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! (598 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! (860 reviews)
"Excellent amenities and perfect if you're traveling with a dog to VT. Rooms are very nice albeit a bit small and very low water pressure in the shower."
Reviewed on Aug 3, 2026
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
485 Hotel Road Brownsville VT
$154 nightly
The price is $168 total per night from Aug 17 to Aug 18
$168 total
Aug 17 - Aug 18
Total with taxes and fees
Stay at this resort in Brownsville. Enjoy a business center, a fireplace in the lobby, and laundry facilities. Our guests praise the helpful staff in our reviews. ...
9/10 Wonderful! (863 reviews)
"Perfect"
Reviewed on Aug 7, 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.
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! (48 reviews)
"The best place in Vermont! Fantastic amenities, and close to some wonderful little towns. The property is absolutely gorgeous and the host was incredible! This was our second time returning to the cabin and it will not be our last!!!"
Reviewed on Aug 9, 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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- Mt Ascutney State Park
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- Molly Stark State Park