Commonwealth Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • 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.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,765, price is now CA $1,147 per person
CA $1,147
per person
Jul 1 - Jul 5
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 Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,579, price is now CA $1,584 per person
CA $1,584
per person
Jul 19 - Jul 24
found 20 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (254 reviews)
Splendid bed and breakfast

Reviewed on Apr 29, 2026

Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End

3 out of 5
South End
Price was CA $2,001, price is now CA $1,303 per person
CA $1,303
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (1,003 reviews)
I had a great experience staying at Staypineapple in the South End. The hotel has a really fun, unique vibe while still feeling clean and well put together. The rooms were cozy but thoughtfully designed, and the bed was honestly one of the most comfortable I’ve slept in. The staff was friendly and welcoming, and the location made it easy to get around Boston and explore nearby restaurants and shops. Small touches like the complimentary coffee and overall atmosphere made the stay feel a little more special. Would definitely stay here again and recommend it to anyone looking for something a bit different from a typical hotel.

Reviewed on Apr 30, 2026

Chatham Tides

Chatham Tides

2.5 out of 5
Price was CA $2,902, price is now CA $1,982 per person
CA $1,982
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (685 reviews)
Excellent Such a great surprise Amazing view. Great staff, very helpful with restaurant recommendations We loved it

Reviewed on Apr 23, 2026

Lighthouse Inn

Lighthouse Inn

3 out of 5
Price was CA $2,047, price is now CA $1,433 per person
CA $1,433
per person
Jun 22 - Jun 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.8/10 Excellent! (182 reviews)
This is a beautiful property located on the beach. It really does not het much better than this. The room was nice and spacious and the views were nothing short of exceptional. The staff was wonderful and a shout out to the GM, John, for being very helpful! And of course the sunsets on West Dennis beach are worth the stay!

Reviewed on Oct 6, 2025

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 $230 per night from May 3 to May 4
CA $230
CA $314 total
May 3 - May 4
includes taxes & fees
9.6/10 Exceptional! (4,248 reviews)
Staff was very nice, property was very well maintained. It was difficult to find the self-parking lot and my coffee maker overflowed the mug in the room even when putting in the minimum required water. Weekend breakfast buffet was not worth the cost. Great place to stay but eat elsewhere.

Reviewed on May 1, 2026

Seaport Hotel Boston
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 $325 per night from May 10 to May 11
CA $325
CA $433 total
May 10 - May 11
includes taxes & fees
9.2/10 Wonderful! (4,608 reviews)
Smallest room I’ve ever seen, the bathroom is less than private.

Reviewed on Apr 30, 2026

Omni Boston Hotel at the Seaport
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
505 Washington Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $241 per night from May 10 to May 11
CA $241
CA $336 total
May 10 - May 11
includes taxes & fees
9.4/10 Exceptional! (5,030 reviews)
We didn’t eat breakfast at the property and did not have a vehicle.

Reviewed on Apr 29, 2026

The Godfrey Hotel Boston
See all 4,227 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 $1,147. 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 $116
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.