$4,500
Available: Right Now
Listed: 26/04/2024
Chester, VT, 05143
Overview Our historic 1868 'Elm House' is located in the picturesque town of Chester, nestled in the heart of Chester Depot. The 'Elm House' is perfect for city dwellers looking for a country escape, traveling families, romantic getaways, ...
$13,920
Available: Right Now
Listed: 26/04/2024
Chester, VT, 05143
Great Central Vermont location! Private but easy to get too. Ten miles to Okemo/Jackson Gore. Skiing, golfing, hiking, snowmobiling, Mountain biking, cross country skiing, snowshoeing. Forty minutes to Manchester, Woodstock & Dartmouth. Great for cou...
$15,030
Available: Right Now
Listed: 19/04/2024
Chester, VT, 05143
Maple Leaf Manor provides its guests with a comfortable stay in a renovated 1864 Brick Federal Style Farmhouse on 8 acres, as well as a true Southern Vermont experience in the heart of Chester, Vermont. Nestled on lovely grounds, this home is sur...
$15,000
Available: Right Now
Listed: 22/04/2024
Chester, VT, 05143
Centrally located home for all of your year-round outdoor activities! Come enjoy all Vermont has to offer on this 3-acre property. Great skiing, golf, and VAST trails are all nearby as well as hiking and kayaking at nearby Lowell Lake. Cozy up by the...
$9,000
Available: Right Now
Listed: 22/04/2024
Chester, VT, 05143
This charming cabin offers 3 bedrooms, 2 full baths, a spacious living room area with wood burning stove, Finished basement / bunk room with 6 Twin Beds and Large flat screen TV and is a great property for sledding, snow shoeing, hiking, etc. The tow...
$11,940
Available: Right Now
Listed: 26/04/2024
Chester, VT, 05143
This incredible log home is the perfect spot for a weekend getaway or an extended stay in Vermont. Nestled on 6 acres of beautiful mountain-view land, this 4 bedroom home gives you all the amenities you need and more. Wake up each morning to the fres...
$25,500
Available: Right Now
Listed: 26/04/2024
Chester, VT, 05143
Come up solo or bring friends and family to our unique and lovingly renovated estate! Our charming 1860’s farmhouse sleeps up to 12 (with room for more) and features over two acres of terraced gardens and two historic barns on a 10 acre property....
$19,140
Available: Right Now
Listed: 26/04/2024
Chester, VT, 05143
Lovingly updated antique 6 bedroom home in the historic Stone Village of Chester, VT. Sleeps 10 comfortably making it the perfect vacation home for 1 or 2 families. Main stone house was built in 1833 as an addition to the 1798 farmhouse. Combined...
$8,430
Available: Right Now
Listed: 26/04/2024
Chester, VT, 05143
Welcome to 'Smokeshire Hilltop Farmhouse!' This lovely 5-bedroom, 2-bathroom vacation rental sits on a plateau above the Williams River in Chester. Located on a working farm with beautiful grounds, the rustic farmhouse offers travels the ideal escape...
$12,090
Available: Right Now
Listed: 26/04/2024
Chester, VT, 05143
Gather with family and friends at our spacious home nestled in the Vermont woods.The Blue Moon Bungalow is your home away from home, with everything you need for a relaxing getaway, with the beauty of nature all around. Our large, open floor plan...
$7,860
Available: Right Now
Listed: 24/04/2024
Chester, VT, 05143
Okemo Valley ChaletOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Discover the year-round beauty, endless recreation options, and historic hamlets of the...
$10,140
Available: Right Now
Listed: 26/04/2024
Chester, VT, 05143
Rest, relax, and enjoy the tranquil surroundings when you visit this vacation rental home in Chester, Vermont! The stunning house has 4 bedrooms, 3 bathrooms, and boasts exposed beams, wall-to-wall windows, and vaulted ceilings. Complete with an imma...
$14,220
Available: Right Now
Listed: 23/04/2024
Chester, VT, 05143
Enjoy a historic stay in this former Chester Schoolhouse recently renovated into a massive yet cozy home. Located only 13 min away from Okemo Mountain and central to restaurants, shopping, hiking, and recreational activities. This unique property has...
$12,000
Available: Right Now
Listed: 25/04/2024
Chester, VT, 05143
We got the snow !Perfectly situated between Stratton (15mi), Okemo (15mi), Bromley (12mi) and Magic Mountain (2mi) resorts, The Octagon at Powder Mill is a perfect getaway for skiers and adventurers looking for winter outdoor activities, a...
$5,400
Available: Right Now
Listed: 18/04/2024
Chester, VT, 05143
Welcome to this charming farmhouse on a peaceful residential street close to the heart of Chester.This home has comfortable living spaces, sizable bedrooms, and a fantastic kitchen to cook in––all combined with a thoughtful Vermont and mid-centur...