Skip to Main Content.
Download the app button
Download the app button with download icon
Get the app
Canada
Trip Boards
List your property
Help
My trips
Sign in
It's easy to contact hosts and keep track of all your messages when you have a Vrbo account
Traveller login
Sign in as an owner
Create a free account
Feedback
Going to
Going to
Dates
Dates
Travellers
Adults
Adults
Decrease the number of adults
Increase the number of adults
Children
Ages 0 to 17
Decrease the number of children
Increase the number of children
I am travelling with pets
If checked, only properties that allow pets will be shown
Done
Search
Filters
Popular
Price
Rooms & spaces
Sort by recommended
300+ properties
How our sort order works
Opens in a new window
Search results showing properties in Chester, Vermont, United States of America
Google map showing 500 properties
Photo gallery for Zen of the Woods Tiny Cabin in Okemo Valley
Zen of the Woods Tiny Cabin
Show previous image for Zen of the Woods Tiny Cabin in Okemo Valley
Show next image for Zen of the Woods Tiny Cabin in Okemo Valley
Premier Host
Cabin · 4.9 mi (7.9 km) to Chester center
Zen of the Woods Tiny Cabin in Okemo Valley
Sleeps 4 · 1 bedroom · 1 bathroom
10
10 out of 10
Exceptional
exceptional
6 reviews
(6 reviews)
Unavailable
More information about Zen of the Woods Tiny Cabin in Okemo Valley, opens in a new tab
Photo gallery for Vermont Hillside Cottage w/Great View - Pet Friendly
It doesn't get more Vermont than this
Show previous image for Vermont Hillside Cottage w/Great View - Pet Friendly
Show next image for Vermont Hillside Cottage w/Great View - Pet Friendly
House · 4.4 mi (7.1 km) to Chester center
Vermont Hillside Cottage w/Great View - Pet Friendly
Sleeps 4 · 2 bedrooms · 1 bathroom
10
10 out of 10
Exceptional
exceptional
177 reviews
(177 reviews)
Unavailable
More information about Vermont Hillside Cottage w/Great View - Pet Friendly, opens in a new tab
Photo gallery for Whimsical Room & Private Bathroom in Historic Inn
Room
Show previous image for Whimsical Room & Private Bathroom in Historic Inn
Show next image for Whimsical Room & Private Bathroom in Historic Inn
House · Within Chester Depot
Whimsical Room & Private Bathroom in Historic Inn
Sleeps 3 · 1 bedroom · 1 bathroom
10
10 out of 10
Exceptional
exceptional
3 reviews
(3 reviews)
Unavailable
More information about Whimsical Room & Private Bathroom in Historic Inn, opens in a new tab
House · 4.2 mi (6.8 km) to Chester center
Cheerful residential home with lots of space
Sleeps 8 · 3 bedrooms · 2+ bathrooms
10
10 out of 10
Exceptional
exceptional
17 reviews
(17 reviews)
Unavailable
More information about Cheerful residential home with lots of space, opens in a new tab
Bed & breakfast · Within Chester Depot
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Sleeps 3 · 1 bedroom · 1 bathroom
Unavailable
More information about Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! , opens in a new tab
House · Within Chester Depot
Charming Vermont historic home
Sleeps 6 · 2 bedrooms · 1+ bathroom
10
10 out of 10
Exceptional
exceptional
14 reviews
(14 reviews)
Unavailable
More information about Charming Vermont historic home, opens in a new tab
Bed & breakfast · Within Chester Depot
Room in Historic Inn! 20 Minutes to Okemo!
Sleeps 3 · 1 bedroom · 1 bathroom
9.0
9.0 out of 10
Wonderful
wonderful
10 reviews
(10 reviews)
Unavailable
More information about Room in Historic Inn! 20 Minutes to Okemo!, opens in a new tab
Countryside · 4.3 mi (7 km) to Chester center
Quaint rural farmhouse
Sleeps 6 · 3 bedrooms · 2 bathrooms
Unavailable
More information about Quaint rural farmhouse, opens in a new tab
House · 4.3 mi (6.9 km) to Chester center
Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!
Sleeps 9 · 4 bedrooms · 3 bathrooms
10
10 out of 10
Exceptional
exceptional
33 reviews
(33 reviews)
Unavailable
More information about Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!, opens in a new tab
Cabin · 3.1 mi (5 km) to Chester center
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
Sleeps 5 · 1 bedroom · 1 bathroom
9.8
9.8 out of 10
Exceptional
exceptional
70 reviews
(70 reviews)
Unavailable
More information about Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!, opens in a new tab
Guesthouse · Within Chester Depot
1868 CARRIAGE HOUSE-QUAINT + COZY -PERFECT ESCAPE-20 MIN TO OKEMO!
Sleeps 6 · 3 bedrooms · 1 bathroom
9.6
9.6 out of 10
Exceptional
exceptional
33 reviews
(33 reviews)
Unavailable
More information about 1868 CARRIAGE HOUSE-QUAINT + COZY -PERFECT ESCAPE-20 MIN TO OKEMO!, opens in a new tab
Apartment · 1 mi (1.5 km) to Chester center
This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT.
Sleeps 2 · 1 bedroom · 1 bathroom
10
10 out of 10
Exceptional
exceptional
2 reviews
(2 reviews)
Unavailable
More information about This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT., opens in a new tab
House · Within Chester Depot
Charming Chester Farmhouse – peaceful and close to everything!
Sleeps 8 · 4 bedrooms · 1+ bathroom
9.6
9.6 out of 10
Exceptional
exceptional
5 reviews
(5 reviews)
Unavailable
More information about Charming Chester Farmhouse – peaceful and close to everything!, opens in a new tab
House · 4.2 mi (6.7 km) to Chester center
Contemporary Mountain Home near Okemo, Stratton, Magic Mountain and Bromley
Sleeps 8 · 3 bedrooms · 2 bathrooms
10
10 out of 10
Exceptional
exceptional
2 reviews
(2 reviews)
Unavailable
More information about Contemporary Mountain Home near Okemo, Stratton, Magic Mountain and Bromley, opens in a new tab
Cabin · 5.6 mi (9.1 km) to Chester center
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Sleeps 4 · 2 bedrooms · 0+ bathrooms
9.8
9.8 out of 10
Exceptional
exceptional
18 reviews
(18 reviews)
Unavailable
More information about Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area, opens in a new tab
House · 5.6 mi (9.1 km) to Chester center
Indoor Hot Tub Room/10 Miles to Okemo
Sleeps 8 · 5 bedrooms · 4+ bathrooms
Unavailable
More information about Indoor Hot Tub Room/10 Miles to Okemo, opens in a new tab
House · Within Chester Depot
SPACIOUS VICTORIAN FARMHOUSE- 20 MIN TO OKEMO
Sleeps 8 · 4 bedrooms · 2+ bathrooms
9.8
9.8 out of 10
Exceptional
exceptional
30 reviews
(30 reviews)
Unavailable
More information about SPACIOUS VICTORIAN FARMHOUSE- 20 MIN TO OKEMO, opens in a new tab
Bed & breakfast · Within Chester Depot
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Sleeps 3 · 1 bedroom · 1 bathroom
8.0
8.0 out of 10
Very good
very good
5 reviews
(5 reviews)
Unavailable
More information about Honeymoon Suite with Jacuzzi Tub in Historic Inn, opens in a new tab
Tell us how we can improve our site
Share feedback
