilyView

Heart of Malletts Bay home
LocationFamilyAir conditioning

Bittersweet Retreat on Willsboro Point
LocationFamilyLayout

Shelburne Bay Lakefront Home w/ Private Beach
LocationValueCheckout

Uniquely Designed Escape-Near Waterbury and Warren
LocationHospitalityIndoor spaces

The Nestled Nook Cottage
HospitalityAmenitiesComfort
Destinations to explore
- New York City Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Quebec City Holiday rentals
- Niagara Falls Holiday rentals
- Portland Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Mont-Tremblant Holiday rentals
- Newport Holiday rentals
- Providence Holiday rentals
- Bar Harbor Holiday rentals
- Sugarbush Resort
- Bolton Valley Resort
- Stowe Mountain Resort
- Fort Ticonderoga
- University of Vermont
- Middlebury College
- Lake Flower
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- ECHO, Leahy Center for Lake Champlain
- Snow Farm Vineyard & Winery
- Shelburne Museum
- Warren Falls
- Shelburne Vineyard
- Cold Hollow Cider Mill
- Elmore State Park
- Waterfront Park
- Boyden Valley Winery & Spirits
- Lake Champlain Chocolates
- Green River Reservoir State Park
- Ethan Allen Homestead Museum
- Branbury State Park
- Titus Mountain Family Ski Center
- Little River State Park
- Alburg Dunes State Park





