
Vacation rentals in Chesterfield
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Top-rated vacation rentals in Chesterfield
Guests agree: these stays 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.

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.

"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!

Cottontail Cottage - Snowshoes, Fireplace & Sauna
Quiet and peaceful cottage in a beautiful setting. Located on 6 acres adjacent to the Shelburne Pond Nature Reserve and only 15 min to the Church Street Marketplace in downtown Burlington. Enjoy the sunrise over the hills behind the cottage and sunsets over the Adirondacks to the west. Sit in the chairs or chaise lounge in the private backyard listening to the birds or relax in the shared sauna after a day of skiing or snowshoeing. (The sauna is available by reservation to ensure your privacy.)

Moon Ridge Cabin *Hottub*
Our cabin is a studio with a hot tub & all the amenities. A queen bed, linens, towels, small refrigerator/freezer, microwave, single burner cook plate, dishes, utensils, glassware, pots & pans, toaster & coffee maker. Roku Tv & dvd player with movies. The cabin's bathroom is simular to a cruise ship, you step up into your shower. There is also an private outdoor shower. There is a fire pit with an attached grill & hibachi. We have a garden area & privacy fence between our home & the cabin.

Cozy Rustic Apartment
We are located on the famous Ausable River within a 30 minute drive to many of the High Peak trails, the beautiful Ausable Chasm, and Whiteface mountain. We are 5 miles from Interstate 87. The apartment can be a cozy retreat after spending a day exploring in the Adirondacks. Spend time strolling down to the river to enjoy the scenic views or enjoy quality downtime with family. The apartment has a unique style of its own that will provide you a comfortable and reasonable price place to stay.

The Shepherd's Crook at Blue Pepper Farm
Tucked in the woods on our working sheep farm, our off-grid tiny house is the perfect escape and stepping stone into the Adirondack mountains for hiking, skiing, and snowshoeing. Enjoy the coziness of the Crook between forays into our north country wilderness! What you will find: adventure, peace, quiet, woodstove, candles, down blanket, fire pit, privacy, composting outhouse, firewood for sale. **Please note there is NO electricity and NO running water. Akin to glamping!

"Gateway To The Adirondacks" on Main Street
Situated in the heart of the village on Main Street in Au Sable Forks, the "Gateway to the Adirondacks", you'll find this newly renovated second floor apartment. This spacious unit offers a fully equipped kitchen, two bedrooms, full bath and comfortably furnished living room with Smart TV and WiFi. Conveniently located within walking distance to grocery stores, pub, eateries, and entertainment. Enjoy fishing, biking, hiking, Whiteface Mountain and Lake Placid.

Winter Wonderland w/ hot tub perfect for couples
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.

Modern Tiny House
Charming oasis in the quaint Village of AuSable Forks centrally located 30 mins either to Lake Placid or Plattsburgh NY. Located 20 mins from Whiteface Mountain/15 mins to AuSable Chasm. Walking distance to town including deli, pizza place, grocery store, local pub and of course fishing on the AuSable River. Short drive to tons of hiking, boating, mountain biking and skiing and all that the Adirondacks has to offer.

Cozy Cabin
Cabin located across from Macomb State Park providing access to cross country skiing. 30 minute drive to Whiteface Mt. Ski Area. Sleeps 4 with 2 twins and a double in upstairs loft. Fully furnished kitchen, bath with shower. Quiet space. No smoking indoors. No cats. Dogs allowed but must be well behaved and stay off of the furniture and bedding. Check-in @ 3 PM and beyond. Checkout at 11 AM.
Popular amenities for Chesterfield vacation rentals
Other great vacation rentals in Chesterfield

Plattsburgh NY area 15 min to CVPH Hospital

Light-Filled Studio Near Burlington w/ Balcony

Bittersweet Retreat on Willsboro Point

Quiet Adirondack Retreat with MASSIVE Views

Rustic ADK Mountain tiny Cabin -partial off grid

Historic Edge of the River, Adirondacks

Studio Se7en by Burlington

Adirondack Getaway Minutes from Whiteface/Ironman
Frequently Asked Questions
What are the most popular amenities for Cabin Rentals in Chesterfield?
Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in house rentals in Chesterfield?
Experience the best of Chesterfield with our house rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cabin rentals in Chesterfield have wifi?
Absolutely! We offer over 10 cabin rentals with wifi in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Chesterfield?
Four-legged friends are welcome in Chesterfield. Choose from more than 40 vacation rentals for guests traveling with pets.
Do cabin rentals in Chesterfield have free parking?
Absolutely! We offer over 10 cabin rentals with free parking in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Chesterfield?
Yes! Work meets play with ease at over 30 vacation rentals in Chesterfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly vacation rentals in Chesterfield?
Chesterfield has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Chesterfield have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in Chesterfield

Total vacation rentals
Explore 90 vacation rentals in Chesterfield

Nightly prices starting at
Chesterfield vacation rentals start at ﺩ.ﺇ294 per night before taxes and fees

Verified guest reviews
Over 4,890 verified reviews to help you choose

Family-friendly vacation rentals
60 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
80 of Chesterfield vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chesterfield rentals

4.9 Average rating
Chesterfield stays are highly rated by guests—averaging 4.9 out of 5!
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- House rentals Chesterfield
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- Sugarbush Resort
- Parc Safari
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Autumn Mountain Winery
- Country Club of Vermont
- Burlington Country Club
- Ethan Allen Homestead Museum
- ECHO, Leahy Center for Lake Champlain
- Vermont National Country Club
- Lincoln Peak Vineyard
- Titus Mountain Family Ski Center
- Shelburne Vineyard
- Snow Farm Vineyard & Winery
- Boyden Valley Winery & Spirits
- North Branch Vineyards




