Chester, VT

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.

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
A forest with autumn foliage in various colors.

Chester Depot

If you're spending some time in Chester Depot, Bonnie's Bundles Dolls and DaVallia Art & Accents are top sights worth seeing.

Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common Chester VT
$129 nightly
The price is $141 total per night from Nov 9 to Nov 10
$141 total
Nov 9 - Nov 10
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 ...
Fullerton Inn
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
698 VT-11 Chester VT
$269 nightly
The price is $294 total per night from Oct 21 to Oct 22
$294 total
Oct 21 - Oct 22
Total with taxes and fees
Stay at this B&B in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (130 reviews)
"Breakfast was very nice and staff very friendly… unfortunately it is not very accessible if you have walking difficulties … all the bedrooms are on the second floor and there are no elevators… l wish l had known this before l had booked the room …. we stayed 1 night even though we had reserved 2 ..."

Reviewed on Oct 8, 2026

Stone Hearth Inn and Eatery
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

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

Get rates
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
See all 3,116 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

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

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
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! (69 reviews)
"Property was good. We founded a lot of cobble webs around the house. The stove was dirty when we used and made a horrible smell of burned. The guys next door were very loud at 3am and we couldn't sleep till they left around 5-6am. Will for sure be back if we have a chance. The place is well located ..."

Reviewed on Oct 5, 2026

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Ludlow VT
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! (146 reviews)
"Great cabin in the pines. Host very communicative and answered all our questions with good response time. Property was clean and well maintained. Definitely would book this one again!"

Reviewed on Sep 25, 2026

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
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.

Stay near popular Chester attractions

Bonnie's Bundles Dolls

7.6/10 (4 reviews)
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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Frequently asked questions

Is Chester worth visiting?
Chester is worth visiting for its diverse dining scene, offering both Italian and North American cuisine. Travelers can also discover unique local attractions such as DaVallia Art & Accents, showcasing art, and Bonnie's Bundles Dolls, for those interested in collectibles.
When is the best time to visit Chester?
The best time to visit Chester is from May through September, when the weather is generally pleasant for exploring. For fewer crowds and better value, the quieter months of November through February are a good bet, offering a different, calmer experience with cooler temperatures.
What is Chester known for?
Chester is known for being home to unique shops such as DaVallia Art & Accents and Bonnie's Bundles Dolls. Travelers can also enjoy the local Italian food culture, making it a pleasant destination for those seeking arts and good cuisine.
What is a good itinerary length for Chester?
A good itinerary length for Chester is one day to explore unique spots like DaVallia Art & Accents and Bonnie's Bundles Dolls. For a slightly longer visit, perhaps two days, travelers can enjoy the local Italian, North American, and Asian dining options, making for a relaxed short trip.
What are the top things to do in and around Chester?
In Chester, travelers can explore local points of interest such as DaVallia Art & Accents and Bonnie's Bundles Dolls.
What cuisines can you find in Chester?
In Chester, travelers can find Mexican cuisine, with dishes like tacos, burritos, and enchiladas. You can also enjoy Italian fare, North American options such as Southern soul food and New American dishes, and a variety of Asian choices including Chinese, Japanese, and Thai. Mediterranean and South American flavors are also available.
Can I book a refundable hotel in Chester?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Chester by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Chester with Expedia?
Expedia makes it easier to plan your Chester trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Chester?
The best choice depends on your travel style. Hotels in Chester can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Chester trip on Expedia?
Once you've booked your Chester trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Chester trip?
Expedia offers customer support before, during, and after your Chester trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Chester?
If it's your first trip to Chester, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Chester hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Chester hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Chester

A calm lake reflecting a forest with autumn foliage.

Bellows Falls

A street with historic buildings, including a diner and a Blue Star Trading Company.

Ludlow

A town square with historic buildings, a crosswalk, and a street lined with parked cars.

Springfield

A snow-covered landscape with a bench and trees.

Londonderry

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