Chelsea Vacation Packages
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Your Chelsea Vacation
Lock in a Chelsea vacation package and prepare to experience everything this city has to offer. Consider basing yourself in the neighborhood of Downtown Boston, which is great for nightlife, shopping and bars and pubs. A trip to Chelsea is an excellent opportunity to see the sights. Be sure to visit big-name attractions such as Fenway Park, Boston Common and Boston Museum of Fine Arts. A couple of quick clicks is all it takes to put together a tailor-made Chelsea vacation on Expedia.
Top Chelsea Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Cambria Hotel & Suites Plymouth
Price was CA $881, price is now CA $589 per person
CA $589
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (30 reviews)
Very impressed! Very clean, friendly staff, felt safe, the room was far bigger than expected, I’ll be back!
Reviewed on Sep. 1, 2025
Raffles Boston
Back Bay
Price was CA $2,572, price is now CA $1,444 per person
CA $1,444
per person
Nov 5 - Nov 8
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) 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
Boston Harbor Hotel
North End
Price was CA $4,229, price is now CA $2,596 per person
CA $2,596
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Great harbor views! Room service was superb as well. Everyday we came back to an organized room and sometimes sweets, creams. The reception desk was also good in answering any questions. Excellent location. Would stay again.
Reviewed on Sep. 3, 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 1 day 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
Hotel AKA Back Bay
Back Bay
Price was CA $2,184, price is now CA $1,457 per person
CA $1,457
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (1,116 reviews)
The room was clean and well-appointed, the staff courteous and kind. The only thing was that it took 25 min to get our car in the morning from the valet, which I understand with city parking; I would just have requested it earlier. I’d definitely stay here again!
Reviewed on Sep. 3, 2025
Chelsea Hotel Deals
Hampton Inn Boston Logan Airport Chelsea
200 2nd Street, Chelsea, MA
Fully refundableReserve now, pay when you stay
The price is CA $270 per night from Sep 7 to Sep 8
CA $270
CA $302 total
Sep 7 - Sep 8
includes taxes & fees
Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea
200 Maple St, Chelsea, MA
Fully refundableReserve now, pay when you stay
The price is CA $263 per night from Sep 7 to Sep 8
CA $263
CA $293 total
Sep 7 - Sep 8
includes taxes & fees
Holiday Inn Boston Logan Airport - Chelsea by IHG
1012 BROADWAY STREET, Chelsea, MA
Fully refundable
The price is CA $339 per night from Sep 8 to Sep 9
CA $339
CA $379 total
Sep 8 - Sep 9
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.
Discover the most popular places to visit in Chelsea
Fenway Park
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
Harvard University
Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.
Boston Common
The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.
What to do in Chelsea
Boston CityPASS®: Admission to Top 4 Attractions
CA $109
per adult
90% of travellers recommend
View Boston Observation Deck Admission Tickets
CA $47
per adult
84% of travellers recommend
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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.