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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,221, price is now CA $760 per person
CA $760
per person
Nov 1 - Nov 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
Price was CA $3,072, price is now CA $1,733 per person
CA $1,733
per person
Oct 10 - Oct 17
found 2 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
8.6/10 Excellent! (1,070 reviews)
The staff was friendly. Room was clean and met our needs. Expedia VIP allowed the resort fee to be waived which was wonderful.

Reviewed on Aug. 18, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $3,694, price is now CA $2,099 per person
CA $2,099
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
The Reffles Hotel is a fabulous place to stay. Hotel is amazing with a wonderful friendly staff.

Reviewed on Aug. 20, 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Price was CA $2,224, price is now CA $1,393 per person
CA $1,393
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (235 reviews)
We enjoyed having the bistro on site.

Reviewed on Jul. 17, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,896, price is now CA $1,215 per person
CA $1,215
per person
Oct 30 - Nov 2
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
The beds are the main thing that keep me coming black, so comfortable, especially after a long day of walking around Boston. I will say we were disappointed that the inside of our coffee machine was very dirty.. something i think shouldn't be missed when cleaning since we love a good morning coffee in the room , but had to settle for going to a coffee shop. We tried ordering room service , but after waiting over 1hr we ended up calling to cancel it. For the amount of money we paid , i think they could step their game up when it comes to service and details.

Reviewed on Aug. 16, 2025

Ready to book your vacation to Chelsea?

 

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Chelsea Hotel Deals

Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea

Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea

2.5 out of 5
200 Maple St, Chelsea, MA
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from Aug 24 to Aug 25
CA $246
CA $275 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (968 reviews)
"Good"

Reviewed on Aug. 17, 2025

Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea
Hampton Inn Boston Logan Airport Chelsea

Hampton Inn Boston Logan Airport Chelsea

2.5 out of 5
200 2nd Street, Chelsea, MA
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from Aug 24 to Aug 25
CA $225
CA $252 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (2,109 reviews)
"Nice place, especially close to airport"

Reviewed on Aug. 17, 2025

Hampton Inn Boston Logan Airport Chelsea
Holiday Inn Boston Logan Airport - Chelsea by IHG

Holiday Inn Boston Logan Airport - Chelsea by IHG

3 out of 5
1012 BROADWAY STREET, Chelsea, MA
Fully refundable
The price is CA $288 per night from Aug 24 to Aug 25
CA $288
CA $322 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Overall very clean hotel, the pond in the back along with a walking path makes a great spot to catch the sunrise. Only thing I wish they offered was shuttle to and from the airport."

Reviewed on Aug. 13, 2025

Holiday Inn Boston Logan Airport - Chelsea by IHG
See all 3,748 properties in Chelsea
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Chelsea

Fenway Park featuring a sporting event and night scenes as well as a large group of people

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University which includes a city and heritage architecture

Harvard University

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common which includes flowers, a garden and landscape views

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.

Boston Common

What to do in Chelsea

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $109
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $97
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

CA $47
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Chelsea

Frequently asked questions

How much does a Chelsea vacation package cost?
Offering great value package deals from CA $760 on Expedia, you'll be pleasantly surprised at how much a vacation to Chelsea costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chelsea?
December, January and February are great times to search for cheap Chelsea vacation packages. Choosing to travel in less busy months means you can usually find reduced prices on hotels and flights.
How many days is enough for Chelsea?
To fully enjoy a Chelsea vacation, we suggest booking for 2 days. Split your time between visiting Boston Common, Copley Square and other top attractions, on top of experiencing neighbourhoods like South Boston and D Street - West Broadway. If you've got some spare time, add a day trip or tour to your Chelsea vacation itinerary.
How to find the best Chelsea package deals?
Use Expedia's handy filters to help you find some fabulous Chelsea package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Chelsea package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Chelsea vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and accommodations individually. Better still, you can personalize your Chelsea getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Chelsea?
If you've got your Chelsea travel dates finalized, book early to score some incredible deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Chelsea?

  1. Choose when to travel: Check your schedule and get packing. Your preferred season and the activities available will also help you decide when to escape to Chelsea.
  2. Work out your budget: Make sure you have enough money to pay for everything from food and transportation to flights and experiences. Your hotel will probably be the biggest expense during your trip to Chelsea.
  3. Set the duration of your trip: Start by compiling a list of the attractions and activities you want to experience in Chelsea. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your accommodations and airfare: After you've settled on your travel dates and duration, book the ideal Chelsea vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.