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.
Fullerton Inn
40 The Common Chester VT
$129 nightly
The price is $141 total per night from Jan 13 to Jan 14
$141 total
Jan 13 - Jan 14
Total with taxes and fees
Stay at this inn in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8/10 Very Good! (405 reviews)
Nice staff
Reviewed on Jan 2, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$359 nightly
The price is $395 total per night from Jan 19 to Jan 20
$395 total
Jan 19 - Jan 20
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. ...
9.2/10 Wonderful! (558 reviews)
Luxurious and friendly resort! Loved it
Reviewed on Dec 18, 2025
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
$142 nightly
The price is $154 total per night from Feb 3 to Feb 4
$154 total
Feb 3 - Feb 4
Total with taxes and fees
Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (942 reviews)
Nice hotel! Very friendly staff and great value compared to other accommodations.
Reviewed on Jan 4, 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! (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
Long Trail House at Stratton Mountain Resort
761 Stratton Access Rd Stratton VT
Book a stay at this ski aparthotel in Stratton. Enjoy free WiFi, free parking, and 10 restaurants. Popular attractions Stratton Mountain Resort and Villager ...
8.4/10 Very Good! (78 reviews)
Nice lodge. Room needs updating
Reviewed on Oct 19, 2025
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 Pico Mountain at Killington ...
9/10 Wonderful! (57 reviews)
ample room, close to ski lifts, pretty view, great renovations, sauna was great, family had a wonderful time!
Reviewed on Dec 22, 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
- Okemo Mountain Resort
- Mount Snow
- Killington Resort
- Bromley Mountain Ski Resort
- Magic Mountain Ski Resort
- Green Mountain National Forest
- Keene State College
- Mount Snow Golf Course
- Stratton Mountain Summit Gondola
- Connecticut River
- Hildene
- Manchester Designer Outlets
- Sunrise Village Triple Ski Lift
- Golf Club at Equinox
- Vermont Country Store
- Billings Farm and Museum
- American Express Ski Lift
- Weston Playhouse
- Historic Main Street
- Spofford Lake
- Viking Nordic Center
- The Stone Church
- Landmark College
- Blow-Me-Down Bridge
- Connecticut Lakes Region
- Bear Mountain Quad Ski Lift
- Equinox Preservation Trust
- Colonial Theatre
