Chester Vacations from $575
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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.
Sea Crest Beach Resort
Price was $816, price is now $575 per person
$575
per person
May 22 - May 26
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8/10 Very Good! (259 reviews)
The staff were really nice and the food was good. They have an excellent location right on the beach.
Reviewed on Mar 12, 2026
The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was $2,068, price is now $1,454 per person
$1,454
per person
May 14 - May 17
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (1,000 reviews)
The rooms were very clean, beds were comfortable, staff friendly and great amenities (I wish the pool was open until 10 pm).
Reviewed on Apr 4, 2026
The Westin Waltham-Boston
Price was $1,196, price is now $847 per person
$847
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8.8/10 Excellent! (1,092 reviews)
Great hotel and location. Rooms were a bit old but excellent location and condition.
Reviewed on Apr 9, 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! (1,003 reviews)
Great service
Reviewed on Apr 8, 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 14 to Apr 15
$80 total
Apr 14 - Apr 15
Total with taxes and fees
8.4/10 Very Good! (1,152 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.
