
Chester Vacation Packages
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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.
Top Chester Vacation Deals
Price found within the past 48 hours. Click for updated prices.

The Inn at Hastings Park, Relais & Chateaux - Boston
Save 100% on your flight
per person
Aug 29 - Sep 1
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)
Reviewed on Jun. 6, 2025


Doubletree By Hilton Boston Logan Airport Chelsea
Save 100% on your flight
per person
Aug 1 - Aug 8
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very Good! (1,475 reviews)
I do not have any problem with the property especially my room it’s spacious, modern and the bed is comfortable. It’s very near the airport with free shuttle every 30 minutes. You can walk from the hotel going to Burger King, grocery, TJ Max, and etc. but I had a very bad experience with the driver of the hotel shuttle. From the airport, upon arrival at the hotel after the driver hand over to me my luggages he asked for a tip but I told him sorry I do not have have but I can give later time or the following day after I withdraw but he demanded to give that very moment as he said he will be out from work from then on until Monday. So I told him that si am really coz I really don’t have cash and he slammed the door of the shuttle. While I know that “on voluntary basis” guest may give tip to the driver every time I usually give but unfortunately I didn’t have any cash that time. I felt so bad that time so I reported to the Manager. I felt relieved when the Manager told me that this kind of attitude is not being tolerated. I told the Manager that I don’t want the driver to loose his job but this kind of attitude must be corrected. Other than this matter, I don’t have any complain.
Reviewed on Jun. 29, 2025

Studio Allston Hotel
Brighton
Save 100% on your flight
per person
Aug 1 - Aug 8
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.6/10 Excellent! (1,027 reviews)
We have stayed at this hotel a half a dozen times. I like the new food and the beer / wine taps. Didn't like being put in the back building where you have to walk down a long hallway then down 10 stairs w/luggage. Then down another long hallway to get to room. We are 65 yrs old. No warning or asked if we needed help getting to room. I thought being a returning guest and our age would get us a better room as we had all the other times we stayed at this hotel
Reviewed on Jun. 30, 2025

Encore Boston Harbor
Save 100% on your flight
per person
Aug 29 - Sep 1
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (3,026 reviews)
Our family experience was spectacular. Excellent service, perfect and clean rooms. Everything was incredible.
Reviewed on Jul. 2, 2025
Chester Hotel Deals

Even Hotels Manchester Airport by IHG
55 John E. Devine Drive, Manchester, NH
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from Jul 13 to Jul 14
CA $129
CA $140 total
Jul 13 - Jul 14
includes taxes & fees
8.6/10 Excellent! (758 reviews)
"Nice,"
Reviewed on Jun. 30, 2025

DoubleTree by Hilton Manchester Downtown
700 Elm St., Manchester, NH
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Jul 6 to Jul 7
CA $162
CA $176 total
Jul 6 - Jul 7
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
"Nice hotel a short walk from SNHU Arena."
Reviewed on Jun. 26, 2025

Park View Inn - Salem
109 S Broadway, Salem, NH
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from Jul 3 to Jul 4
CA $129
CA $140 total
Jul 3 - Jul 4
includes taxes & fees
8.6/10 Excellent! (1,411 reviews)
"Very nice accommodations, amazing price and cozy little area with tons of convenience!"
Reviewed on Jun. 29, 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.
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