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 7 to May 8
$141 total
May 7 - May 8
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! (433 reviews)
The staff were incredible and the property have the perfect vibes for a ski trip. The food was great and everything was very clean and comfy.
Reviewed on Apr 16, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$359 nightly
The price is $395 total per night from May 25 to May 26
$395 total
May 25 - May 26
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! (575 reviews)
Everything was excellent
Reviewed on May 5, 2026
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
$138 nightly
The price is $150 total per night from May 13 to May 14
$150 total
May 13 - May 14
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! (1,002 reviews)
Staff was amazing. I didnt catch her name, but she was wonderful
Reviewed on May 3, 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! (60 reviews)
It was great had no problems at all
Reviewed on May 2, 2026
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Mount Holly VT
Stay at this cabin in Mount Holly. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Okemo Mountain Resort and Lake Ninevah are located ...
9.8/10 Exceptional! (239 reviews)
This is our second year staying here. This place is very lovely. It’s quiet, secluded so it gives you the time alone that you need to just recoup and recover.
Reviewed on May 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.
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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- Enterprise Rental Cars in Chester Depot
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- DaVallia Art & Accents
- Bonnie's Bundles Dolls
- Stratton Mountain Resort
- Mount Snow
- Okemo Mountain Resort
- Killington Resort
- Green Mountain National Forest
- Bromley Mountain Ski Resort
- Magic Mountain Ski Resort
- Hildene
- Golf Club at Equinox
- Keene State College
- Billings Farm and Museum
- Equinox Preservation Trust
- Landmark College
- Weston Playhouse
- Spofford Lake
- The Stone Church
- Vermont Country Store
- Battenkill River
- Connecticut River
- Mount Snow Golf Course
- Manchester Designer Outlets
- Historic Main Street
- Marsh-Billings-Rockefeller National Historical Park
- Sunrise Village Triple Ski Lift
- Mt Ascutney State Park
- Emerald Lake State Park
- Woodstock Town Hall Theatre
