
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.

Aunt Shy's Hide-Away
Aunt Shy's hide-away is nestled on a dead end road in the Spruce Mill Brook Valley bounded by Saddle Hill and Hood Mountain (both on the 250-acre property). Situated in the Adirondack Park midway between the High Peaks and Lake Champlain (Exit 32 on I-87), this property is in an ideal base for enjoying the Adirondack Mountains and Lake Champlain Valley. Looking to get away from the daily grind, hike, bike, fish, ski, or just relax by the fire. Five minutes to the Meadowmount School of Music.

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.

"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!

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.

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.

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.

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

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.

The Crow's Nest | Beachfront home on Malletts Bay
The Crow's Nest is a stunning luxury listing on Malletts Bay. This new construction home offers a dream vacation experience for up to 7 guests. Situated directly on the beach at Malletts Bay, you can live the Vermont lake life with your toes in the sand, paddle boarding on the lake, or from the top-level primary suite, enjoying unparalleled views of Lake Champlain. Out of state travelers will love visiting Church Street in Downtown Burlington, a quick 20 minute drive from The Crow's Nest!

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.

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.

Convenient Cape | Explore Burlington & Stowe
Welcome to Convenient Country Living! We pride ourselves in offering up prime location, clean everything, and enough privacy to feel completely at home. Less than 5 min Williston shopping, I-89, fuel, restaurants, grocery, trails 10 min BTV, UVM, Hinesburg 15-20 min Downtown Burlington, Essex Junction, Shelburne, Richmond, Waterbury, Jericho, Bolton Valley, Cochrans <1hr Stowe, Sugarbush, Mad River Also ours: airbnb.com/h/the-hillside-hideaway
Popular amenities for house rentals in Chesterfield
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Steps to Golf and Mountain Biking

Mountain View Farmhouse w/ Orchard, Pool is Open!

Ranch at Mendon Mt Orchards

L'Absolut Lac Champlain, Venise-en-Québec

SugarBear- Pool, AC, Sauna, Gym, Tennis!

Cozy 2 bedroom true log cabin

Charming Sugarbush Standalone Condo
Weekly house rentals

Home Base in the Heart of the Adirondacks

Camp Wildwood

Lake Champlain and the Adirondack Mountains!

Bittersweet Retreat on Willsboro Point

Adirondacks 46 peaks LakeChamplain Retreat

Quiet Adirondack Retreat with MASSIVE Views

Magical Augur Lake Retreat-Great for Large Groups!

Highlands Landing -Lakeside Getaway!
Private house rentals

The Lake House Retreat

Owl's Head Overlook

Iron Peaks Lodge- Near Whiteface, dogs welcome!

Hidden gem, 2BR-2 Living, in a quiet neighborhood

Historic Edge of the River, Adirondacks

The Looking Glass, a modernistic escape

The Gambrel Mountain Retreat at Twin Ponds

ADK Lake Champlain Retreat
Destinations to explore
- New York City Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Québec City Holiday rentals
- Niagara Falls Holiday rentals
- Newark Holiday rentals
- Jersey City Holiday rentals
- Portland Holiday rentals
- Mont-Tremblant Holiday rentals
- Providence Holiday rentals
- Newport Holiday rentals
- Buffalo Holiday rentals
- Family-friendly rentals Chesterfield
- Rentals with a fireplace Chesterfield
- Rentals with a kayak Chesterfield
- Rentals with a firepit Chesterfield
- Rentals with beach access Chesterfield
- Rentals with a patio Chesterfield
- Rentals with outdoor seating Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Rentals with lake access Chesterfield
- Waterfront rentals Chesterfield
- Pet-friendly rentals Chesterfield
- House rentals Essex County
- House rentals New York
- House rentals United States
- Sugarbush Resort
- Bolton Valley Resort
- Stowe Mountain Resort
- Fort Ticonderoga
- Whiteface Mountain Ski Resort
- University of Vermont
- Middlebury College
- Lake Flower
- Parc Safari
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- ECHO, Leahy Center for Lake Champlain
- Snow Farm Vineyard & Winery
- Shelburne Vineyard
- Warren Falls
- Shelburne Museum
- Elmore State Park
- Cold Hollow Cider Mill
- Waterfront Park
- Boyden Valley Winery & Spirits
- Cochran's Ski Area
- Lake Champlain Chocolates
- Ethan Allen Homestead Museum
- Titus Mountain Family Ski Center
- Green River Reservoir State Park





