$6,000
Available: Right Now
Listed: 04/06/2024
Chester, VT, 05143
About this spaceWake up to brisk mountain air with a cup of coffee and moose in the front yard... This house is a sanctuary, ideal for ski trips, hiking, leaf peeping, wine, beer, and cheese tasting, shopping and sugar house adventures.This i...
$7,680
Available: Right Now
Listed: 05/06/2024
Chester, VT, 05143
Discover the perfect escape in the heart of a charming ski town. Our cozy and rustic home offers a peaceful retreat where you can unwind and enjoy all the attractions this town has to offer. Nestled amidst the trees, this inviting house provides a co...
$7,350
Available: Right Now
Listed: 04/06/2024
Chester, VT, 05143
Welcome to our cozy log home nestled on 6 acres of picturesque Vermont countryside. If you're seeking a peaceful and rejuvenating getaway, look no further.Step inside, you'll be greeted by the warm and inviting atmosphere. The open concept living...
$8,310
Available: Right Now
Listed: 05/06/2024
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...
$8,190
Available: Right Now
Listed: 05/06/2024
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...
$6,330
Available: Right Now
Listed: 04/06/2024
Chester, VT, 05143
Welcome to Sage House at Camp Greenwood: a brand new micro tiny house village central to the best attractions in Southern Vermont! Skiing, hiking, dining....and a barrel sauna and private pond available to our guests! As featured on A&E's Living Smal...
$13,500
Available: Right Now
Listed: 04/06/2024
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...
$5,970
Available: Right Now
Listed: 04/06/2024
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, ...
$15,000
Available: Right Now
Listed: 04/06/2024
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...
$8,100
Available: Right Now
Listed: 04/06/2024
Chester, VT, 05143
Relax on the patio on the bank of the Williams River to watch the leaves turn, explore hiking trails, enjoy the outdoor fire pit, and mnt bike. Play soccer on indoor turf or corn hole in the rec room—half mi. from outdoor ice skating, disk golf, andV...
$8,070
Available: Right Now
Listed: 05/06/2024
Chester, VT, 05143
Ideal to host up to 7 guests, this home on 2 acres of land is a perfect retreat for anyone looking to be in the heart of nature. Chester and Ludlow, VT are minutes away and call you to explore historic landmarks and enjoy skiing at Okemo Mountain (lo...
$6,270
Available: Right Now
Listed: 05/06/2024
Chester, VT, 05143
Sunshine, flowers, Farmers' Markets, hikes and starry nights are here. Scents fill the air and the birds are calling. Dining outdoors begins and music groups perform on the green. Bucolic and tranquil, Vermont calls.If hiking is not on the schedu...
$3,930
Available: Right Now
Listed: 06/06/2024
Chester, VT, 05143
This is our very cozy 1850 home in the Stone Village of Chester. The house has many of the original features and charm including wide plank pine flooring, plaster walls and original molding. Some of the door hardware is very unique and original to pr...
$4,980
Available: Right Now
Listed: 05/06/2024
Chester, VT, 05143
Welcome to Zen of the Woods! A cozy, thoughtfully designed tiny cabin retreat minutes from Okemo. Set amongst hundreds of acres of forest and farmland, find peace as you enjoy your morning coffee on the front porch overlooking the landscape. Take a w...
$3,750
Available: Right Now
Listed: 04/06/2024
Chester, VT, 05143
Adorable Cozy Cottage - sits on a mountainside with an OMG view- ideal for Cyclist, Skiers, Fall Leaf Peakers, Summer get away. 10 minutes from Historic Weston, 10-40minutes from 4 major ski areas, Magic, Okemo, Bromley and Stratton. Sleigh rides and...
$14,370
Available: Right Now
Listed: 06/06/2024
Chester, VT, 05143
Nestled in the heart of the majestic Green Mountains, this charming 4-season retreat offers 12-acres of stunning views, modern comforts, and a peaceful atmosphere. Our cabin is ideal for families, couples, or anyone looking to unwind in nature.Ad...
$6,000
Available: Right Now
Listed: 04/06/2024
Chester, VT, 05143
Enjoy a private room & bathroom with tub in the historic Chester Inn, circa 1780. This charming property is conveniently located on Main St in walking distance to restaurants, shops & galleries.Public hiking/snowshoeing trails can be entered righ...
$9,270
Available: Right Now
Listed: 05/06/2024
Chester, VT, 05143
Beautiful hilltop cabin on 25 private acres bordering the William's River State Forest. Relax at this private retreat or visit many of the nearby state parks, mountain resorts, and other attractions. (Okemo 20 miles, Bromley 17 miles, Stratton 21 mil...
$6,180
Available: Right Now
Listed: 05/06/2024
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...
$7,020
Available: Right Now
Listed: 04/06/2024
Chester, VT, 05143
-ListingThe perfect home for your next Vermont getaway! Rustic, spacious, and peaceful home with plenty to do in the beautiful Green Mountains of Vermont. Located in the quaint town of Chester (One of the oldest and most historical towns in the s...
$14,010
Available: Right Now
Listed: 05/06/2024
Chester, VT, 05143
Weekly and longer rentals for Summer. 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. Nestl...
$14,220
Available: Right Now
Listed: 04/06/2024
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...