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
The price is SAR 484 per night from May 6 to May 7
SAR 484
SAR 527 total
includes taxes & fees
6 May - 7 May
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! (347 reviews)
"Excellent service to help resolve reservation mix up. Small but serviceable room. Very limited breakfast. On premises restaurant was excellent for dinner"
Reviewed on 22 March 2025
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is SAR 1,159 per night from May 26 to May 27
SAR 1,159
SAR 1,440 total
includes taxes & fees
26 May - 27 May
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! (515 reviews)
Beautiful Inn
"Gorgeous inn, staff was wonderful, beautiful lobby, library and other sitting rooms. Walking distance to shops and restaurants. Also a pet friendly inn."
Reviewed on 29 April 2025
The Equinox Golf Resort & Spa
3567 Main Street Route 7A, Manchester, VT
The price is SAR 407 per night from May 11 to May 12
SAR 407
SAR 648 total
includes taxes & fees
11 May - 12 May
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! (471 reviews)
"We a been coming to the Equinox multiple times a year for over 20 years but had not been here in over a year because the last time I was there it was not a pleasant experience. I am happy to say things are back to being very enjoyable again and we will be back soon!"
Reviewed on 25 April 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! (22 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 24 February 2025
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
Book a stay at this family-friendly vacation home in Winhall. Enjoy free WiFi, private hot tubs, and a garden. Popular attractions Stratton Mountain Resort and ...
9.6/10 Exceptional! (18 reviews)
Family visit
"This place was very enjoyable, it was just 3 of us so there was more than enough room. It is a very comfortable home and we enjoyed the easy trip into Manchester for some meals and a wonderful day of hiking some great nearby trails."
Reviewed on 16 April 2025
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Winhall
Stay at this cottage in Winhall. Enjoy free WiFi, a garden, and patios. Popular attractions Bromley Mountain Ski Resort and Bromley Alpine Slide are located ...
9.6/10 Exceptional! (189 reviews)
Amazing cabin
"Cabin was beautiful! Love the little stream outside. Very close to restaurants, shopping, and hiking trails."
Reviewed on 3 April 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
- DaVallia Art & Accents
- Bonnie's Bundles Dolls
- Stratton Mountain Resort
- Okemo Mountain Resort
- Mount Snow
- Killington Resort
- Keene State College
- Green Mountain National Forest
- Bromley Mountain Ski Resort
- Stratton Mountain Summit Gondola
- Magic Mountain Ski Resort
- Golf Club at Equinox
- Connecticut River
- Mount Ascutney
- Hildene
- Blow-Me-Down Bridge
- Vermont Country Store
- Equinox Preservation Trust
- Billings Farm and Museum
- Landmark College
- Vermont Summer Festival
- Mount Snow Golf Course
- Connecticut Lakes Region
- Manchester Designer Outlets
- Battenkill River
- Spofford Lake
- Saint-Gaudens National Historic Site
- Emerald Lake State Park
- Marsh-Billings-Rockefeller National Historical Park
- American Express Ski Lift
- The Stone Church
- Historic Main Street