Chester Rentals
From $167 per night (USD)VRBO
Room in Historic Inn! 20 Minutes to Okemo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy a private room, bathroom & shower in the historic Chester Inn, circa 1780. This charming property is conveniently ...
From $167 per night (USD)VRBO
From $340 per night (USD)Expedia
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)Expedia
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)Expedia
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)Expedia
From $288 per night (USD)VRBO
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)VRBO
From $209 per night (USD)Expedia
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and taverns, antique shops, ...
From $209 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 $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 $321 per night (USD)VRBO
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to 'Smokeshire Hilltop Farmhouse!' This lovely 5-bedroom, 2-bathroom vacation rental sits on a plateau above the ...
From $321 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 $155 per night (USD)Expedia
Whimsical Room & Private Bathroom in Historic Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy a private room & bathroom with tub in the historic Chester Inn, circa 1780. This charming property is conveniently ...
From $155 per night (USD)Expedia
From $269 per night (USD)VRBO
Honeymoon Suite with Jacuzzi Tub in Historic Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy a private room, bathroom & shower in the historic Chester Inn, circa 1780. This charming property is conveniently ...
From $269 per night (USD)VRBO
From $1007 per night (USD)Expedia
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)Expedia
From $413 per night (USD)VRBO
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)VRBO
From $492 per night (USD)VRBO
Spacious 5-bedroom Historic Stone House near Okemo
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
This home is located in the heart of the Stone Village in Chester and was built in 1844 by the Clark brothers. This is o ...
From $492 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 $643 per night (USD)VRBO
Amazing Vermont Farmhouse, perfect for summer and fall foliage getaways!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Looking for the perfect Vermont escape? Mountain views, cool breezes, fall leaves and newly fallen snow...all of this an ...
From $643 per night (USD)VRBO
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 $510 per night (USD)VRBO
Amazing Custom Home on 40+ Acres
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Beautiful views and lots of privacy but still only 2 miles from town. 5 bedrooms and 6 bathrooms with exercise room, gam ...
From $510 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 $294 per night (USD)VRBO
FOUR SEASON HOME NEAR OKEMO
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy our newly renovated 3 BR home in the idyllic town of Chester. A great getaway for any of the Four Seasons. 15 minu ...
From $294 per night (USD)VRBO
From $268 per night (USD)Expedia
Thistle House at Camp Greenwood Vermont with Sauna
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Welcome to Thistle House, a custom-built cedar tiny home surrounded by seven acres of natural landscape in beau ...
From $268 per night (USD)Expedia
From $255 per night (USD)VRBO
Sage House at Camp Greenwood Vermont with Sauna
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Welcome to Sage House, a custom-built cedar tiny home surrounded by seven acres of natural landscape in beautif ...
From $255 per night (USD)VRBO
From $226 per night (USD)VRBO
Hike, Ski & Unwind: Cabin w/ Deck in Chester!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Scenic Views | Year-Round Activities | Near Outdoor Recreation Step into the rustic charm of Chester at this 3-bedroom, ...
From $226 per night (USD)VRBO
From $351 per night (USD)VRBO
Spacious 5-bedroom cabin in charming Chester
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Relax with the whole family at this perfect all season VT retreat. Nestled into a hill, surrounded by scenic views. Cent ...
From $351 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 $156 per night (USD)Expedia
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
- Bedrooms:
- 0
- Bathrooms:
- 2
- Sleeps:
- 4
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 ...
From $156 per night (USD)Expedia
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 $347 per night (USD)VRBO
Bright and spacious 3 Bed/3 Bath in Chester, VT
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This bright and spacious 3 bed/3 bath home is within walking distance of shops, restaurants, a local pub, and small groc ...
From $347 per night (USD)VRBO
From $189 per night (USD)VRBO
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Pet Friendly w/ Fee (Max 1) | Close to Hiking & Skiing | On-Site Goats | Foliage Views From crisp autumn mornings to sn ...
From $189 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)VRBO
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)VRBO
From $352 per night (USD)Expedia
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)Expedia
From $520 per night (USD)VRBO
Renovated ski house near Okemo and Stratton
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
You will enjoy Vermont at this beautifully renovated house set on 12 acres in the quaint town of Chester. You can relax ...
From $520 per night (USD)VRBO
From $449 per night (USD)Expedia
Historic 150-year-old farmhouse, Jacuzzi included
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Farmhouse of VT - your perfect Vermont recharge spot. Step back in time in this large 1869 farmhouse, wh ...
From $449 per night (USD)Expedia
From $399 per night (USD)VRBO
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)VRBO
From $161 per night (USD)Expedia
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy a private room, bathroom & shower in the historic Chester Inn, circa 1780. This charming property is conveniently ...
From $161 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 $562 per night (USD)Expedia
The Full Vermont Experience, minutes from Okemo: Transcend to the VT Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Ski Okemo? Check Sledding in the back yard? Check Ice Skating on your own pond? Check Snowshoeing in your own trails? Ch ...
From $562 per night (USD)Expedia
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 $484 per night (USD)Expedia
Log Home Perfect for a Family Getaway - Five Miles from Okemo Mountain Resort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Sherman Log House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $484 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 $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 $622 per night (USD)VRBO
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)VRBO
From $271 per night (USD)VRBO
1794 Pioneer House - Renovated, No Cleaning Fee
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Pioneer House is a unique survivor from Vermont’s earliest days. 100% solar powered (panels located on owner’s nearb ...
From $271 per night (USD)VRBO
From $445 per night (USD)VRBO
Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to the Riverbend, a designer Southern Vermont farmhouse <10 minutes from Magic Mountain! This newly renovated hi ...
From $445 per night (USD)VRBO