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.
Maverick Suites at 245 Newbury St
Back Bay
Price was CA $1,511, price is now CA $1,069 per person
CA $1,069
per person
Mar 18 - Mar 24
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very Good! (151 reviews)
Room was clean and a good size. Location was perfect - walking distance to where I needed to be.
Reviewed on Dec 2, 2025
Boston Harbor Hotel
North End
Price was CA $2,201, price is now CA $1,490 per person
CA $1,490
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.
Reviewed on Jan 25, 2026
The Charles Hotel
West Cambridge
Price was CA $2,104, price is now CA $1,566 per person
CA $1,566
per person
Mar 12 - Mar 16
found 24 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Room very well appointed and gym was the stand out
Reviewed on Jan 25, 2026
Raffles Boston
Back Bay
Price was CA $3,163, price is now CA $2,384 per person
CA $2,384
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
Everything was great — room was immaculate, hotel was very nice. Would return!
Reviewed on Feb 1, 2026
Chester Hotel Deals
Park View Inn - Salem
109 S Broadway Salem NH
Fully refundableReserve now, pay when you stay
The price is CA $104 per night from Mar 10 to Mar 11
CA $104
CA $113 total
Mar 10 - Mar 11
includes taxes & fees
8.6/10 Excellent! (1,664 reviews)
I was actually impressed with the room when i got there. Very well maintained, clean premises, staff is very well educated and love what they do. The place is in a very convenience location for a super hood price. I will definitely be staying here again and will recomend to my friends.
Reviewed on Feb 2, 2026
La Quinta Inn & Suites by Wyndham Salem NH
8 Keewaydin Dr Salem NH
Fully refundableReserve now, pay when you stay
The price is CA $106 per night from Mar 1 to Mar 2
CA $106
CA $115 total
Mar 1 - Mar 2
includes taxes & fees
8.2/10 Very Good! (1,088 reviews)
Great spot staff was awesome
Reviewed on Feb 2, 2026
DoubleTree by Hilton Manchester Downtown
700 Elm St. Manchester NH
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Feb 9 to Feb 10
CA $167
CA $181 total
Feb 9 - Feb 10
includes taxes & fees
9/10 Wonderful! (1,129 reviews)
clean room friendly staff and warm chocolate chip cookies
Reviewed on Jan 31, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
