Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Collect Nectar points
Collect Nectar points
Collect Nectar points
Free cancellation

Explore Chester

Explore Chester with Expedia’s Travel Guides to find the best hotels, flights, holiday packages and more!

Expedia car hire in Chester comes with No Hidden Fees

Why rent a car in Chester?

Describing itself as ‘the Vermont you’ve been hoping to find’, Chester is a charming New England town in the scenic area of Windsor County. Chester is the ideal place to exploring the stunning sights of Vermont by hire car.

How to get to and around Chester?

If you’re arriving in Chester via Rutland Southern Vermont Regional Airport, then it’s a 31-mile drive by rental car into the town. En route you can visit Okemo State Forest, one of Vermont’s biggest areas of woodland with wildlife that includes deer, bear and moose.

What brands are available?

There are various hire car providers to suit your budget and preferences, including Budget, Dollar and Alamo. Many offer extras like free cancellation, unlimited mileage and shuttle services to your rental car.

Must-sees within an easy drive of Chester

Nestled in the Vermont landscape, Chester has a charming bygone era feel. The town is filled with art galleries, antique stores and a range of restaurants, and also contains a historic ‘stone village’ of pre-Civil War houses.

Named after President Lincoln, Mount Abraham is the tallest mountain in Vermont and is an 85-mile drive by rental car from Chester. Vermont’s capital, Montpelier, is a 98-mile drive away and includes attractions like the gold-domed capital building of Vermont State House, the Fairbanks Museum and Planetarium, and Bragg Farm Sugarhouse and Gift Shop, a family maple farm that’s open to visitors.

Lake Champlain, a 141-mile journey away, is a beautiful body of water that’s the sixth largest in the US. It has 200 miles of shoreline and is scenic to explore by hire car.

Tips and tricks for driving in Chester

Due to its mountains and forests, Vermont is stunning to explore by rental car, especially in autumn. When driving through rural areas, keep an eye out for wildlife such as deer and also take care in snowy conditions. Remember that the US is right-hand drive and also keep an eye on your mirror, as drivers don’t always indicate a direction change. Every state has different driving laws, so make sure you familiarise yourself with the Vermont ones before your visit.

Ready to plan your Chester city break?

Feeling inspired to explore Chester and the rest of Vermont? Check out this Holiday Guide and use the Expedia search tool to help you find the best car hire, flight and hotel deals and to research the best attractions and activities.

Remember that Expedia car hire comes with no hidden fees. The price you see is the price you pay!