Chester Rentals
From $151 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 $151 per night (USD)VRBO
From $160 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 $160 per night (USD)Expedia
From $297 per night (USD)VRBO
1794 Pioneer House - Renovated, No Cleaning Fee
- Bedrooms:
- 2
- 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 $297 per night (USD)VRBO
From $387 per night (USD)Expedia
Log Home Perfect for a Family Getaway - Five Miles from Okemo Mountain Resort
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Sherman Log House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $387 per night (USD)Expedia
From $255 per night (USD)VRBO
Cheerful residential home with lots of space
- Bedrooms:
- 3
- 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 $255 per night (USD)VRBO
From $377 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 $377 per night (USD)Expedia
From $266 per night (USD)VRBO
Charming Historic Home in Vermont
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunshine, flowers, Farmers' Markets, hikes and starry nights are here. Scents fill the air and the birds are calling. S ...
From $266 per night (USD)VRBO
From $309 per night (USD)Expedia
Circa 1868 Chester Home-Less than 20 MIN TO OKEMO
- Bedrooms:
- 3
- 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 $309 per night (USD)Expedia
From $616 per night (USD)VRBO
Luxurious Mountain Cabin near Okemo with High-End Modern Amenities for up to 12
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Located in Ludlow, this professionally decorated home, with over 3000 Sq ft of living space, includes 4 bedrooms and 4 b ...
From $616 per night (USD)VRBO
From $213 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 $213 per night (USD)Expedia
From $260 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 $260 per night (USD)VRBO
From $128 per night (USD)Expedia
Hawks Mountain Farm, full apartment on a working farm.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Hello and welcome to Hawks Mountain Farm, a working farm with gardens, chickens, two yaks, four donkeys and an 1820 farm ...
From $128 per night (USD)Expedia
From $567 per night (USD)VRBO
Chester Home w\/ Views ~ 10 Mi to Okemo Mtn Resort!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
Rest, relax, and enjoy the tranquil surroundings when you visit this vacation rental home in Chester, Vermont! The stunn ...
From $567 per night (USD)VRBO
From $595 per night (USD)Expedia
The Full Vermont Experience, minutes from Okemo: Transcend to the VT Life
- Bedrooms:
- 3
- 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 $595 per night (USD)Expedia
From $532 per night (USD)VRBO
Ski Okemo, Killington, Magic & Bromley
- Bedrooms:
- 2
- 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 $532 per night (USD)VRBO
From $525 per night (USD)VRBO
Amazing Custom Home on 40+ Acres
- Bedrooms:
- 6
- Bathrooms:
- 6
- 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 $525 per night (USD)VRBO
From $431 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 $431 per night (USD)VRBO
From $818 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 $818 per night (USD)VRBO
From $323 per night (USD)VRBO
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 10
Welcome to 'Smokeshire Hilltop Farmhouse!' This lovely 5-bedroom, 2-bathroom vacation rental sits on a plateau above the ...
From $323 per night (USD)VRBO
From $524 per night (USD)VRBO
Indoor Hot Tub Room\/10 Miles to Okemo
- Bedrooms:
- 5
- 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 $709 per night (USD)VRBO
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 $709 per night (USD)VRBO
From $1019 per night (USD)Expedia
Work, Ski, Relax - Big Restored 1860s Farmhouse
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 12
Come up solo or bring friends and family to our unique and lovingly renovated estate! Our charming 1860’s farmhouse slee ...
From $1019 per night (USD)Expedia
From $151 per night (USD)VRBO
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 $151 per night (USD)VRBO
From $178 per night (USD)Expedia
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 $178 per night (USD)Expedia
From $465 per night (USD)VRBO
Private Chester Home w\/ Deck, Mins to Skiing!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Spacious, private and fully outfitted for a group getaway to Vermont, this 3-bedroom, 3-bath vacation rental is ready fo ...
From $465 per night (USD)VRBO
From $140 per night (USD)VRBO
Vermont Hillside Cottage w\/Great View - Pet Friendly
- 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 $140 per night (USD)VRBO
From $400 per night (USD)VRBO
Stunning farmhouse-Historic village-Mins to Skiing
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Our beautiful and comfortable 1850s family farmhouse is modernly equipped and available for rent through the seasons. Sk ...
From $400 per night (USD)VRBO
From $595 per night (USD)Expedia
15 Minutes to ski Okemo - Mountain views from this magical log home on 6 acres
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This incredible log home is the perfect spot for a weekend getaway or an extended stay in Vermont. Nestled on 6 acres of ...
