Chester Vacations from $363

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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 Cove At Yarmouth

The Cove At Yarmouth

3 out of 5
Save 100% on your flight
Price was $587, price is now $363 per person
$363
per person
Feb 19 - Feb 23
found 8 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Boston (BOS)
9.2/10 Wonderful! (243 reviews)
The unit on or suite units are on second floor with no elevator. In addition, the bedroom is on another level. For those with physical issues only.insist on first floor I found 1st floor bath dirty. This is a time share rental which suits families with young kids.

Reviewed on Oct 6, 2025

DoubleTree by Hilton Manchester Downtown

DoubleTree by Hilton Manchester Downtown

4 out of 5
Downtown Manchester
Save 100% on your flight
Price was $545, price is now $364 per person
$364
per person
Jan 26 - Jan 31
found 14 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Boston (BOS)
9/10 Wonderful! (1,061 reviews)
Rooms clean, staff nice, good location

Reviewed on Dec 14, 2025

The Centennial

The Centennial

4 out of 5
Save 100% on your flight
Price was $613, price is now $416 per person
$416
per person
Jan 26 - Jan 31
found 14 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Manchester (MHT)
8.8/10 Excellent! (1,000 reviews)
Room was cleaned but maybe not used in a while so dusty

Reviewed on Dec 10, 2025

citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
Fenway–Kenmore
Save 100% on your flight
Price was $556, price is now $381 per person
$381
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Boston (BOS)
9.4/10 Exceptional! (2,013 reviews)
Always enjoy staying there

Reviewed on Dec 13, 2025

Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

3.5 out of 5
Newton Corner
Save 100% on your flight
Price was $718, price is now $500 per person
$500
per person
Feb 10 - Feb 15
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
8.4/10 Very Good! (2,907 reviews)
Signage to get to it is horrible!

Reviewed on Dec 12, 2025

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Chester Hotel Deals

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
$104 nightly
The price is $117 total per night from Dec 22 to Dec 23
$117 total
Dec 22 - Dec 23
Total with taxes and fees
8/10 Very Good! (1,939 reviews)
Yes

Reviewed on Dec 9, 2025

La Quinta Inn & Suites by Wyndham Boston-Andover
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
$114 nightly
The price is $124 total per night from Jan 4 to Jan 5
$124 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9/10 Wonderful! (1,085 reviews)
Nice clean room,comfortable bed,nice lounge

Reviewed on Dec 15, 2025

DoubleTree by Hilton Manchester Downtown
Park View Inn - Salem

Park View Inn - Salem

2 out of 5
109 S Broadway Salem NH
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $85 total per night from Dec 21 to Dec 22
$85 total
Dec 21 - Dec 22
Total with taxes and fees
8.6/10 Excellent! (1,595 reviews)
Friendly staff, clean and tidy.

Reviewed on Dec 10, 2025

Park View Inn - Salem
See all 473 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 $363 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.