
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.

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.

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.

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.

Secluded Chalet w/ Hottub & Stunning Mtn Views
Welcome to our cozy secluded Jay Peaks Chalet! Tucked away on 11 acres of natural beauty, this charming home is just a 15-minute drive from White Face Mountain, making it the ideal starting point for your mountain adventures or relaxation. Cozy bedrooms with forest views, a private hot tub, Firepit, screened in porch, and plenty of privacy. Book now for an unforgettable escape for the entire family. Your dogs will love it too!
Popular amenities for Chesterfield house rentals
House rentals with a pool

Last Run Stowe: Pool, spacious, 5min to Village

Mott House, South Hero Vermont

Lakeside Bungalow ~ Pool | Hot Tub | Beach

Cozy 2 bedroom true log cabin

Charming Sugarbush Standalone Condo

Stunning Mountain Top Cabin

Private 3 Acre Forest Retreat | Trails Pool Fire

Sugar House Homestead: A Perfect Retreat
Weekly house rentals

The Lake House Retreat

Home Base in the Heart of the Adirondacks

Historic Edge of the River, Adirondacks

The Looking Glass, a modernistic escape

The Gambrel Mountain Retreat at Twin Ponds

Mountain View

Spectacular views at the “Edge” of Lake Champlain

Shelburne Bay Waterfront Getaway
Private house rentals

Adirondack A-frame 4bd-2ba: Ski/Hike/Bike & More

Owl's Head Overlook

Iron Peaks Lodge- Near Whiteface, dogs welcome!

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

The Lake House – Lake Champlain Waterfront Retreat

Lakeside Villa

The H Cottage - free mooring - beach access

M&T AirBnB
Destinations to explore
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- Rentals with a fireplace Chesterfield
- Rentals with a kayak Chesterfield
- Rentals with a patio Chesterfield
- Family-friendly rentals Chesterfield
- Waterfront rentals Chesterfield
- Rentals with a fire pit Chesterfield
- Rentals with beach access Chesterfield
- Rentals with outdoor seating Chesterfield
- Pet-friendly rentals Chesterfield
- Rentals with a washer and dryer Chesterfield
- Rentals with lake access Chesterfield
- House rentals Essex County
- House rentals New York
- House rentals United States
- Sugarbush Resort
- Stowe Mountain Resort
- Bolton Valley Resort
- Fort Ticonderoga
- Lake Flower
- Whiteface Mountain Ski Resort
- Parc Safari
- Middlebury College
- ECHO, Leahy Center for Lake Champlain
- University of Vermont
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- Warren Falls
- Shelburne Museum
- Elmore State Park
- Snow Farm Vineyard & Winery
- Shelburne Vineyard
- Cold Hollow Cider Mill
- Waterfront Park
- Cochran's Ski Area
- Lake Champlain Chocolates
- Boyden Valley Winery & Spirits
- Ethan Allen Homestead Museum
- Titus Mountain Family Ski Center
- Lincoln Peak Vineyard





