
Holiday rentals in Chesterfield
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Chesterfield
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

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!

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.

Quiet Adirondack Retreat with MASSIVE Views
Come rejuvenate at our Adirondack hilltop home on 7 acres overlooking Lake Champlain, Green Mountains of Vermont, and the Adirondack Park. **30 minutes from Whiteface Mountain skiing** Whether you are looking to reconnect with family/friends, unwind after a day of hiking/biking/skiing/golfing/leaf peeping in the Adirondacks or finish that book/album you are working on, you will find a quiet environment to relax and enjoy your break inside the Blue Line of the 6-million-acre Adirondack Park.

Magical Augur Lake Retreat-Great for Large Groups!
Perched on 2 acres overlooking Augur Lake, bring the whole family to experience the magic of this amazing place with lots of room for fun playing in the sandbox, lawn games, paddling, and bonfires; or enjoy some relaxation and watch the sunrise on the lake from the patio with a cup of coffee or take in the fresh evening breeze during happy hour. Whether you decide to cozy up by the fireplace with your favorite book, or are playing board games, the memories you make here will last a lifetime.

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.

Modern House on Lake Champlain
Unplug and unwind in this renovated mid-century-modern inspired house on Lake Champlain in the Adirondack Park. Enjoy privacy and nature on the 3.5 acre lot with 200 feet of shore. The bedrooms each have en-suite bathrooms. Relax in the soaking tub and watch a movie. Sink into an Adirondack chair, take in Mount Mansfield and be on the lookout for deer and other wildlife. Take a short hike through a cedar forest down to the shore. The house also serves as an art gallery for local artists.

Adirondack Cabin Retreat – Hot Tub + Lake
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. Lastly for security, we have a camera focused on driveway entrance.

High Peaks Haven
Welcome to High Peaks Haven. Big House, Long Driveway right off the throughway Nestled in the beauty of High Peaks region. Our retreat blends comfort, style, and convenience for the perfect getaway. From May through December enjoy hot tub in the gazebo the ideal spot to unwind under the stars after a day of adventure with family and or friends. Perfect for getaways or work stays, this spacious home offers privacy, plenty of parking, and modern comforts including an EV Level 2 Charger.

The Farmhouse
Nestled in the rolling hills of the Adirondack Mountains, 'The Farmhouse' is a guest house attached to our home and provides a serene setting for you and your family. Hiking, camping, and woodland walks abound in the area, including a newly established trail less than 0.1 miles from the front door. Nearby Lake Champlain provides endless water oppourtunites, and Whiteface mountain, a 45 minute drive is a major ski and hiking destination. Ausable Chasm is a short 15 minutes away.

Autumn Forest Retreat | Hot Tub + Massage Chair
⭐ TOP 1% STAY — 300+ 5★ Reviews Guests often say: “This was exactly what we needed.” Welcome to Place of Prana — a peaceful Adirondack escape designed for rest, healing, and true reset. Summer weekends are filling quickly ☀️ Book your Adirondack escape before the season is gone. Are your dates unavailable? Explore our sister stay, Place of Poiema — another peaceful Adirondack retreat designed for gathering, connection, and unforgettable time together for 10 guests.
Popular amenities for Chesterfield holiday rentals
Stay near Chesterfield's top sights
Other great holiday rentals in Chesterfield

Willsboro Point Waterfront Retreat

Highlands Landing -Lakeside Getaway with Sauna!

Camp Wildwood

Stunning Lakefront Paradise

Addirondack Art Home - Best Lake view

The Mountain waits

Willow Hill Farm

Modern 2 BR Apt in Essex NY on Lake Champlain
Destinations to explore
- 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
- Snow Farm Vineyard & Winery
- Warren Falls
- Shelburne Vineyard
- Shelburne Museum
- Cold Hollow Cider Mill
- Elmore State Park
- Waterfront Park
- Boyden Valley Winery & Spirits
- Lake Champlain Chocolates
- Green River Reservoir State Park
- Branbury State Park
- Titus Mountain Family Ski Center
- Ethan Allen Homestead Museum
- Little River State Park
- Alburg Dunes State Park
- Parc Safari





