Name: The Shire Woodstock
Rating: 8.6

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

SAR 522

SAR 569 total

3 Sep - 4 Sep

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 ...

8/10 Very Good! (371 reviews)

Great Inn in a quaint town.

"A wonderful little Inn with such a pleasant owner and just a great vibe there. Would absolutely recommend for a summer or winter stay. Can imagine it is beautiful in the winter."

Reviewed on 3 August 2025

Woodstock Inn & Resort

Fourteen The Green, Woodstock, VT

SAR 1,535

SAR 1,853 total

2 Sep - 3 Sep

includes taxes & fees

Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...

9.2/10 Wonderful! (531 reviews)

"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on 30 July 2025

The Shire Woodstock

46 Pleasant St., Woodstock, VT

Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...

8.6/10 Excellent! (807 reviews)

"Forth time at The Shire, everything was wonderful!!"

Reviewed on 21 August 2025

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See all 2,951 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

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! (23 reviews)

Hidden gem!

"This lovingly built off-grid glamping cabin is drenched with sun! It’s absolutely gorgeous! The kids enjoyed pumping their own water and sledding down the front hill. Paris is an excellent hostess- she answered all our questions very promptly & thoroughly. We cant wait to come back! Thank you!!!"

Reviewed on 24 February 2025

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3387 East Mountain Road, Killington, VT

Stay at this 3-star ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage ...

8.8/10 Excellent! (47 reviews)

"Great value, comfortable space, responsive host!"

Reviewed on 13 August 2025

Idyllic Lakefront House Suited Two Families

Ludlow

Book a stay at this family-friendly vacation home in Ludlow. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Okemo Mountain Resort and ...

9.6/10 Exceptional! (150 reviews)

"House and grounds were well maintained."

Reviewed on 11 August 2025

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.

Check Chester hotel availability

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.

Chester, VT

Travel Guide

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