Book Hotels in Chester, VT
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Top Chester hotels

Woodstock Inn & Resort
Beautiful hotel with excellent staff and room cleanliness. Red Rooster Inn had good breakfast options, however dinner was a little underwhelming and expensive. There are better options at the local fine dining restaurants.
Reviewed on Oct 18, 2025

Kimpton Taconic Hotel by IHG
The is was our first trip to Manchester. What a great town! The hotel was lovely- easy parking, quiet, and quaint. The staff at the front desk were so helpful ! You could walk to town but it would be about a 20 min adventure… make sure you go to the North field book store~ wonderful!! And we had ...
Reviewed on Oct 12, 2025

The Shire Woodstock
Our room was clean and welcoming.
Reviewed on Oct 16, 2025

Pointe at Castle Hill Resort
Nice staff, clean room
Reviewed on Oct 18, 2025

Mountaineer Inn
Clean, quiet and safe. The only issue was finding parking spot in the premises at late night.
Reviewed on Oct 13, 2025

Jackson Gore Village
Property is great for kids. It is not within walking to any bars or restaurants, other than what they have on site. Staff are friendly, but they don't have daily housekeeping if that is important to you.
Reviewed on Oct 22, 2025

Keene Elm City Hotel, an Ascend Collection Hotel
Very nice & quiet. Close to downtown. Didn’t eat breakfast.
Reviewed on Oct 18, 2025

The Equinox Golf Resort & Spa
Stayed one night. Great location and beautiful resort hotel. Check in didn’t go well with 45 min delay. They gave us drink tickets and waived the resort fee. Other than that, great stay!
Reviewed on Oct 15, 2025

Days Inn by Wyndham Keene NH
We were lucky to find a room available anywhere in the area. Staff was pleasant. No tea/hot water available at breakfast. Did not notice that there was no elevator on the website, my fault for not reading better.
Reviewed on Oct 12, 2025
Cheap Chester hotels

Motel in the Meadow
Chester Hotel & Travel Guide\n
Are you intending on traveling in Central Vermont- Killington and looking to book lodgings around the Chester area? 7 hotels and apartments are within 6-mile (10-kilometer) of Chester and its surrounds.
Some of the more central Travelocity-listed hotels of downtown Chester are the Hugging Bear Inn and Shoppe and Fullerton Inn Bed & Breakfast.
Travelocity's extensive database offers only a limited number of economical hotel options in Chester. The Rose Arbour Bed & Breakfast is one of them.
The Castle Hill Resort And Spa is situated 9 miles (14 kilometers) outside of the main part of Chester. An alternative accommodation option is the Mountain Lodge at Okemo Mountain Resort, which is situated 12 miles (19 kilometers) away. Another possibility is to check out the rates and amenities at the Jackson Gore Inn or the The Andrie Rose Inn.
On your travels, why don't you check out some more of the forests and mountains that are commonly found in Central Vermont? Allow yourself to give yourself a few extra days in some other parts of Central Vermont. If you participate in common ways of enjoying yourself, such as snowboarding, skiing and cross-country skiing, or cross the region to see the landmarks, you'll be able to book the perfect Travelocity-registered lodgings in the local area.
Killington is 30 miles (45 kilometers) to the northwest of Chester and is home to Killington Ski Resort and Green Mountain National Golf Course. If you spend a few nights in Killington, be sure to check out the Killington Grand Resort Hotel and Mountain Green Ski & Golf Resort. Alternatively, you could stay in Rutland, 30 miles (49 kilometers) to the northwest of Chester, where you have the options of the Hampton Inn Rutland and Holiday Inn Rutland-Killington Area. The Pine Hill Park and Vermont State Fairgrounds are other frequented sites to visit should you visit Rutland.
Ensure a serving of sport by making a trek to Verizon Wireless Arena, which is 60 miles (97 kilometers) to the east of Chester. Travelers who like the thought of booking a room close to the stadium, book a room in the Hilton Garden Inn Manchester Downtown or Radisson Hotel Manchester Downtown.
After you have learnt a little about the Travelocity-listed accommodation options in Chester, take the time to browse our Chester travel page for local secrets on all the scenic and cultural attractions in this corner of the world.
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Jackson Gore Village
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