Chester Vacations from $178

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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.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Save 100% on your flight
Price was $297, price is now $178 per person
$178
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,173 reviews)
Room was just big enough and clean. A bit noisy but hey it’s downtown Boston what can you expect. No VIP upgrades or drink vouchers were given. Bathroom sharing was fine but some people have the bathrooms pretty messy with their towels and stuff. Convenient location nice staff.

Reviewed on Nov 11, 2025

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $306, price is now $179 per person
$179
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,830 reviews)
Slight issue with online check in. Person on the desk was great and all sorted

Reviewed on Nov 11, 2025

The Bostonian Boston

The Bostonian Boston

4 out of 5
Government Center
Save 100% on your flight
Price was $373, price is now $220 per person
$220
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (1,952 reviews)
Great location. Room was clean and comfortable, but hotel is in need of a remodel.

Reviewed on Nov 11, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Save 100% on your flight
Price was $332, price is now $196 per person
$196
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.8/10 Excellent! (2,117 reviews)
Room was clean when we got there. We stayed there 4 nights and everyday they fixed our beds, took out trash and brought clean towels. Breakfast was also delicious.

Reviewed on Nov 11, 2025

Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Bay Village
Save 100% on your flight
Price was $395, price is now $248 per person
$248
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.8/10 Excellent! (1,910 reviews)
Great hotel experience

Reviewed on Nov 10, 2025

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Chester Hotel Deals

DoubleTree by Hilton Manchester Downtown

DoubleTree by Hilton Manchester Downtown

4 out of 5
700 Elm St., Manchester, NH
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $121 total per night from Nov 27 to Nov 28
$121 total
Nov 27 - Nov 28
Total with taxes and fees
9/10 Wonderful! (1,060 reviews)
Front desk staff very helpful and courteous, room very spacious, clean and comfortable

Reviewed on Nov 8, 2025

DoubleTree by Hilton Manchester Downtown
DoubleTree by Hilton Boston - Andover

DoubleTree by Hilton Boston - Andover

4 out of 5
123 Old River Rd, Andover, MA
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $110 total per night from Dec 4 to Dec 5
$110 total
Dec 4 - Dec 5
Total with taxes and fees
8/10 Very Good! (1,004 reviews)
Nice pillows! In room coffee station. was not supplied with creamer. Ladder on pool was broken.

Reviewed on Nov 4, 2025

DoubleTree by Hilton Boston - Andover
La Quinta Inn & Suites by Wyndham Boston-Andover

La Quinta Inn & Suites by Wyndham Boston-Andover

3 out of 5
131 River Rd, Andover, MA
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $122 total per night from Nov 13 to Nov 14
$122 total
Nov 13 - Nov 14
Total with taxes and fees
8/10 Very Good! (1,908 reviews)
Clean room , nice staff . Great restaurant you can walk to

Reviewed on Nov 10, 2025

La Quinta Inn & Suites by Wyndham Boston-Andover
See all 486 properties in Chester
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 $178 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.