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.
By the Sea Guests Bed & Breakfast & Suites
Price was CA $1,434, price is now CA $963 per person
CA $963
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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
Hotel Ivy Boston Common
Bay Village
Price was CA $3,050, price is now CA $1,926 per person
CA $1,926
per person
Jun 18 - Jun 21
found 21 hours ago
Roundtrip flight included
Edmonton (YEG) 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
The Langham, Boston
Downtown Boston
Price was CA $2,923, price is now CA $1,964 per person
CA $1,964
per person
Jun 18 - Jun 21
found 21 hours ago
Roundtrip flight included
Edmonton (YEG) to Boston (BOS)
9.6/10 Exceptional! (1,007 reviews)
Service both at the hotel and restaurants was the one of the best experiences I’ve had
Reviewed on May 2, 2026
Sea Crest Beach Resort
Price was CA $3,369, price is now CA $2,373 per person
CA $2,373
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (268 reviews)
Fantastic ocean front location. Room was oceanfront with great view. Dusty room, floors kind of dirty. Property needs maintenance and upgrading.
Reviewed on May 9, 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! (1,191 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 25 to May 26
CA $159
CA $177 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,075 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 $182 per night from May 17 to May 18
CA $182
CA $203 total
May 17 - May 18
includes taxes & fees
9/10 Wonderful! (1,016 reviews)
Return the incidental fee.
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.
