Chester Vacations from $591
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Your Chester Vacation
With plenty of highlights as well as some hidden gems, this city is best explored with a Chester vacation package. Find a place to stay in Downtown Manchester, which is great for cafes, history and bars and pubs. There's plenty to see and do during your trip to Chester, including Zorvino Vineyards and Robert Frost Farm State Historic Site. No matter your travel plans or the size of your budget, organizing your ultimate tailored Chester vacation is a cinch with Expedia.
The Latest Chester vacation packages
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Boston
Bay Village
$1,271
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (487 reviews)
For the most high end hotel in Boston, lacked updated amenities that other newer hotels have. Rooms were severely dated.
Reviewed on Oct 20, 2026
Stay near popular Chester attractions
Chester Town Hall
After visiting Chester Town Hall, make a plan to see the other sights and activities in Chester.
Chester Public Library
Chester Public Library is just one of the places to see in Chester, so why not enjoy the other things to explore during your travels?
Chester Hotel Deals
Methuen Inn and Conference Center
159 Pelham Street Methuen MA
Fully refundable
$103 nightly
$115 total
Oct 25 - Oct 26
Total with taxes and fees
6/10 (1,033 reviews)
"Furnishings were extremely old. Drapery had holes from how old they were. Sheets were stained. The room smelled like old"
Reviewed on Oct 23, 2026
DoubleTree by Hilton Boston - Andover
123 Old River Rd Andover MA
Fully refundableReserve now, pay when you stay
$122 nightly
$137 total
Nov 6 - Nov 7
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Boston-Andover
131 River Rd Andover MA
Fully refundableReserve now, pay when you stay
$106 nightly
$119 total
Nov 22 - Nov 23
Total with taxes and fees
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.
Find the Best Chester Vacation Packages
Chester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Manchester-Boston Regional Airport (MHT) |
Population | 5,200 |
Top Sights | Canobie Lake Park, Bear Brook State Park and Zorvino Vineyards |
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Frequently asked questions
How much does a Chester vacation package cost?
You'll find cheap prices from $591 on Expedia for your Chester escape. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Chester costs.
What are the cheapest months to go to Chester?
If you're looking to score a cheap Chester vacation package, consider visiting in October, November and December. You'll typically find lower rates on hotels and airfares during these months — ideal for a budget-friendly getaway.
How many days is enough for Chester?
Generally, a handful of days is enough to check out the top sights during your Chester vacation. But if you prefer to have more time to unwind or take day trips, think about extending your itinerary.
How to find the best Chester package deals?
Use Expedia's filter tool to help you find some great Chester package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Chester package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Chester vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component separately. And you'll still have the freedom to create a customized Chester vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Chester?
If you've got your Chester vacation dates locked in, book as soon as you can to grab some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
Your Chester trip should be an escape from your busy life, not a source of money worries. So to allow you more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
