
Chester Vacations from $345
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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 Inn at Hastings Park, Relais & Chateaux - Boston
Price was $1,942, price is now $771 per person
$771
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (245 reviews)
Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room.
Reviewed on Oct 21, 2025

Raffles Boston
Back Bay
Price was $980, price is now $490 per person
$490
per person
Dec 29 - Jan 1
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (169 reviews)
Overall, my husband & I enjoyed our stay at the Raffles -- but we weren't thrilled with the level of service we received. Specifically:
- We checked in late (~11pm) due to a train delay, and the front desk informed us that our "butler" would reach out the next morning to introduce various services, etc. That never happened, which was disappointing because butler service is a Raffles staple that we were looking forward to experiencing.
- Upon getting to our room, which was otherwise lovely, it became clear that the touchscreen-enabled lighting system had malfunctioned. This meant we could only have ALL the lights in the room (+ bathroom) 100% on or 100% off -- no in-between (and no dimming, etc). I alerted the front desk immediately, who offered to send an engineer "within an hour or so" -- but at that point it was nearly 12am, and we were too exhausted to wait so we declined. No one ever followed up with us or offered a solution to the issue, which grew increasingly annoying throughout our stay (e.g., I had to use my phone light to use the bathroom at night because the only other option would have been to turn ALL of the lights on 100% (and wakeup my husband). The issue also extended to the "request service" vs. "privacy please" button, so we had no way of requesting (or denying) maid service.
- My husband & I celebrated our anniversary on this trip, and I let the hotel know in advance (hoping for at least a card or little treat) -- but this went 100% unacknowleged.
Reviewed on Oct 20, 2025

The Whitney Hotel
Beacon Hill
Price was $840, price is now $438 per person
$438
per person
Dec 29 - Jan 1
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (475 reviews)
Love to the room, it was perfect for what we needed. Excellent service and excellent location. We will definitely stay here again.
Reviewed on Oct 13, 2025

The Newbury Boston
Back Bay
Price was $1,412, price is now $763 per person
$763
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (522 reviews)
Great location but they have no concierge , and for the price you will think they would. Rooms are small
Reviewed on Oct 8, 2025
Chester Hotel Deals

Methuen Inn and Conference Center
159 Pelham Street, Methuen, MA
Fully refundable
$97 nightly
The price is $108 total per night from Oct 26 to Oct 27
$108 total
Oct 26 - Oct 27
Total with taxes and fees
6.2/10 (1,061 reviews)
Conveniently right next to the interstate.
Reviewed on Oct 22, 2025

DoubleTree by Hilton Manchester Downtown
700 Elm St., Manchester, NH
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $133 total per night from Oct 26 to Oct 27
$133 total
Oct 26 - Oct 27
Total with taxes and fees
9/10 Wonderful! (1,048 reviews)
Great location, great friendly service. Good free lobby coffee!
Reviewed on Oct 20, 2025

Park View Inn - Salem
109 S Broadway, Salem, NH
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $100 total per night from Nov 23 to Nov 24
$100 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (1,530 reviews)
Really peaceful and pretty, cozy, employees very nice amenities, location, price everything, one of my new favorite places to stay.
Reviewed on Oct 21, 2025
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.