$7,500
Available: Right Now
Listed: 28/04/2024
Chester, VT, 05143
Sportsman themed, real log cabin that has comfortable wood stove & hearth, plus backup regular heat. Bathroom with shower for two and upstairs standable loft with a queen and full double bed. Upstairs & downstairs HD SmartTV/DVDplayer setups, plus in...
$6,000
Available: Right Now
Listed: 28/04/2024
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...
$11,940
Available: Right Now
Listed: 01/05/2024
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...
$2,550
Available: Right Now
Listed: 28/04/2024
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...
$3,300
Available: Right Now
Listed: 28/04/2024
Chester, VT, 05143
This is a mostly off grid cabin with total privacy. Quiet yet just 2 miles off Rt 103. If you are looking for a place to escape the world, or a home base from which to explore this corner of Vermont our 4 season, newly built cabin is for you! Full Ki...
$7,740
Available: Right Now
Listed: 28/04/2024
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...
$7,020
Available: Right Now
Listed: 24/04/2024
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...
$3,840
Available: Right Now
Listed: 01/05/2024
Chester, VT, 05143
Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and taverns, antique shops, art galleries and a country market.Explore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers ...
$7,350
Available: Right Now
Listed: 29/04/2024
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...
$8,100
Available: Right Now
Listed: 27/04/2024
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...
$14,400
Available: Right Now
Listed: 28/04/2024
Chester, VT, 05143
Ski Okemo? CheckSledding in the back yard? CheckIce Skating on your own pond? CheckSnowshoeing in your own trails? CheckSnowmobiling? CheckHot Tub? CheckEnjoy lovely views of the mountains, overlooking our skating pond, and ex...
$15,240
Available: Right Now
Listed: 29/04/2024
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...
$8,970
Available: Right Now
Listed: 28/04/2024
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...
$9,000
Available: Right Now
Listed: 30/04/2024
Chester, VT, 05143
You will enjoy Vermont at this beautifully renovated house set on 12 acres in the quaint town of Chester. You can relax by the cozy pellet stove and enjoy the view, or have a movie night upstairs in the loft area. The house is just a quick drive to M...
$19,140
Available: Right Now
Listed: 01/05/2024
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...
$12,090
Available: Right Now
Listed: 01/05/2024
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...
$5,100
Available: Right Now
Listed: 29/04/2024
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...
$4,200
Available: Right Now
Listed: 29/04/2024
Chester, VT, 05143
Modern mountain retreat! This updated 3-bed, 2-bath home, close to premier ski resorts (Okemo 21 mins , Stratton 31 mins, Magic Mountain 17 mins and Bromley 28mins) offers contemporary design and cozy comfort. 38 mins away from the historic town of M...
$14,220
Available: Right Now
Listed: 30/04/2024
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...
$3,780
Available: Right Now
Listed: 26/04/2024
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...
$5,790
Available: Right Now
Listed: 27/04/2024
Chester, VT, 05143
⭐️ 2022 Rockingham Old House Award ⭐️Take it easy at this unique and tranquil getaway. The Cairn of Vermont is an 1840s stone house located in the sleepy remnants of Bartonsville Village, now part of Chester, VT. 20minutes to skiing and hiking, b...
$10,230
Available: Right Now
Listed: 30/04/2024
Chester, VT, 05143
Spacious, private and fully outfitted for a group getaway to Vermont, this 3-bedroom, 3-bath vacation rental is ready for 4 seasons of adventures! Set on 4 private acres with a wraparound deck for summertime relaxation, and a floor-to-ceiling stone f...