5/5 - Excellent
Verified traveler
Very friendly area and quaint!
Chester, VT
Travel Guide
Visit Chester
Where to stay in Chester
Chester Depot
4.5/5(15 area reviews)
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
$369 nightly
The price is $406 total per night from Nov 30 to Dec 1
$406 total
Nov 30 - Dec 1
Total with taxes and fees
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (548 reviews)
I’ve traveled a lot around the world and this hotel has to be in my top 3 ever. Especially beautiful in autumn
Reviewed on Nov 4, 2025
The Shire Woodstock
46 Pleasant St., Woodstock, VT
$167 nightly
The price is $184 total per night from Nov 17 to Nov 18
$184 total
Nov 17 - Nov 18
Total with taxes and fees
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (878 reviews)
Large, clean room with nice view. Unique.
Reviewed on Nov 9, 2025
Kimpton Taconic Hotel by IHG
3835 Main St., Manchester, VT
$194 nightly
The price is $213 total per night from Dec 1 to Dec 2
$213 total
Dec 1 - Dec 2
Total with taxes and fees
Stay at this 4-star golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property ...
9.2/10 Wonderful! (812 reviews)
No continental breakfast ,no microwave or in room coffeemaker. Only water or iced tea at check in , no coffee
Reviewed on Oct 25, 2025
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
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! (23 reviews)
Hidden gem!
This lovingly built off-grid glamping cabin is drenched with sun! It’s absolutely gorgeous! The kids enjoyed pumping their own water and sledding down the front hill. Paris is an excellent hostess- she answered all our questions very promptly & thoroughly. We cant wait to come back! Thank you!!!
Reviewed on Feb 24, 2025
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3387 East Mountain Road, Killington, VT
Stay at this 3-star ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage ...
9/10 Wonderful! (53 reviews)
Arrived after dark. Didn’t know where to park. Very secluded. Outside light would not stay lit. Upstairs needs attention.
Reviewed on Oct 27, 2025
Long Trail House at Stratton Mountain Resort
761 Stratton Access Rd, Stratton, VT
Stay at this 3-star ski aparthotel in Stratton. Enjoy free WiFi, free parking, and 10 restaurants. Popular attractions Stratton Mountain Resort and Villager ...
8.4/10 Very Good! (76 reviews)
Nice lodge. Room needs updating
Reviewed on Oct 19, 2025
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.
Popular places to visit
Bonnie's Bundles Dolls
Enjoy an outing to Bonnie's Bundles Dolls during your stay in Chester. Discover the area's mountain views, or seek out its ski slopes.
DaVallia Art & Accents
Enjoy an outing to DaVallia Art & Accents during your stay in Chester. You can seek out the ski slopes while in the area.
Reviews of Chester
4.2
Top Destination
4/5 - Good
Verified traveler
Quaint and beautiful town with good representation of Vermont.
4/5 - Good
Verified traveler
Cute, quiet little town.
5/5 - Excellent
BL
Chester is a cute little town. We went to ski at Okemo and this was the last place available, so we stumbled onto this property. Glad we did, going out to eat was much easier than in Ludlow and everyone we met couldn't be nicer.
4/5 - Good
Verified traveler
The Scottish Inn Pub was excellent!
3/5 - Okay
Verified traveler
Not much to it
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- Bonnie's Bundles Dolls
- DaVallia Art & Accents
- Stratton Mountain Resort
- Mount Snow
- Killington Resort
- Okemo Mountain Resort
- Bromley Mountain Ski Resort
- Magic Mountain Ski Resort
- Green Mountain National Forest
- Keene State College
- Mount Snow Golf Course
- Connecticut River
- Billings Farm and Museum
- Hildene
- Vermont Country Store
- Stratton Mountain Summit Gondola
- Equinox Preservation Trust
- Sunrise Village Triple Ski Lift
- Weston Playhouse
- Golf Club at Equinox
- American Express Ski Lift
- Manchester Designer Outlets
- The Stone Church
- Landmark College
- Connecticut Lakes Region
- Blow-Me-Down Bridge
- Historic Main Street
- Mt Ascutney State Park
- Bellows Falls Opera House
- Colonial Theatre
- Battenkill River
- Emerald Lake State Park
