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
$139 nightly
The price is $152 total per night from Sep 1 to Sep 2
$152 total
Sep 1 - Sep 2
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 ...
8/10 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 Aug 3, 2025
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
$449 nightly
The price is $494 total per night from Sep 1 to Sep 2
$494 total
Sep 1 - Sep 2
Total with taxes and 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 Jul 30, 2025
The Shire Woodstock
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $204 total per night from Aug 28 to Aug 29
$204 total
Aug 28 - Aug 29
Total with taxes and fees
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 Aug 21, 2025
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 Feb 24, 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 Aug 13, 2025
Owl's Nest Treehouse
Alstead
Stay at this cabin in Alstead. Enjoy cable/satellite TV service, an in-room coffeemaker, and air conditioning. Popular attractions Shedd-Porter Memorial Library ...
10/10 Exceptional! (7 reviews)
MAGICAL!
"My husband and I stayed two nights to celebrate our 10th wedding anniversary. From start to finish, this trip was amazing. The treehouse was tucked back into the woods with plenty of privacy. The pathway lights and the lanterns surrounding the lower deck area was gorgeously inviting. We made our ..."
Reviewed on Aug 8, 2025
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
- Killington Resort
- Okemo Mountain Resort
- Stratton Mountain Resort
- Mount Snow
- Green Mountain National Forest
- Bromley Mountain Ski Resort
- Magic Mountain Ski Resort
- Keene State College
- Golf Club at Equinox
- Vermont Country Store
- Connecticut River
- Equinox Preservation Trust
- Stratton Mountain Summit Gondola
- Billings Farm and Museum
- Hildene
- Mount Snow Golf Course
- Landmark College
- Manchester Designer Outlets
- Connecticut Lakes Region
- Mt Ascutney State Park
- American Express Ski Lift
- Historic Main Street
- Spofford Lake
- Blow-Me-Down Bridge
- Emerald Lake State Park
- Lake Rescue
- Colonial Theatre
- Sunrise Village Triple Ski Lift
- Molly Stark State Park
- Battenkill River