Chester Rentals
From $340 per night (USD)VRBO
King & Queen Suite in Historic Inn Circa 1780
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Enjoy a private room, bathroom, shower & Fireplace in the historic Chester Inn, circa 1780. This charming property is co ...
From $340 per night (USD)VRBO
From $230 per night (USD)VRBO
Cheerful residential home with lots of space
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Completely renovated spacious home, about 20 minutes from Okemo Mountain! 3 bedrooms, 2 1/2 bathrooms, pool table, air h ...
From $230 per night (USD)VRBO
From $349 per night (USD)VRBO
Log cabin near Okemo / Ludlow on 25 acres borders state forest w/trails nearby
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful hilltop cabin on 25 private acres bordering the William's River State Forest. Relax at this private retreat o ...
From $349 per night (USD)VRBO
From $288 per night (USD)Expedia
Circa 1868 Chester Home/Victorian Farmhouse-Less than 20 MIN TO OKEMO
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
OVERVIEW Our historic 1868 'Elm House' is located in the picturesque town of Chester, nestled in the heart of Chester De ...
From $288 per night (USD)Expedia
From $289 per night (USD)VRBO
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Sportsman themed, real log cabin that has comfortable wood stove & hearth, plus backup regular heat. Bathroom with show ...
From $289 per night (USD)VRBO
From $577 per night (USD)Expedia
UNIQUE/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy a historic stay in this former Chester Schoolhouse recently renovated into a massive yet cozy home. Located only 1 ...
From $577 per night (USD)Expedia
From $1129 per night (USD)VRBO
Work, Ski, Relax - Big Restored 1860s Farmhouse
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Come up solo or bring friends and family to our unique and lovingly renovated estate! Our charming 1860’s farmhouse slee ...
From $1129 per night (USD)VRBO
From $502 per night (USD)Expedia
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Gather with family and friends at our spacious home nestled in the Vermont woods. The Blue Moon Bungalow is your home a ...
From $502 per night (USD)Expedia
From $1007 per night (USD)VRBO
Cozy Vermont Cabin · Mountain Views · Near Okemo
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Nestled in the heart of the majestic Green Mountains, this charming 4-season retreat offers 12-acres of stunning views, ...
From $1007 per night (USD)VRBO
From $413 per night (USD)Expedia
Charming farmhouse, riverfront, views, woodstove, w/d, wifi, TV, kitchen, deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Country Riverside Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $413 per night (USD)Expedia
From $812 per night (USD)VRBO
Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 8
Lovingly updated antique 6 bedroom home in the historic Stone Village of Chester, VT. Sleeps 8+ comfortably making it t ...
From $812 per night (USD)VRBO
From $470 per night (USD)VRBO
Vacation Rental - Choose from 5 nearby mountains or relax in peace & comfort
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
This charming cabin offers 3 bedrooms, 2 full baths, a spacious living room area with wood burning stove, Finished basem ...
From $470 per night (USD)VRBO
From $155 per night (USD)VRBO
Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Adorable Cozy Cottage - sits on a mountainside with an OMG view- ideal for Cyclist, Skiers, Fall Leaf Peakers, Summer ge ...
From $155 per night (USD)VRBO
From $243 per night (USD)VRBO
Vermont Charm in the 1840 Gideon Lee House
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sunshine, flowers, Farmers' Markets, hikes and starry nights are here. Scents fill the air and the birds are calling. S ...
From $243 per night (USD)VRBO
From $442 per night (USD)VRBO
Spacious 5-bedroom chalet with AC and WiFi in charming Chester
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Discover this 5-bedroom gem in Chester. This charming chalet offers a serene and lovely retreat for guests. With a mix o ...
From $442 per night (USD)VRBO
From $360 per night (USD)Expedia
Historic Vermont farmhouse in 100+ acres, balcony, sunroom, office, window a/c
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Kingdom Valley Farmhouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $360 per night (USD)Expedia
From $133 per night (USD)VRBO
Quaint Queen room at the Chester Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a private room & bathroom with tub in the historic Chester Inn, circa 1780. This charming property is conveniently ...
From $133 per night (USD)VRBO
From $524 per night (USD)VRBO
Indoor Hot Tub Room/10 Miles to Okemo
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Great Central Vermont location! Private but easy to get too. Ten miles to Okemo/Jackson Gore. Skiing, golfing, hiking, s ...
From $524 per night (USD)VRBO
From $614 per night (USD)VRBO
Beautiful farmhouse in Historic village
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our beautiful and comfortable 1850s family farmhouse is modernly equipped and available for monthly stays through the se ...
From $614 per night (USD)VRBO
From $292 per night (USD)Expedia
Riverfront, family fun, amazing rec room, close to Magic & Okemo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Relax on the patio on the bank of the Williams River to watch the leaves turn, explore hiking trails, enjoy the outdoor ...
From $292 per night (USD)Expedia
From $352 per night (USD)VRBO
Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Ideal to host up to 6 guests, this home on 2 acres of land is a perfect retreat for anyone looking to be in the heart of ...
From $352 per night (USD)VRBO
From $399 per night (USD)Expedia
Chester Farmhouse Ski Retreat near Slopes
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our 4-bedroom Chester farmhouse—blending Vermont charm with mid-century style only 15 mins from Okemo, Magic ...
From $399 per night (USD)Expedia
From $651 per night (USD)VRBO
Maple Leaf Manor - 1864 Brick Federal Style Farmhouse with a modern touches.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Maple Leaf Manor provides its guests with a comfortable stay in a renovated 1864 Brick Federal Style Farmhouse on 8 acre ...
From $651 per night (USD)VRBO
From $125 per night (USD)Expedia
Hawks Mountain Farm, full apartment on a working farm.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Hello and welcome to Hawks Mountain Farm, a working farm with gardens, chickens, two yaks, four donkeys and an 1820 farm ...
From $125 per night (USD)Expedia
From $391 per night (USD)VRBO
Vermont Farmhouse Getaway Near the Slopes W/ Mtn Views, Free WiFi, Full Kitchen
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Vermont Mountain Farmhouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $391 per night (USD)VRBO
From $622 per night (USD)Expedia
Luxurious Mountain Cabin near Okemo with High-End Modern Amenities for up to 12
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Located in Ludlow, this professionally decorated home, with over 3000 Sq ft of living space, includes 4 bedrooms and 4 b ...
From $622 per night (USD)Expedia