
Chester Vacation Packages
Book a Stay + Flight or Car to save on your trip
Chester Vacation Package Deals
One-stop vacation shopping with Orbitz will give you direct access to Chester packages from $673, but the real beauty of a package vacation is that Orbitz does all the searching for you.
Gone are the days of hunting for a flight and hotel separately, comparing hundreds of flight sales and hotel deals, with the added pressure of keeping track of all those pesky reference numbers. Check out an all-inclusive resort hotel package, where the price will also cover your food, drink, and activities, or a simple flight and hotel package, and enjoy the luxury of having all your essential information in one place.
Whether you’re planning on visiting Chester in peak season () or you want to avoid the crowds and go during the quieter months (), you can customize your package to your own unique travel needs.
Don’t forget to join Orbitz Rewards and start earning Orbucks to spend on bookings for over 350,000 hotels across the world. For each dollar you spend, you instantly earn 1 Orbuck, which you can redeem at your convenience. Being an Orbitz Reward member also means you get access to exclusive deals with Insider Prices as well as VIP Hotel benefits and upgrades.
When you book a package deal with Orbitz, not only are you in for a quick and easy booking process, but you also get the chance to make some great savings. And since the flight and hotel are paid for upfront and in one place, managing your budget will be a breeze.
Top Chester vacation package deals

Hearthstone Inn Boutique Hotel Halifax - Dartmouth
Nov 19 - Nov 24
Boston (BOS) to Halifax (YHZ)
Halifax (YHZ) to Boston (BOS)
Reviewed on Aug 21, 2024

Inn on the Lake
Nov 19 - Nov 24
Boston (BOS) to Halifax (YHZ)
Halifax (YHZ) to Boston (BOS)
Reviewed on Aug 4, 2024

Chateau Bedford, Trademark Collection by Wyndham
Nov 19 - Nov 24
Boston (BOS) to Halifax (YHZ)
Halifax (YHZ) to Boston (BOS)
Reviewed on Mar 9, 2025

Lux Exec Home HFX Waterfront Pool Hot Tub
Nov 19 - Nov 24
Boston (BOS) to Halifax (YHZ)
Halifax (YHZ) to Boston (BOS)
Top rated hotels for your Chester vacation package

Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

Moonlight Cottage

Future Inns Halifax
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