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.
By the Sea Guests Bed & Breakfast & Suites
Price was CA $1,171, price is now CA $829 per person
CA $829
per person
Jul 23 - Jul 26
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
The Langham, Boston
Downtown Boston
Price was CA $2,259, price is now CA $1,445 per person
CA $1,445
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
Service both at the hotel and restaurants was the one of the best experiences I’ve had
Reviewed on May 2, 2026
Hotel Ivy Boston Common
Bay Village
Price was CA $1,470, price is now CA $982 per person
CA $982
per person
Jul 29 - Aug 1
found 19 hours ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
8.4/10 Very Good! (1,441 reviews)
I was only here because I had an early flight out of Boston the next morning. I arrived way past standard check in time (3-4 pm), and the staff were very communicative, friendly and understanding. The room did the trick for just an overnight. Comfortable beds with comfortable pillows. Loved the bathroom. Loved the lighting. Only thing to note for future travelers that may be “negative”: The pictures make the room look much bigger than it is, like the size of a standard hotel room. It is about 1/4 of the size of a normal hotel room. At least this was the case for my room.
Reviewed on May 6, 2026
Eurostars The Boxer
West End
Price was CA $1,912, price is now CA $1,339 per person
CA $1,339
per person
Jul 29 - Aug 1
found 19 hours ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
8.8/10 Excellent! (1,451 reviews)
First time in Boston and it was perfect. Would book again.
Reviewed on May 2, 2026
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 $219 per night from May 24 to May 25
CA $219
CA $245 total
May 24 - May 25
includes taxes & fees
9/10 Wonderful! (2,915 reviews)
Then room was large comfortable and clean. The staff were helpful and respectful. The breakfast was good. I do think the hotel is a bit further than from the airport than advertised. My flight was late and I missed the last shuttle and the cab ride was almost $30. It all worked out fime.
Reviewed on May 6, 2026
Doubletree By Hilton Boston Logan Airport Chelsea
201 Everett Ave Chelsea MA
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from May 24 to May 25
CA $225
CA $252 total
May 24 - May 25
includes taxes & fees
8.6/10 Excellent! (1,773 reviews)
Todo bien
Reviewed on May 6, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $234 per night from May 10 to May 11
CA $234
CA $319 total
May 10 - May 11
includes taxes & fees
9.6/10 Exceptional! (4,289 reviews)
Beautiful hotel
Reviewed on May 6, 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.
Discover the most popular places to visit in Chelsea
Fenway Park
4.5/5(310 reviews)
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
Harvard University
4.5/5(284 reviews)
Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.
Boston Common
4.5/5(522 reviews)
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 Old Town Trolley Hop-on Hop-Off City Tour
CA $79
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $116
per adult
92% of travellers recommend
View Boston Observation Deck Admission Tickets
CA $47
per adult
88% 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.
