Shirley Vacation Packages
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Save up to CA $1,096 when you book a flight and hotel together*
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Your Shirley Vacation
When you book a Shirley vacation package, it's all about letting go and enjoying your adventure to the fullest. Delve into the highlights of this lively city knowing that everything has been taken care of before you go. Any trip to Shirley needs a well-planned itinerary. Fill yours with leading attractions like The Mall at Whitney Field, Nashoba Paddler and Harvard Town Beach. Stop dreaming and start adventuring. Explore the wide range of options on Expedia today and put your Shirley vacation plans into gear!
Top Shirley Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Raffles Boston
Back Bay
Price was CA $3,029, price is now CA $1,663 per person
CA $1,663
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
9.6/10 Exceptional! (154 reviews)
Staff went above and beyond everyday! The dining options and location were amazing.
Reviewed on Sep. 2, 2025
The Langham, Boston
Downtown Boston
Price was CA $2,181, price is now CA $1,368 per person
CA $1,368
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,007 reviews)
First rate hotel. Definitely a Luxury hotel stay!
Reviewed on Sep. 1, 2025
Boston Harbor Hotel
North End
Price was CA $2,163, price is now CA $1,411 per person
CA $1,411
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
We had a wonderful stay at the Boston Harbor Hotel - the staff was friendly and our room excellent! Thank you!
Reviewed on Aug. 31, 2025
The Revolution Hotel
South End
Price was CA $1,510, price is now CA $1,001 per person
CA $1,001
per person
Oct 24 - Oct 28
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (2,140 reviews)
It was a great experience. A bit small for four people in one room. But we made due.
Reviewed on Sep. 2, 2025
Shirley Hotel Deals
Bedford Plaza Hotel - Boston
340 Great Road, Bedford, MA
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Sep 7 to Sep 8
CA $145
CA $162 total
Sep 7 - Sep 8
includes taxes & fees
Courtyard by Marriott Boston Marlborough
75 Felton St, Marlborough, MA
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Sep 7 to Sep 8
CA $186
CA $207 total
Sep 7 - Sep 8
includes taxes & fees
AVIA Residences on Research - Extended Stay
25 Connector Road, Westborough, MA
The price is CA $103 per night from Oct 1 to Oct 2
CA $103
CA $115 total
Oct 1 - Oct 2
includes taxes & fees
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.