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.
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
8.8/10 Excellent! (234 reviews)
We enjoyed having the bistro on site.

Reviewed on Jul. 17, 2025

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
per person
Sep 6 - Sep 9
found 24 hours ago
Roundtrip flight included
Toronto (YTZ) to Boston (BOS)
9.4/10 Exceptional! (435 reviews)
Not my favorite Four Seasons. I requested that they remove any alcohol from my room and they didn’t accommodate that simple request. They seemed hurried. B-

Reviewed on Jun. 22, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Wonderful high end hotel in a fantastic area. Loved being able to walk to the north end!

Reviewed on Aug. 3, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (132 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.

Reviewed on Aug. 5, 2025

The Ritz-Carlton, Boston

The Ritz-Carlton, Boston

5 out of 5
Downtown Boston
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9/10 Wonderful! (383 reviews)
This property is Ritz at its best. From the beautiful lobby and well-appointed room, to the impeccable service from staff at every level - all of whom appear to be empowered to make your stay a great one, Ritz Boston does it right. The onsite restaurant was also top notch. As I looked over the menu, I felt a strong sense that if I went for the New England Clam Chowder, I would not be disappointed. THE best bowl of clam chowder I’ve had in my life!!

Reviewed on Jul. 31, 2025

Ready to book your vacation to Chelsea?

 

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Chelsea Hotel Deals

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 $286 per night from Aug 24 to Aug 25
CA $286
CA $320 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (1,024 reviews)
"Clean"

Reviewed on Aug. 5, 2025

Holiday Inn Boston Logan Airport - Chelsea by IHG
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 $268 per night from Aug 26 to Aug 27
CA $268
CA $299 total
Aug 26 - Aug 27
includes taxes & fees
9/10 Wonderful! (2,085 reviews)
"Very quiet to be so close to the airport. Easy access to the airport and a very nice property"

Reviewed on Aug. 3, 2025

Hampton Inn Boston Logan Airport Chelsea
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 $233 per night from Aug 10 to Aug 11
CA $233
CA $260 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (950 reviews)
"Large Property, staff allowed us to checkout earlier as wewere done with our tournament early. Great place to stay. Only thing is please provide more protein based breakfast items. Very carb heavy."

Reviewed on Aug. 1, 2025

Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea
See all 3,732 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 $108
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
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
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

CA $115
per adult
76% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
See all activities in Chelsea

Frequently asked questions

How much does a Chelsea vacation package cost?
Offering great value package deals from CA $987 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.