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.
Hotel Ivy Boston Common
Bay Village
Price was CA $1,462, price is now CA $960 per person
CA $960
per person
Jul 3 - Jul 6
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
8.4/10 Very Good! (1,430 reviews)
The area is very good for walking and getting the sense of Boston. The rooms are clean and most importantly the staff is excellent.
Reviewed on May 8, 2026
By the Sea Guests Bed & Breakfast & Suites
Price was CA $2,966, price is now CA $1,944 per person
CA $1,944
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!
Reviewed on Sep 20, 2025
Nantucket Inn
Price was CA $2,846, price is now CA $1,925 per person
CA $1,925
per person
Jul 27 - Jul 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9/10 Wonderful! (670 reviews)
Room was clean upon arrival, but there was no "service" daily .... No bed making, no clean towels, no kleenex, etc. We've stayed at Nantucket Inn several time and always like it. We were very disappointed with the daily service this time.
Reviewed on May 8, 2026
The Ritz-Carlton, Boston
Downtown Boston
Price was CA $5,169, price is now CA $3,563 per person
CA $3,563
per person
Jun 16 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (453 reviews)
Top notch. Every member of the staff was a credit to his or her profession.
Reviewed on May 3, 2026
Chester Hotel Deals
La Quinta Inn & Suites by Wyndham Salem NH
8 Keewaydin Dr Salem NH
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from May 31 to Jun 1
CA $129
CA $140 total
May 31 - Jun 1
includes taxes & fees
8.4/10 Very Good! (1,190 reviews)
Room was clean.
Reviewed on May 8, 2026
La Quinta Inn & Suites by Wyndham Boston-Andover
131 River Rd Andover MA
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from May 10 to May 11
CA $159
CA $177 total
May 10 - May 11
includes taxes & fees
8.2/10 Very Good! (2,074 reviews)
No housekeeping if your stay is more than 2 days. Dirty Towels in hallway and trash from rooms left in hallway. Front desk staff was very helpful and informative. Had to go to front desk to request towels and TP. Elevator floor was not cleaned in the five days we stayed there. OK for one night and ...
Reviewed on May 9, 2026
Sonesta ES Suites Andover Boston
4 Tech Drive Andover MA
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from May 21 to May 22
CA $183
CA $205 total
May 21 - May 22
includes taxes & fees
9/10 Wonderful! (1,014 reviews)
Not my cup
Reviewed on May 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.
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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.
