Chester, VT

Name: On The River Inn
Price range: $274 total

Travel Guide

A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Visit Chester

Where to stay in Chester

Find the best Chester areas and neighborhoods for the activities you enjoy most. Learn more about Chester

Chester Depot

A forest with autumn foliage in various colors.

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

$449 nightly

$494 total

Sep 7 - Sep 8

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! (599 reviews)

"Amazing! Will visit again."

Reviewed on Aug 7, 2026

Kimpton Taconic Hotel by IHG

3835 Main St. Manchester VT

$257 nightly

$283 total

Sep 9 - Sep 10

Total with taxes and 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 Aug 17, 2026

On The River Inn

1653 West Woodstock Road Woodstock VT

$249 nightly

$274 total

Sep 8 - Sep 9

Total with taxes and 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 ...

See all 3,094 properties in Chester

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! (25 reviews)

"This is an adorable and cozy cabin surrounded by nature - from which you can hear a soothing stream from your window. If you are looking for a place to restore in nature and unplug "glamping-style" - yet close to shops/coffee/outings, etc., - this little blue cabin is the perfect spot. I liked that ..."

Reviewed on Jul 6, 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 ...

9.2/10 Wonderful! (67 reviews)

"Nice area, clean and kitchen was well equipped. We used the air fryer for dinner one night."

Reviewed on Aug 15, 2026

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Cavendish VT

Stay at this cabin in Cavendish. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Phineas Gage Memorial and Mount Ascutney are located ...

10/10 Exceptional! (53 reviews)

"The cabins are a great getaway, stocked with everything you need for a comfortable stay in the woods. They have nice kitchens and comfortable beds, heat and AC, outdoor grills and firepits. The hot tub is a great way to relax after a day of hiking or skiing."

Reviewed on Aug 24, 2026

See all properties in Chester

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.