Chester Vacations from $330

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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.
Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor

4 out of 5
East Boston
Save 100% on your flight
Price was $585, price is now $330 per person
$330
per person
Jan 8 - Jan 13
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (1,732 reviews)
Everything was great there! I added this hotel to my personal STAY AT list 😊

Reviewed on Nov 26, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was $1,360, price is now $718 per person
$718
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Clean room, staff is nice and helpful

Reviewed on Nov 29, 2025

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $800, price is now $442 per person
$442
per person
Jan 8 - Jan 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
Clean room, nice staff

Reviewed on Nov 30, 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $1,610, price is now $941 per person
$941
per person
Jan 2 - Jan 7
just found
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (536 reviews)
This hotel has it all, best in class care and service.

Reviewed on Oct 24, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $1,643, price is now $962 per person
$962
per person
Feb 11 - Feb 16
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
Phenomenon phenomenon will definitely will be back

Reviewed on Nov 26, 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
$114 nightly
The price is $124 total per night from Dec 4 to Dec 5
$124 total
Dec 4 - Dec 5
Total with taxes and fees
9/10 Wonderful! (1,078 reviews)
Clean room very friendly staff, very convenient to the SNHU arena. Highly recommend

Reviewed on Nov 30, 2025

DoubleTree by Hilton Manchester Downtown
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
$105 nightly
The price is $118 total per night from Dec 3 to Dec 4
$118 total
Dec 3 - Dec 4
Total with taxes and fees
8/10 Very Good! (1,929 reviews)
Everything

Reviewed on Nov 27, 2025

La Quinta Inn & Suites by Wyndham Boston-Andover
Park View Inn - Salem

Park View Inn - Salem

2 out of 5
109 S Broadway Salem NH
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $86 total per night from Dec 31 to Jan 1
$86 total
Dec 31 - Jan 1, 2026
Total with taxes and fees
8.6/10 Excellent! (1,587 reviews)
Friendly staff, clean room. Recommend.

Reviewed on Nov 29, 2025

Park View Inn - Salem
See all 469 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 $330 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.