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.
The Shire Woodstock
46 Pleasant St., Woodstock, VT
$155 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 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! (839 reviews)
"We arrived later in the evening so we did not actually interact with staff in person, however, the communication with staff through text worked great. We stayed in the River House and the room was very nice, clean and comfortable. We enjoyed the adirondack chairs outside of our room overlooking the ..."
Reviewed on Oct 4, 2025
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
$449 nightly
The price is $494 total per night from Nov 2 to Nov 3
$494 total
Nov 2 - Nov 3
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! (534 reviews)
"Clean room. Staff very polite and helpful"
Reviewed on Sep 24, 2025
The Equinox Golf Resort & Spa
3567 Main Street Route 7A, Manchester, VT
$172 nightly
The price is $189 total per night from Nov 2 to Nov 3
$189 total
Nov 2 - Nov 3
Total with taxes and fees
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our ...
7.2/10 Good! (543 reviews)
"It’s a lovely 200 year old hotel that’s been updated nicely. It’s got 3 restaurants and a wonderful coffee bar in the lobby. The staff is very helpful and courteous."
Reviewed on Oct 3, 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! (49 reviews)
"Great value, comfortable space, responsive host!"
Reviewed on Aug 13, 2025
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
Townshend, VT
Stay at this lodge in Townshend. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Townshend State Park and Moore Free Library are located ...
10/10 Exceptional! (1 review)
"Had a great time . Excellent communication Very clean .Would definitely stay there again."
Reviewed on Oct 5, 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
