Chester, VT
Travel Guide


Visit Chester
Where to stay in Chester
Find the best Chester areas and neighborhoods for the activities you enjoy most. Learn more about Chester
Learn more about Chester

Chester Depot
If you're spending some time in Chester Depot, DaVallia Art & Accents and Bonnie's Bundles Dolls are top sights worth seeing.

Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$449 nightly
The price is $494 total per night from Sep 7 to Sep 8
$494 total
Sep 7 - Sep 8
Total with taxes and fees
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (599 reviews)
"Amazing! Will visit again."
Reviewed on Aug 7, 2026

Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
$257 nightly
The price is $283 total per night from Sep 9 to Sep 10
$283 total
Sep 9 - Sep 10
Total with taxes and fees
Book a stay at this golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (862 reviews)
"A few unexpected extra charges for property fees"
Reviewed on Aug 17, 2026

On The River Inn
1653 West Woodstock Road Woodstock VT
$249 nightly
The price is $274 total per night from Sep 8 to Sep 9
$274 total
Sep 8 - Sep 9
Total with taxes and fees
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Chester VT
Stay at this cabin in Chester. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial ...
9.8/10 Exceptional! (25 reviews)
"This is an adorable and cozy cabin surrounded by nature - from which you can hear a soothing stream from your window. If you are looking for a place to restore in nature and unplug "glamping-style" - yet close to shops/coffee/outings, etc., - this little blue cabin is the perfect spot. I liked that ..."
Reviewed on Jul 6, 2026

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3387 East Mountain Road Killington VT
Book a stay at this ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage ...
9.2/10 Wonderful! (67 reviews)
"Nice area, clean and kitchen was well equipped. We used the air fryer for dinner one night."
Reviewed on Aug 15, 2026

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish VT
Stay at this cabin in Cavendish. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Phineas Gage Memorial and Mount Ascutney are located ...
10/10 Exceptional! (53 reviews)
"The cabins are a great getaway, stocked with everything you need for a comfortable stay in the woods. They have nice kitchens and comfortable beds, heat and AC, outdoor grills and firepits. The hot tub is a great way to relax after a day of hiking or skiing."
Reviewed on Aug 24, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Chester attractions
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- Visit Springfield
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- Visit Jamaica
- Vermont Country Store
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- Killington Resort
- Visit Reading
- Visit Southern Vermont
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- Bonnie's Bundles Dolls
- Visit Weathersfield
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- Visit Peru
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- Chester Vacations
- Visit Saxtons River
- Vermont Museum of Mining and Minerals
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- Bonnie's Bundles Dolls
- DaVallia Art & Accents
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- Mount Snow
- Killington Resort
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- Green Mountain National Forest
- Bromley Mountain Ski Resort
- Magic Mountain Ski Resort
- Connecticut River
- Keene State College
- Vermont Marketplace
- Stratton Mountain Summit Gondola
- Vermont Country Store
- Landmark College
- The Stone Church
- Hildene
- Billings Farm and Museum
- Historic Main Street
- Emerald Lake State Park
- Golf Club at Equinox
- Sunrise Village Triple Ski Lift
- Spofford Lake
- Manchester Designer Outlets
- Molly Stark State Park
- Cornish-Windsor Covered Bridge
- Lake Rescue
- Mt Ascutney State Park
- Battenkill River
- Mount Snow Golf Course



