Chester
Travel Guide
Visit Chester
Where to stay in Chester
Chester Depot
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 CA $176 per night from Apr 29 to Apr 30
CA $176
CA $192 total
Apr 29 - Apr 30
includes taxes & 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! (432 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
The price is CA $450 per night from May 10 to May 11
CA $450
CA $555 total
May 10 - May 11
includes taxes & 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! (572 reviews)
Wonderful historic property with warm and thoughtful staff. Even though some areas in the lobby were being refurbished, we still enjoyed the experience. Look forward to returning when the huge fireplace in the lobby is back up and operational.
Reviewed on Apr 10, 2026
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
The price is CA $189 per night from May 10 to May 11
CA $189
CA $216 total
May 10 - May 11
includes taxes & 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)
Super kind staff members. Our family arrived early, and they were able to find a room for us within an hour. Pool is clean as well!
Reviewed on Apr 15, 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! (59 reviews)
Great location and very nice place. Check in was smooth and communication was quick and efficient. Thank you.
Reviewed on Apr 20, 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! (237 reviews)
We had a wonderful stay! Thank you so much.
Reviewed on Apr 25, 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.
Things to do
Colonial Flintlock Musket Experience
CA $178
per adult
100% of travellers recommend
