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, Bonnie's Bundles Dolls and DaVallia Art & Accents are top sights worth seeing.
Fullerton Inn
40 The Common Chester VT
$129 nightly
The price is $141 total per night from Mar 1 to Mar 2
$141 total
Mar 1 - Mar 2
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 ...
8.2/10 Very Good! (419 reviews)
Clean comfy room.
Reviewed on Feb 21, 2026
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
$144 nightly
The price is $157 total per night from Mar 3 to Mar 4
$157 total
Mar 3 - Mar 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! (989 reviews)
The staff was great, the room was large and comfortable. The bed linens, fluffy pillows and plush towels made the stay enjoyable. There were a couple things that could have made it better… the amenities included hot tub, and pool, but both were over run with kids. The hot tub small and completely ...
Reviewed on Feb 22, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$349 nightly
The price is $384 total per night from Mar 15 to Mar 16
$384 total
Mar 15 - Mar 16
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! (565 reviews)
Very clean, high end, friendly staff
Reviewed on Feb 20, 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.
Riverfront, family fun, amazing rec room, close to Magic & Okemo
Chester VT
Book a stay at this family-friendly vacation home in Chester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Bonnie's Bundles Dolls and ...
10/10 Exceptional! (14 reviews)
Clean, spacious, and well-equipped home that was a perfect fit for a ski weekend for our family of 6. The kids loved the turf play area and all the games!
Reviewed on Jan 24, 2026
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 ...
10/10 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 ...
8.6/10 Excellent! (83 reviews)
Great location - the room was very clean and spacious. You don't check in at the property but at another one nearby. Hot tub was nicely maintained
Reviewed on Jan 31, 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.
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
- Green Mountain National Forest
- Magic Mountain Ski Resort
- Golf Club at Equinox
- Connecticut River
- Keene State College
- Hildene
- Manchester Designer Outlets
- Mount Snow Golf Course
- Billings Farm and Museum
- Stratton Mountain Summit Gondola
- Landmark College
- American Express Ski Lift
- Sunrise Village Triple Ski Lift
- The Stone Church
- Colonial Theatre
- Vermont Country Store
- Lake Rescue
- Brattleboro Common
- Equinox Preservation Trust
- Stratton Mountain Golf Course
- Emerald Lake State Park
- Spofford Lake
