Chester, VT
Travel Guide
Visit Chester
Where to stay in Chester
Find the best Chester areas and neighborhoods for the activities you enjoy most. Learn more about Chester
Learn more about 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.
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
The price is NT$13,036 per night from Sep 7 to Sep 8
NT$13,036
NT$15,742 total
Sep 7 - Sep 8
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! (599 reviews)
"Amazing! Will visit again."
Reviewed on 2026/8/7
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
The price is NT$6,982 per night from Sep 9 to Sep 10
NT$6,982
NT$9,012 total
Sep 9 - Sep 10
includes taxes & fees
Book a stay at this golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (862 reviews)
"A few unexpected extra charges for property fees"
Reviewed on 2026/8/17
On The River Inn
1653 West Woodstock Road Woodstock VT
The price is NT$7,304 per night from Sep 10 to Sep 11
NT$7,304
NT$8,735 total
Sep 10 - Sep 11
includes taxes & fees
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
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.
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 ...
9.2/10 Wonderful! (67 reviews)
"Nice area, clean and kitchen was well equipped. We used the air fryer for dinner one night."
Reviewed on 2026/8/15
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 2026/1/31
Okemo Mountain Lodging by Vail Resorts
77 Okemo Ridge Rd Ludlow VT
Stay at this vacation home in Ludlow. Enjoy free parking, laundry facilities, and cable TV channels. Popular attractions Okemo Mountain Resort and Skywalker ...
7.8/10 Good! (28 reviews)
"Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband ..."
Reviewed on 2025/6/26
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.
Stay near popular Chester attractions
Explore a world of travel with Expedia
- B&B in Landgrove
- Pet-Friendly Hotels in Grafton
- Family Hotels in Londonderry
- Hotels near Green Mountain Sugar House
- Hotels near Bonnie's Bundles Dolls
- Hotel Wedding Venues Hotels in Proctorsville
- Pet-Friendly Hotels in Ludlow
- Hotel Wedding Venues Hotels in Chester
- Hotels with Bars in Ludlow
- B&B in Weston
- Hotel with a Concierge Hotels in Bellows Falls
- 5 Star Hotels in Springfield
- Hotels near Plummer's Sugar House
- Romantic Hotels in Chester
- Intrawest Corporation Hotels in Rockingham
- Hotels near Mt Ascutney State Park
- Hotels near Jamaica State Park
- Pet-Friendly Hotels in Chester
- Luxury Hotels in Bromley Mountain
- Hotels near Vermont Country Store
- Hotels with a Pool in Ludlow
- Hotels near Taylor Farm
- Hotels with Bars in Chester
- Hotel Wedding Venues Hotels in Brownsville
- Hotels with Bars in Springfield
- Golf Hotels in Bellows Falls
- 5 Star Hotels in Windham
- B&B in Bellows Falls
- Hotels with Hot Tubs in Springfield
- Flights to Ludlow
- Flights from Cavendish
- Flights to Brownsville
- Flights to Peru
- Flights from Hartness State
- Flights from Grafton
- Flights from Wisconsin Rapids (ISW) to Springfield (VSF)
- Flights from Newport News (PHF) to Springfield (VSF)
- Flights from Brownsville
- Flights from Springfield (SGF) to Springfield (VSF)
- Flights from Chester
- Flights from Ludlow
- Flights from Westminster
- Flights from Peru
- Flights from Ottawa (YOW) to Springfield (VSF)
- Flights from Raleigh (RDU) to Springfield (VSF)
- Flights to Windham
- Flights from Akulivik (AKV) to Springfield (VSF)
- Visit Central Vermont
- Visit Wilmington
- Visit Quechee
- Visit Gaysville
- Visit Killington
- Visit Arlington
- Fox Run Golf Course
- Visit Danby
- Visit Southern Vermont
- Visit Grafton
- Visit Saxtons River
- Weston Playhouse
- Visit Dorset
- Visit Perkinsville
- Visit West Dummerston
- Mount Ascutney
- Jud Hartmann Gallery
- Visit North Pomfret
- Visit Stockbridge
- Ball Mountain Dam
- Visit Jacksonville
- Grafton Ponds Outdoor Center
- Visit Landgrove
- Gallery North Star
- Visit Taftsville
- Visit Norwich
- Okemo Mountain Resort
- Visit Brownsville
- Vermont Country Store
- Visit Mount Tabor
- Lowell Lake State Park
- Visit Manchester Center
- Green Mountain Sugar House
- Visit Manchester
- Baltimore Covered Bridge
- Visit Weston
- Visit Mendon
- Visit Rupert
- Dorsey Park
- Visit Rockingham
- Visit East Dorset
- Jamaica State Park
- Visit Cavendish
- Visit Ludlow
- Enterprise Rental Cars in Weston
- Car rentals in National Car Rental 600 Rental Blvd
- Rental cars Hartness State airport
- Avis Rental Cars in Jamaica
- Car rentals near Townshend State Park
- Dollar Rent A Car Rental Cars in Peru
- Advantage Rent-A-Car Rental Cars in Peru
- Car rental Chester
- Car rental Brownsville
