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
$359 nightly
The price is $395 total per night from Nov 30 to Dec 1
$395 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! (544 reviews)
Great staff. Wonderful property, close to the village.
Reviewed on Oct 29, 2025
The Shire Woodstock
46 Pleasant St., Woodstock, VT
$153 nightly
The price is $168 total per night from Nov 2 to Nov 3
$168 total
Nov 2 - Nov 3
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! (867 reviews)
No balcony but nice river views. Parking just outside the door
Reviewed on Oct 29, 2025
Jackson Gore Village
111 Jackson Gore Road, Ludlow, VT
$205 nightly
The price is $226 total per night from Nov 2 to Nov 3
$226 total
Nov 2 - Nov 3
Total with taxes and fees
Stay at this 3-star spa hotel in Ludlow. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition ...
8.6/10 Excellent! (820 reviews)
The room overall was nice. There were lots of marks on the walls and baseboards. However everything was pretty clean and the fireplace was a nice touch. Unfortunately due to the time of the year we were on our own for food. I wish they told us this ahead of hour stay. Otherwise it was a nice.stay. ...
Reviewed on Oct 29, 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! (75 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
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.
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.
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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- DaVallia Art & Accents
- Bonnie's Bundles Dolls
- Killington Resort
- Okemo Mountain Resort
- Stratton Mountain Resort
- Mount Snow
- Green Mountain National Forest
- Bromley Mountain Ski Resort
- Magic Mountain Ski Resort
- Keene State College
- Golf Club at Equinox
- Vermont Country Store
- Connecticut River
- Equinox Preservation Trust
- Stratton Mountain Summit Gondola
- Billings Farm and Museum
- Hildene
- Mount Snow Golf Course
- Landmark College
- Manchester Designer Outlets
- Connecticut Lakes Region
- Mt Ascutney State Park
- American Express Ski Lift
- Historic Main Street
- Spofford Lake
- Blow-Me-Down Bridge
- Emerald Lake State Park
- Lake Rescue
- Colonial Theatre
- Sunrise Village Triple Ski Lift
- Molly Stark State Park
- Battenkill River