From $595 per night (USD)Expedia
From $156 per night (USD)VRBO
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
- Bedrooms:
- 1
- 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)VRBO
From $557 per night (USD)Expedia
Farmhouse w\/ mountain views close to skiing. Includes outdoor sauna EV CHRGR
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Experience 180 degrees mountain views at this quaint farmhouse. World Class Skiing at Okemo Mountain is just 23 mins, B ...
From $557 per night (USD)Expedia
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Spacious retreat with private hot tub, game room, deck, fireplace, & W\/D
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 13
Okemo Valley Chalet Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
Click For PricingVRBO
From $452 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 $452 per night (USD)VRBO
From $288 per night (USD)VRBO
Tranquility awaits for your stay at our cherished log home on 6 secluded acres.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our cozy log home nestled on 6 acres of picturesque Vermont countryside. If you're seeking a peaceful and rej ...
From $288 per night (USD)VRBO
From $359 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 $359 per night (USD)Expedia
From $286 per night (USD)VRBO
Zen of the Woods Tiny Cabin in Okemo Valley
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Zen of the Woods! A cozy, thoughtfully designed tiny cabin retreat minutes from Okemo. Set amongst hundreds o ...
From $286 per night (USD)VRBO
From $446 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 $446 per night (USD)Expedia
From $468 per night (USD)VRBO
Gorgeous views near Stratton & Okemo
- 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 $468 per night (USD)VRBO
From $481 per night (USD)Expedia
Rustic 150-year-old farmhouse, Jacuzzi included\n\n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Farmhouse of VT. Step back in time in this 1869 farmhouse, showcasing both antique rustic furnishings, co ...
From $481 per night (USD)Expedia
From $376 per night (USD)VRBO
Charming Chester Farmhouse – peaceful and close to everything!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this charming farmhouse on a peaceful residential street close to the heart of Chester. This home has comfor ...
From $376 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 $847 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 $847 per night (USD)VRBO
From $556 per night (USD)Expedia
Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to the Riverbend, a designer Southern Vermont farmhouse <10 minutes from Magic Mountain! This newly renovated hi ...
From $556 per night (USD)Expedia
From $173 per night (USD)VRBO
Cozy Farmhouse in Chester
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
This is our very cozy 1850 home in the Stone Village of Chester. The house has many of the original features and charm i ...
From $173 per night (USD)VRBO
From $1086 per night (USD)Expedia
WhiSki Cabin - 12 Acres With a Mountain View!
- 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 $1086 per night (USD)Expedia
From $289 per night (USD)VRBO
This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Sage House at Camp Greenwood: a brand new micro tiny house village central to the best attractions in Souther ...
From $289 per night (USD)VRBO
From $386 per night (USD)Expedia
This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Thistle House at Camp Greenwood: a brand new micro tiny house village central to the best attractions in Sout ...
From $386 per night (USD)Expedia
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Majestic mountain escape, 4BR, stunning views, hot tub, fireplace, BBQ, w&d
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Mont House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
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From $492 per night (USD)VRBO
Spacious 5-bedroom Stone House in Historic Chester 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 $225 per night (USD)VRBO
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Pet Friendly (w/ Fee) | Close to Hiking & Skiing | On-Site Goats | Foliage Views From crisp autumn mornings to snowy wi ...
From $225 per night (USD)VRBO
From $479 per night (USD)Expedia
Charming farmhouse, riverfront, views, woodstove, w\/d, wifi, TV, kitchen, deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Country Riverside Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $479 per night (USD)Expedia
From $601 per night (USD)VRBO
Spacious dog-friendly house w\/ woodstove, fenced-in yard, BBQ, wifi, w\/d, TV
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Town & Mountain Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $601 per night (USD)VRBO
From $198 per night (USD)Expedia
3-bedrooms and bath in welcoming Chester with WiFi, AC.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Unwind in Chester at this lovely apartment. With 3 nice bedrooms, WiFi, AC, and heating, guests will feel right at home. ...
From $198 per night (USD)Expedia
From $375 per night (USD)VRBO
Cozy farmhouse w\/ TV, wifi, w\/d, dvd player, kitchen, board games
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
House At Dream Barn Hollow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $375 per night (USD)VRBO
From $334 per night (USD)Expedia
Spacious 5-bedroom chalet with AC and WiFi in charming Chester
- Bedrooms:
- 3
- 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 $334 per night (USD)Expedia
From $384 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 $384 per night (USD)VRBO