Chester Vacation Packages

The team at Orbitz are keen to help you bundle up your hotels and flights to save cash. Simply choose an option and get packing for your dream trip to Chester.

Combining your bookings is one of the simplest ways to save. Select your desired airfares, hotels, rental cars and experiences to save as much as !

And remember — you have plenty of freedom. Customize your trip with 500 airline partners and no less than 500,000 worldwide hotels.

There are unlimited options to suit you and your individual style. All you have to do is decide on your package deal and get ready for an awe-inspiring escape!

Where is Chester?

Time to cross Chester off your map of the world?

If you take a trip 15 miles northeast of Claremont, or 30 miles north of Brattleboro, you'll end up in Chester.

Ready to meet some of the locals? 3,000 people call this part of Central Vermont- Killington home.

Car Rentals in Chester

Hi-ya, globetrotter. We know you want to squeeze the most out of your getaway, so why not check out car rentals in Chester? Book with Orbitz and get your epic adventure on the road today!File off the plane, get into a car and kick-start your adventure as soon as you arrive at Rutland Southern Vermont Regional Airport. You can pick up your rental at Enterprise, located at 131 S Main Street, 25 miles from the terminal.

Where to stay in Chester – Hotel Accommodation

Orbitz can help you reserve a comfortable room in this destination, but you'll have to act right away! At the moment, you'll find just 5 hotels in Chester.

Want us to make things easier? We suggest the Chester House Inn and Hugging Bear Inn and Shoppe.

Nearest Airports to Chester

If you're planning on flying in to Chester, you'll likely be touching down at Rutland Southern Vermont Regional Airport (RUT). Grab a coffee and find your bearings after disembarking your flight. This is the closest airport, sitting 25 miles away from the center of town.

Popular Places to Visit Near Chester

Checked out all the highlights in Chester itself? If you have a few more days on your hands, there's heaps more on offer in the surrounding area. You may not know that you're just 25 miles away from Bridgewater Corners. It's the perfect starting point to reach Killington Resort. This attraction is adored by locals and travelers alike.

No Cancellation Fees

Need to cancel or change your booking? Scared of a big fee? Well, you'll be glad to hear that we don't have one!^ All being well, your airline and hotel don't either, but it's a good idea to get in touch with them about their policies.