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

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.

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.

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!

Artsy Bungalow
This newly renovated artsy bungalow offers a convenient, peaceful and stylish place to stay while exploring the Burlington/Winooski area. The 3 bed 1 3/4 bath home is nestled on a quiet street in vibrant Winooski. The home is a 10 minute drive to downtown Burlington & the airport, and a short walk to the river, several cafes, restaurants, pubs, and a brewery. Winooski is referred to as “the Brooklyn of Burlington” because of the foodie scene and rich cultural diversity.

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.

Saranac River Trail in the Adirondacks
Located along the beautiful Saranac River in North Eastern NY, 5 minutes from SUNY Plattsburgh,10 minutes from Lake Champlain, 50 minutes from Lake Placid, 1 hour from Montreal and 1 hour from Burlington VT. White Face Mountain, skiing, snowboarding, cross country skiing, ADK 46 High Peaks, hiking, golfing, and fishing are all a short drive away. Plattsburgh NY with its amazing restaurants and bar scene is a 5-minute drive. Plenty of parking space.

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.
Popular amenities for house rentals in Chesterfield
House rentals with a pool

Sunset Treehouse

Epic Views of the Green Mountains

Mott House, South Hero Vermont

Lakeside Bungalow ~ Pool | Hot Tub | Beach

Charming Sugarbush Standalone Condo

Stunning Mountain Top Cabin

Catherine House

EPIC Stowe Getaway - Great For Families & Friends
Weekly house rentals

Escape to the Adirondack

Quiet Adirondack Retreat with MASSIVE Views

Adirondacks 46 peaks LakeChamplain retreat

Jay Ski Base

Nice one bedroom cottage

Jay Brook Lodge near Whiteface

Second story stay

Enjoy every season in the Lake Champlain Region
Private house rentals

Camp Wildwood

*Private 3 Bedroom near lake, bike path, park

Lake Champlain-ADK Mountains, Winter Specials!

Chalet 86 - Minutes from Whiteface & Hiking

Lake Champlain Ski/Lake House

Simplistic Elegance.

Modern House on Lake Champlain

Adirondack winter vibes! Book now.
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 a firepit Chesterfield
- Rentals with a patio Chesterfield
- Rentals with a fireplace Chesterfield
- Rentals with a kayak Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Rentals with lake access Chesterfield
- Waterfront rentals Chesterfield
- Rentals with beach access Chesterfield
- Rentals with outdoor seating Chesterfield
- Pet-friendly rentals Chesterfield
- Family-friendly rentals Chesterfield
- House rentals Essex County
- House rentals New York
- House rentals United States
- Sugarbush Resort
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Lake Flower
- Fort Ticonderoga
- ECHO, Leahy Center for Lake Champlain
- Middlebury College
- Boyden Valley Winery & Spirits
- Snow Farm Vineyard & Winery
- Adirondak Loj
- Shelburne Vineyard
- Stowe Mountain Resort
- Shelburne Museum
- University of Vermont
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- Warren Falls
- Waterfront Park
- Elmore State Park
- Cold Hollow Cider Mill
- Lake Champlain Chocolates




