Chester Vacations from $230

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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 $363, price is now $230 per person
$230
per person
Mar 18 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,241 reviews)
Excellent value for the price. The lobby was well decorated. Would love to stay again.

Reviewed on Jan 7, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $986, price is now $582 per person
$582
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (247 reviews)
Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room.

Reviewed on Oct 21, 2025

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $436, price is now $271 per person
$271
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (2,242 reviews)
Nice room with separate living room. We enjoyed the gym, pool and hot tub. We stayed on second floor and there is only one elevator, so you have to wait sometime. I wish there is stairs to walk down.

Reviewed on Jan 6, 2026

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $846, price is now $562 per person
$562
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Such a warm and cozy place with great amenities!

Reviewed on Dec 31, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,030, price is now $688 per person
$688
per person
Apr 2 - Apr 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Beautiful property and room.

Reviewed on Jan 8, 2026

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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
$122 nightly
The price is $133 total per night from Jan 12 to Jan 13
$133 total
Jan 12 - Jan 13
Total with taxes and fees
9/10 Wonderful! (1,107 reviews)
Good for price

Reviewed on Jan 8, 2026

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
$99 nightly
The price is $111 total per night from Feb 1 to Feb 2
$111 total
Feb 1 - Feb 2
Total with taxes and fees
8/10 Very Good! (1,972 reviews)
Every thing is good

Reviewed on Jan 5, 2026

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
$78 nightly
The price is $85 total per night from Jan 11 to Jan 12
$85 total
Jan 11 - Jan 12
Total with taxes and fees
8.6/10 Excellent! (1,629 reviews)
Staff was excellent. Room was excellent. Happy that it was a 1 floor hotel. Location was near shopping.

Reviewed on Jan 6, 2026

Park View Inn - Salem
See all 485 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 $230 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.