Chester Vacations from $561
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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.
D. Hotel Suites & Spa
Save 100% on your flight
Price was $893, price is now $561 per person
$561
per person
Jun 21 - Jun 26
just found
Roundtrip flight included
Minneapolis (MSP) to Boston (BOS)
9.4/10 Exceptional! (2,227 reviews)
We have been here multiple times and always have a great stay! Rooms were clean. Pool and hot tub were great and staff were consistently checking the water conditions.
Reviewed on Apr 12, 2026
Eurostars The Boxer
West End
Save 100% on your flight
Price was $3,336, price is now $1,935 per person
$1,935
per person
Jun 12 - Jun 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.8/10 Excellent! (1,426 reviews)
Everything advertised was correct and enjoyable relaxing.
Reviewed on Apr 11, 2026
The Westin Boston Seaport District
Seaport District
Save 100% on your flight
Price was $2,146, price is now $1,270 per person
$1,270
per person
Jun 12 - Jun 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (2,398 reviews)
The beds were small. They were double beds. Other than that everything was perfect.
Reviewed on Apr 12, 2026
The Wylie Inn and Conference Center at Endicott College
Save 100% on your flight
Price was $1,487, price is now $899 per person
$899
per person
Jun 21 - Jun 26
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (1,173 reviews)
Yes. Great location and the facilities are top notch with wonderful staff
Reviewed on Apr 10, 2026
Chester Hotel Deals
DoubleTree by Hilton Manchester Downtown
700 Elm St. Manchester NH
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $133 total per night from Apr 19 to Apr 20
$133 total
Apr 19 - Apr 20
Total with taxes and fees
9.2/10 Wonderful! (1,163 reviews)
Restaurants food was good
Reviewed on Apr 8, 2026
DoubleTree by Hilton Boston - Andover
123 Old River Rd Andover MA
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $123 total per night from May 1 to May 2
$123 total
May 1 - May 2
Total with taxes and fees
8.2/10 Very Good! (1,006 reviews)
We were on the first floor and the people in the room above us were making noise the entire night. Like, really loud noise; they were learning River Dance, practicing their WWE moves, or committing a crime, not sure which. This went on until about 3:30 in the morning.
Reviewed on Apr 12, 2026
La Quinta Inn & Suites by Wyndham Salem NH
8 Keewaydin Dr Salem NH
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $80 total per night from Apr 15 to Apr 16
$80 total
Apr 15 - Apr 16
Total with taxes and fees
8.4/10 Very Good! (1,154 reviews)
The room was very clean; the only drawback was that the bed was too soft.
Reviewed on Apr 9, 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
