Chester Vacations from $586
Book a Hotel + Flight or Car together to unlock savings
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.
Boston Lodge and Suites
Dorchester
$586
per person
Nov 3 - Nov 7
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
Stay near popular Chester attractions
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 Town Hall
After visiting Chester Town Hall, make a plan to see the other sights and activities in Chester.
Chester Hotel Deals
La Quinta Inn & Suites by Wyndham Boston-Andover
131 River Rd Andover MA
Fully refundableReserve now, pay when you stay
$116 nightly
$130 total
Aug 30 - Aug 31
Total with taxes and fees
Lamie's Inn and The Old Salt Restaurant
490 Lafayette Rd Hampton NH
Fully refundableReserve now, pay when you stay
$110 nightly
$119 total
Sep 1 - Sep 2
Total with taxes and fees
9.4/10 Exceptional! (1,005 reviews)
"The place is very clean and very pleasant. The continental breakfast was delicious with a lot of options. Staff is helpful and nice. My only complain is that the walls are paper thon and you can hear everything. We were unlike to be next to a room were the guest were drunk and loud and we could hear ..."
Reviewed on Aug 27, 2026
Comfort Inn Manchester Airport
298 Queen City Ave Manchester NH
Fully refundable
$86 nightly
$94 total
Sep 6 - Sep 7
Total with taxes and fees
8.4/10 Very Good! (1,008 reviews)
"Good room for the price"
Reviewed on Aug 29, 2026
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 $586 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.