Commonwealth Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Melody Jeng

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Commonwealth

Price found within the past 48 hours. Click for updated prices.
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Price was CA $1,571, price is now CA $1,114 per person
CA $1,114
per person
Jun 16 - Jun 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very Good! (1,441 reviews)
Friendly staff clean room good location

Reviewed on May 14, 2026

Meco Hotel - Hostel

Meco Hotel - Hostel

2 out of 5
West End
Price was CA $3,098, price is now CA $1,579 per person
CA $1,579
per person
Jul 23 - Jul 28
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to Boston (BOS)
8.6/10 Excellent! (406 reviews)
1st time, felt safe. Towels were available. Bring your own lock. 1 block from train station. And good food and stores nearby

Reviewed on May 15, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,546, price is now CA $1,626 per person
CA $1,626
per person
Jul 21 - Jul 26
found 16 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Boston (BOS)
9.6/10 Exceptional! (255 reviews)
Splendid bed and breakfast

Reviewed on Apr 29, 2026

Nantucket Inn

Nantucket Inn

3.5 out of 5
Price was CA $3,606, price is now CA $2,485 per person
CA $2,485
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (676 reviews)
Clean, friendly staff, nice indoor pool, good breakfast sanwich

Reviewed on May 12, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $3,165, price is now CA $2,231 per person
CA $2,231
per person
Jul 23 - Jul 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,007 reviews)
Right in heart of town

Reviewed on May 12, 2026

Where to stay in Commonwealth

Find the best Commonwealth areas and neighborhoods for the activities you enjoy most. Learn more about Commonwealth
Downtown Boston

Downtown Boston

4.5/5(197 area reviews)

Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.

Find hotels in Downtown Boston

Commonwealth Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $318 per night from May 25 to May 26
CA $318
CA $417 total
May 25 - May 26
includes taxes & fees
9.6/10 Exceptional! (4,345 reviews)
Everyone was so welcoming, so accommodating, so conveniently located—the highest recommendation.

Reviewed on May 15, 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from May 25 to May 26
CA $174
CA $202 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (2,604 reviews)
This was such a fun location and a great way for people to share a room and save some money in downtown Boston. We loved the experience, the hotel, and the staff. 10/10. Would stay here again!

Reviewed on May 11, 2026

The Revolution Hotel
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from May 29 to May 30
CA $246
CA $342 total
May 29 - May 30
includes taxes & fees
9.2/10 Wonderful! (4,644 reviews)
This is one of the best decisions I ever made honestly!! They were all so sweet. The hotel was gorgeous and I had written a note for them before coming that it was my birthday and if I could get the highest floor. They had 22 floors and gave me the 20th and not just that but they also had a cup desert ...

Reviewed on May 13, 2026

Omni Boston Hotel at the Seaport
See all 4,207 properties in Commonwealth
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

Frequently asked questions

How much does a Commonwealth vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Commonwealth from just CA $1,114. And the more you bundle, the more cash you save. Your dream escape has never been more affordable.
How do I get a cheap travel package to Commonwealth?
You'll save tons of cash if you combine your hotels, car rentals and flights into a Commonwealth vacation package. Sometimes cheap means fewer options. But not with Expedia. We offer more than 550 air carriers and 1,000,000 hotels globally, which means you'll always have plenty of options to choose from. Want to save even more? Add some interesting activities to your package deal to unlock even more discounts! After all, travel is about more than just getting to your destination.
Where should I stay in Commonwealth?
Make sightseeing easy by staying someplace just a stone's throw away from Commonwealth's big attractions. Fenway Park and TD Garden are two of the most popular.
What are the top hotels in Commonwealth?
Reserve a room at AC Hotel by Marriott Boston Cleveland Circle. It's one of the neighborhood's most sought-after properties. Another well-known option in Commonwealth is Remodeled Spacious Apartment In Perfect Location.
How far in advance should I book my Commonwealth vacation?
Savvy travelers often book as early as possible. You can usually look up international fares on Expedia up to 12 months before your flight. If you're purchasing tickets last minute, don't despair. Budget prices sometimes occur in the last weeks before departure.
What does an Expedia Commonwealth travel package include?
Packages include hotels, flights and rental cars, but you can mix and match them to create your dream Commonwealth escape. You can also add on a few activities and tours once you've made your booking. You're the boss! When you combine your bookings with Expedia, you'll get discounts you won't find elsewhere.
What should I know before booking a Commonwealth travel package?
Our prices are always low. However, you'll score even better deals if you book your flights, hotels and car rentals together. With an Expedia package, you'll always get transparent pricing and a great range of choice.
Can I choose my airline with a Commonwealth Expedia vacation package?
Yes, and with more than 550 airlines to pick from throughout the world, you have loads of choice. Browse the available options and see which airline suits your needs and budget.
If I'm not able to travel, can I cancel my Commonwealth vacation package?
Don't worry if you're rethinking your Commonwealth vacation package — it's possible to change or amend your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We totally get that your circumstances can suddenly change, so look up our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.

Things to do

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

CA $79
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $115
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $47
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Boston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.