Chester Vacations from $1,013
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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.
Good Hotels Boston
South End
Save 100% on your flight
Price was $1,755, price is now $1,013 per person
$1,013
per person
Sep 25 - Sep 28
found 24 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8/10 Very Good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.
Reviewed on May 23, 2026
Boston Lodge and Suites
Dorchester
Save 100% on your flight
Price was $2,321, price is now $1,308 per person
$1,308
per person
Sep 3 - Sep 10
found 5 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
The Coach House
Save 100% on your flight
Price was $1,891, price is now $1,178 per person
$1,178
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (182 reviews)
This experience was amazing! We loved every detail. It was so trendy and dapper yet held the boldness with such grace. It was lovely. The room had everything to make your stay comfortable. There was coffee and teas and fresh water. We found this refreshing on the hot summer day that we were there. The beds were so nice. The snacks and robes were a great touch.
We loved reading about the history and just adored everything.
Reviewed on Jul 11, 2026
By the Sea Guests Bed & Breakfast & Suites
Save 100% on your flight
Price was $2,310, price is now $1,469 per person
$1,469
per person
Sep 3 - Sep 10
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (195 reviews)
The staff here was so kind and thoughtful. The breakfast was amazing all 3 days and the beach was very quiet and great waterfront. The section we stayed has not been updated like some of the other units but was fine and comfortable. The general location was good and easily walkable to food and drink places. Overall, we enjoyed it and would stay here again for sure.
Reviewed on Jul 12, 2026
Stay near popular Chester attractions
Chester Hotel Deals
La Quinta Inn & Suites by Wyndham Boston-Andover
131 River Rd Andover MA
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $130 total per night from Jul 20 to Jul 21
$130 total
Jul 20 - Jul 21
Total with taxes and fees
8.2/10 Very Good! (2,110 reviews)
"The client next door had a Dog that wouldn’t stop barking it was 8am and the Dog was non stop barking wouldn’t recommend anybody of you want a relax and stay at a moment of piece and quiet."
Reviewed on Jul 12, 2026
Best Western Plus Executive Court Inn & Conference Center
13500 S Willow St Manchester NH
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $108 total per night from Jul 19 to Jul 20
$108 total
Jul 19 - Jul 20
Total with taxes and fees
8.2/10 Very Good! (1,407 reviews)
"Waited almost 15 minutes to check in because the front desk staff were not present. Also, the floor in the room as dirty because my white socks are black on the bottom. The sink drained super slow, lightbulb above the hot tub in the room was flickering bad and the room is overdue for a face lift. ..."
Reviewed on Jul 12, 2026
La Quinta Inn & Suites by Wyndham Salem NH
8 Keewaydin Dr Salem NH
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $103 total per night from Aug 2 to Aug 3
$103 total
Aug 2 - Aug 3
Total with taxes and fees
8.4/10 Very Good! (1,279 reviews)
"Clean room and nice environment"
Reviewed on Jul 13, 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.
