
House holiday rentals in Chesterfield
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Top-rated house rentals in Chesterfield
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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!

Entire House. 2+ bed, 2 bath near Lake & bikeway
Kick back and relax in this stylish space located less than 3 miles to downtown and under a mile walk to lake vistas & beaches. Access to the bike path is at the end of the street. Perfect for cyclists, runners, bikers, dog walkers & beach goers. Completely remodeled house with new appliances, fully equipped kitchen, laundry & high speed internet. Two bedroom suites each with their own bathroom; the King suite upstairs has additional TV & sitting area. Plus there is a bonus room with futon.

Modern, hilltop, lakeside retreat!
Escape to a modern winter retreat nestled among towering trees with stunning views of Mallets Bay. This cozy, luxurious haven, built in 2021, is perfect for gathering with loved ones or a peaceful getaway. Just 15 minutes from Burlington and Winooski, enjoy nearby dining, unique shops & winter adventures. End your day around the Solo Stove for a cozy fire, sharing stories and laughter under the stars. Start each morning with lake views & local coffee—our serene space is the ideal winter escape!

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.

The Quiet Cul-de-Sac BTV, UVM
Enjoy your stay in our well maintained home located at the end of a quiet cul de sac with a fenced in private backyard. Two minute drive/five minute walk to the airport. Less than a 10 minute drive to Interstate 89, University of Vermont, the UVMMC Hospital and downtown Burlington. Approximately a 30 minute drive to many of Vermont’s attractions such as skiing (45 minutes to Stowe), wine tasting, apple orchards, Lake Champlain and Maple Sugar sites. On site driveway for parking two vehicles.

New Modern Home w/ Parking Soaking Tub, EV Charger
Located a 5 minute walk from downtown Burlington and boasting a secluded and private rooftop terrace for guests exclusive use, you'll enjoy stunning views of Burlington's historic Old North End in a relaxing and private atmosphere. Custom modern home has all new appliances, fully equipped kitchen, deep soaking tub, and washer/dryer. This will truly be your perfect home away from home. 2 private off street parking spaces are included with a dedicated EV charger for you during their stay.

The Blue Jay Aframe
Get lost at the @thebluejayframe (find us on the gram)! This beautiful Aframe has been completely renovated (BRAND NEW) to make your stay in the Adirondacks a special one! The Aframe sits nestled in the Ausable Acres where you're a short driving distance to Wilmington, Lake Placid, and Keene Valley. An ideal place to visit for a couple/family looking for a private getaway experience feeling the fresh air of the ADKS's while still having modern comfort. Cozy! Modern! Relaxing! ENJOY!!

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.

Stunning remodel walking to Lake Champlain
Absolutely beautiful remodeled duplex in amazing Burlington neighborhood , walking distance to Lake Champlain, Pine Street and the Hula Work space. This four bedroom 2.5 bathroom is a perfect oasis. One King bedroom, a queen, a queen Murphy bed that is in it's own private bedroom and can be converted to an office and a bunk room. Hot tub with views of Lake Champlain. Downstairs living room with large tv, then upstairs, den area with another TV,bar and views of Lake Champlain

Cozy "Urban" Cottage
Welcome to my super cozy house in the Old North End! The house is a 15 minute walk to the top of Church Street and is located near a market, yoga studio, and coffee shop. There is a farmer's market located directly across the street on Tuesday afternoons in the summer months. The house has tons of natural light, a comfy sofa and mattresses, a large TV with access to Netflix and HBO, and lots of books. Both bedrooms have sound machines and fans. Coffee and tea provided!
Popular amenities for Chesterfield house rentals
House rentals with a pool

Sunset Treehouse

Epic Views of the Green Mountains

Cozy Mountain Home at Sugarbush!

Mott House, South Hero Vermont

Lakeside Bungalow ~ Pool | Hot Tub | Beach

Charming Sugarbush Standalone Condo

Catherine House

Concrete Ski House Near Sugarbush
Weekly house rentals

Escape to the Adirondack

*Private 3 Bedroom near lake, bike path, park

Lake Champlain-ADK Mountains, Winter Specials!

Quiet Adirondack Retreat with MASSIVE Views

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

Jay Ski Base

Modern, clean and cozy in top location

Modern House on Lake Champlain
Private house rentals

Bright, modern home perfect for friends and family

Artsy Bungalow

Camp Wildwood

Backyard Bungalow • 2BR Near BTV + Fenced Yard

Historic Edge of the River, Adirondacks

Lakeview Cottage

Modernist Cabin with mountain views, Bauschaus VT

ADK Cottage with Mountain Views
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal 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
- Rentals with a fireplace Chesterfield
- Rentals with a kayak Chesterfield
- Rentals with a fire pit Chesterfield
- Waterfront rentals Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Rentals with outdoor seating Chesterfield
- Rentals with beach access Chesterfield
- Family-friendly rentals Chesterfield
- Rentals with a patio 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
- Whiteface Mountain Ski Resort
- Lake Flower
- Fort Ticonderoga
- University of Vermont
- ECHO, Leahy Center for Lake Champlain
- Middlebury College
- Shelburne Vineyard
- Snow Farm Vineyard & Winery
- Boyden Valley Winery & Spirits
- Adirondak Loj
- Waterfront Park
- Lake Champlain Chocolates
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- Shelburne Museum
- Warren Falls
- Cold Hollow Cider Mill
- Elmore State Park




