
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.

Cozy Mountain House- 50 acres/Trails/Whiteface mnt
Private pet friendly house, w/ 2 bedrooms, 1 bath, full kitchen and 2 living rooms. Down stairs living room is a private space w/ queen sofa bed and cozy fireplace. Located on 50+ acres in the heart of the ADK mountains, 6 mins from Whiteface Ski Resort and 20 min from Lake Placid. Hiking, mnt biking and cross-country ski trails out your front door. Open deck w/ beautiful views, opportunity to see wildlife and amazing star gazing on clear nights. Perfect for couples, small groups and families.

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!

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.

Secluded Log Cabin with Unrivaled Views!
Luxurious log cabin on the edge of the Green Forest National Park. The house is set in a peaceful and quiet location overlooking many miles of Vermont mountains. Ideal for families and those seeking peace and solitude. Hiking and cycling trails at doorstep. 10min drive to local town of Hancock and a further 10min drive to Rochester. Wild turkeys often seen wandering across the front lawn. Wild deer and moose are in the woods. Ruby throated humming birds come to feed at the kitchen window.

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.

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.

Lake Front Home in Plattsburgh - 4BR Sleeps 11!
Escape to our Lake Champlain haven! Unwind on your private rocky beach, soak in stunning lake and mountain views, and relax in our spacious, sun-filled home. Perfect for family and friends, our prime location offers easy access to local gems. Enjoy nearby City beach and Point au Roche beach. Just 10 minutes from Champlain Centre Mall for shopping. Experience lakeside living with modern comforts. Book now for an unforgettable getaway on Lake Champlain's shores!

Mountain Valley Retreat
This newly renovated home offers a comfortable home away from home. Enjoy an Adirondack experience at this centrally-located retreat just 10 minutes from White Mountain Ski area, 20 minutes from Lake Placid, and 15 minutes to Keene Valley. Conveniently located near many hiking, biking and cross-country ski trails. Enjoy the gazebo with new hot tub, and fire pit surrounded by Adirondack chairs. Come stay and enjoy all the Adirondacks has to offer.

Forest Hideaway
Our single story 2 bedroom 1 bath home is located within 30 minutes of Mad River Glen and Sugarbush ski areas and the quaint towns of Bristol, Richmond and Waitsfield. Drive another 15 minutes to Burlington or the Bolton Valley Ski Area. Hiking, biking and cross country skiing trails nearby, or just sit on the porch and enjoy the sounds of the nearby river. Snow tires and front wheel or 4 wheel drive vehicles necessary during the winter months.

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.

Sauna, Dock & 180° Views – Lakefront Retreat
Tucked on a private peninsula with 180°+ of lakefront views, our 3-bedroom retreat invites you to relax, recharge, and reconnect. Paddle from your private dock, sweat in the lakeside sauna, or sip coffee on the deck as the sun rises over Lake Iroquois. Thoughtfully designed with cozy nooks, modern comforts, and optional healing experiences, this is Vermont soul-care at its finest—just 25 minutes from Burlington.
Popular amenities for Chesterfield house rentals
House rentals with a pool

Modern, Trendy Townhome in Stowe! Newly Remodeled

Mott House, South Hero Vermont

Lakeside Bungalow ~ Pool | Hot Tub | Beach

Charming Sugarbush Standalone Condo

Stunning Mountain Top Cabin

Private 3 Acre Forest Retreat 3 Min to Stowe Mtn

Catherine House

Concrete Ski House Near Sugarbush
Weekly house rentals

Camp Wildwood

Renovated East Middlebury House

Lake Champlain-ADK Mountains, Winter Specials!

Adirondacks 46 peaks LakeChamplain retreat

Snowy Meadow Getaway—Ski Smugglers, Stowe, JayPeak

Mallets Bay Ranch

Vermont Lakeside Cottage

Magical Augur Lake Retreat-Great for Large Groups!
Private house rentals

The Kennedy House BTV, UVM

“Rosie's”

Historic Edge of the River, Adirondacks

Spacious new home on 225 Acres! Unit 2

Spectacular views at the “Edge” of Lake Champlain

Relax on the Shores of Lake Champlain

ADK Lake Champlain Retreat

Gorgeous Lakefront Home w/ Private Beach & Views
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Pocono Mountains Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Rentals with lake access Chesterfield
- Waterfront rentals Chesterfield
- Rentals with a fire pit Chesterfield
- Rentals with outdoor seating Chesterfield
- Rentals with a patio Chesterfield
- Rentals with a fireplace Chesterfield
- Rentals with a kayak Chesterfield
- Pet-friendly rentals Chesterfield
- Family-friendly rentals Chesterfield
- Rentals with beach access Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- House rentals Essex County
- House rentals New York
- House rentals United States
- Sugarbush Resort
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Lake Flower
- Stowe Mountain Resort
- ECHO, Leahy Center for Lake Champlain
- University of Vermont
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- Adirondak Loj
- Shelburne Museum
- Middlebury College
- Boyden Valley Winery & Spirits
- Shelburne Vineyard
- Warren Falls
- Waterfront Park
- Lake Champlain Chocolates
- Snow Farm Vineyard & Winery
- Elmore State Park
- Cold Hollow Cider Mill




