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 May 28 to May 29
$141 total
May 28 - May 29
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! (435 reviews)
"Very nice older Inn with on-site tavern in a classic Vermont town. Quite and comfortable stay."
Reviewed on May 22, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$449 nightly
The price is $494 total per night from May 31 to Jun 1
$494 total
May 31 - Jun 1
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. ...
9.4/10 Exceptional! (580 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."
Reviewed on May 22, 2026
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
$144 nightly
The price is $156 total per night from Jun 4 to Jun 5
$156 total
Jun 4 - Jun 5
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! (1,000 reviews)
"Hotel is not near any resturants and it had no on-premisis restaurant for breakfast."
Reviewed on May 17, 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! (24 reviews)
"I had a great stay! Everything was as shown and described in the listing. My only advice is-if you are staying there during mud season make sure you have a AWD/4WD vehicle-the road to the property can get pretty bad."
Reviewed on Mar 11, 2026
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 Skyeship Express Gondola Stage ...
9/10 Wonderful! (62 reviews)
"Very quiet location secluded and peaceful. Location is not identified, no road sign or driveway entrance address. I booked within 3 days of check-in, instructions did not get emailed until after check in time, host did answer phone when called but email was received 30 minutes later. It's a unique ..."
Reviewed on May 10, 2026
Mountainside 5-BR Ski-In/Out Okemo Villa
Ludlow VT
Stay at this vacation home in Ludlow. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Okemo Mountain Resort and Quantum Ski Lift ...
9.8/10 Exceptional! (6 reviews)
Fantastic Ski in Ski out location
"Amazing house"
Reviewed on Feb 24, 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.
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- DaVallia Art & Accents
- Bonnie's Bundles Dolls
- Stratton Mountain Resort
- Okemo Mountain Resort
- Killington Resort
- Mount Snow
- Green Mountain National Forest
- Bromley Mountain Ski Resort
- Billings Farm and Museum
- Magic Mountain Ski Resort
- Landmark College
- Battenkill River
- Hildene
- Keene State College
- Golf Club at Equinox
- Equinox Preservation Trust
- Manchester Designer Outlets
- Vermont Country Store
- Spofford Lake
- Emerald Lake State Park
- The Stone Church
- Calvin Coolidge Historic Site
- Mount Snow Golf Course
- Stratton Mountain Summit Gondola
- Jamaica State Park
- Mt Ascutney State Park
- Brattleboro Common
- Connecticut River
- Sunrise Village Triple Ski Lift
- Woodstock Town Hall Theatre