Chester Rentals
- From $120 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 $120 per night (USD)VRBO
- From $119 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 $119 per night (USD)Expedia
- From $200 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 $200 per night (USD)VRBO
- From $318 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 $318 per night (USD)Expedia
- From $199 per night (USD)
VRBO
SPACIOUS VICTORIAN FARMHOUSE- 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 $199 per night (USD)VRBO
- From $127 per night (USD)
Expedia
1868 CARRIAGE HOUSE-QUAINT + COZY -PERFECT ESCAPE-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 $127 per night (USD)Expedia
- From $250 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 $250 per night (USD)VRBO
- From $276 per night (USD)
Expedia
Chester Home w\/ Views ~10 Mi to Okemo Mtn Resort!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Rest, relax, and enjoy the tranquil surroundings when you visit this vacation rental home in Chester, Vermont! The stunn ...
From $276 per night (USD)Expedia
- From $288 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 $288 per night (USD)VRBO
- From $474 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 $474 per night (USD)Expedia
- From $850 per night (USD)
VRBO
Work, Ski, Relax - Big Restored 1860s Farmhouse
- Bedrooms:
- 5
- 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 $850 per night (USD)VRBO
- From $200 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 $200 per night (USD)Expedia
- From $129 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 $129 per night (USD)VRBO
- From $361 per night (USD)
Expedia
Private Chester Home w\/ Deck, Mins to Skiing!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Spacious, private and fully outfitted for a group getaway to Vermont, this 3-bedroom, 3-bath vacation rental is ready fo ...
From $361 per night (USD)Expedia
- From $252 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 $252 per night (USD)VRBO
- From $641 per night (USD)
VRBO
Luxury stone farmhouse - lots of room! Perfect for families.
- 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 th ...
From $641 per night (USD)VRBO
- From $300 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 $300 per night (USD)VRBO
- From $125 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 $125 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Charming Vermont historic home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come to Vermont for springtime or beyond. Enjoy the emerging green of spring: daffodils, snowdrops, and crocuses are out ...
From $200 per night (USD)VRBO
- From $349 per night (USD)
VRBO
Amazing Vermont Farmhouse, ready for spring and summer bookings!!
- 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 $349 per night (USD)VRBO
- From $110 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 $110 per night (USD)VRBO
- From $273 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 $273 per night (USD)Expedia
- From $200 per night (USD)
VRBO
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 ...
From $200 per night (USD)VRBO
- From $270 per night (USD)
VRBO
Spring Skiing! Location! Minutes from Okemo!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover the perfect escape in the heart of a charming ski town. Our cozy and rustic home offers a peaceful retreat wher ...
From $270 per night (USD)VRBO
- From $450 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 $450 per night (USD)VRBO
- From $202 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 $202 per night (USD)Expedia
- From $255 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 $255 per night (USD)VRBO
- Click For Pricing
VRBO
Historic VT Grist Mill on the Williams River
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Located 12 miles from Okemo Mountain Ski Resort and Golf Club, this historic structure sits along the banks of the Willi ...
Click For PricingVRBO
- From $226 per night (USD)
VRBO
Stunning farmhouse in gorgeous historic village
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our beautiful and comfortable 1850s family farmhouse is modernly equipped and available for rent through the seasons. Sk ...
From $226 per night (USD)VRBO
- From $408 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 $408 per night (USD)Expedia
- From $480 per night (USD)
VRBO
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 $480 per night (USD)VRBO
- From $268 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 $268 per night (USD)Expedia
- From $350 per night (USD)
VRBO
12 Acre Getaway 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 $350 per night (USD)VRBO
- From $309 per night (USD)
Expedia
Large farmhouse w\/ Jacuzzi, Spring + Summer AVAIL
- 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 $309 per night (USD)Expedia
- From $234 per night (USD)
VRBO
Rustic, Cozy, and Entertaining home perfect for your next Vermont Adventure!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
-Listing The perfect home for your next Vermont getaway! Rustic, spacious, and peaceful home with plenty to do in the be ...
From $234 per night (USD)VRBO
- From $283 per night (USD)
Expedia
Modern Chalet with Serene Views - 15 Minutes to Okemo Mountain
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
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 ...
From $283 per night (USD)Expedia
- From $135 per night (USD)
VRBO
Contemporary Mountain Home near Okemo, Stratton, Magic Mountain and Bromley
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Modern mountain retreat! This updated 3-bed, 2-bath home, close to premier ski resorts (Okemo 21 mins , Stratton 31 mins ...
From $135 per night (USD)VRBO
- From $185 per night (USD)
Expedia
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 $185 per night (USD)Expedia
- From $209 per night (USD)
VRBO
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 $209 per night (USD)VRBO
- From $498 per night (USD)
VRBO
Maple Leaf Manor - 1864 Brick Federal Style Farmhouse with a modern touches.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Weekly and longer rentals for Summer. Maple Leaf Manor provides its guests with a comfortable stay in a renovated 1864 B ...
From $498 per night (USD)VRBO
- From $133 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 $133 per night (USD)VRBO
- From $164 per night (USD)
VRBO
Quaint rural farmhouse
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Indulge yourself in rural Vermont with this quaint 3 bedroom - 1 bedroom retreat! Located only 15 minutes from Okemo mou ...
From $164 per night (USD)VRBO
- From $188 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 $188 per night (USD)VRBO
- From $245 per night (USD)
Expedia
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 $245 per night (USD)Expedia
- From $146 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 $146 per night (USD)VRBO
- From $111 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 $111 per night (USD)Expedia
- From $228 per night (USD)
VRBO
Log Home Perfect for a Family Getaway - Five Miles from Okemo Mountain Resort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Sherman Log House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $228 per night (USD)VRBO
- Click For Pricing
Expedia
Beautiful home with pond views, tennis court, fireplace, hot tub, & washer\/dryer
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
East Hill Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For PricingExpedia
- From $234 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 $234 per night (USD)VRBO
- From $350 per night (USD)
VRBO
The Hideaway Chalet. 3bed + sleeping loft on 10 acres. Dog friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Situated on 10 acres, this cozy chalet has an open floor plan with a wall of windows to view Okemo Mt. Enjoy hot coffee ...
From $350 per night (USD)VRBO
- From $362 per night (USD)
VRBO
Luxurious Mountain Cabin near Okemo with High-End Modern Amenities for up to 12
- Bedrooms:
- 4
- 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 $362 per night (USD)VRBO
- From $546 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 $546 per night (USD)Expedia
- Click For Pricing
VRBO
Mountainside Retreat with Stunning Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience VT's Finest! This absolutely stunning home sits mountainside in Andover, Vermont. The view of the foliage is ...
Click For PricingVRBO
- Click For Pricing
VRBO
Retreat to this peaceful location and enjoy the private hot tub
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
This sprawling home welcomes you with open arms across its multiple levels, inviting you to savor the luxury of spacious ...
Click For PricingVRBO