Davis Square Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Davis Square

Price found within the past 48 hours. Click for updated prices.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,024, price is now CA $1,255 per person
CA $1,255
per person
Jun 23 - Jun 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (254 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $3,051, price is now CA $1,650 per person
CA $1,650
per person
Jun 27 - Jun 30
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,000 reviews)
The staff were so kind and let us check in early. They constantly asked how we were enjoying the stay and if there was anything that we needed. The property was clean and super cute!

Reviewed on Apr 13, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $2,503, price is now CA $1,593 per person
CA $1,593
per person
Jun 27 - Jun 30
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,435 reviews)
Clean room and good staff. Room is a bit outdated

Reviewed on Apr 15, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $4,737, price is now CA $3,106 per person
CA $3,106
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Boston (BOS)
9.6/10 Exceptional! (253 reviews)
The photos doesn’t give this place justice.

Reviewed on Mar 24, 2026

The Ritz-Carlton, Boston

The Ritz-Carlton, Boston

5 out of 5
Downtown Boston
Price was CA $4,894, price is now CA $3,218 per person
CA $3,218
per person
Jun 27 - Jun 30
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (449 reviews)
Club level is well worth it. The service was wonderful

Reviewed on Apr 16, 2026

Where to stay in Davis Square

Find the best Davis Square areas and neighborhoods for the activities you enjoy most. Learn more about Davis Square
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

Davis Square 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 $232 per night from May 10 to May 11
CA $232
CA $316 total
May 10 - May 11
includes taxes & fees
9.6/10 Exceptional! (4,197 reviews)
A

Reviewed on Apr 18, 2026

Seaport Hotel Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $240 per night from May 10 to May 11
CA $240
CA $336 total
May 10 - May 11
includes taxes & fees
8.4/10 Very Good! (3,122 reviews)
It was a beautiful room. Every staff member was really nice and helpful. Perfect spot if you want to explore the back bay. Close to a lot of things

Reviewed on Apr 18, 2026

Hilton Boston Park Plaza
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 $255 per night from May 10 to May 11
CA $255
CA $353 total
May 10 - May 11
includes taxes & fees
9.2/10 Wonderful! (4,577 reviews)
Everything was perfert. Very friendly staff, nice and clean hotel. Would definitely recommend and stay again.

Reviewed on Apr 18, 2026

Omni Boston Hotel at the Seaport
See all 4,156 properties in Davis Square
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.
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Frequently asked questions

How much does a Davis Square vacation package cost?
Starting from as low as CA $1,255, a vacation package is your portal to cheaper travel. Put together your Davis Square getaway by picking from our extensive range of hotels, flights and rental cars.
How do I get a cheap travel package to Davis Square?
Bundle your flights and hotels, add on extras such as activities or a rental car, and save with a Davis Square vacation package. You won't just land wonderful discounts on your trip — you'll have loads of choice too. When you book through Expedia, you can choose from more than 550 airlines and 1,000,000 properties worldwide. Your affordable vacation starts right here, right now!
Where should I stay in Davis Square?
A vacation in Davis Square wouldn't be complete without paying a visit to Assembly Row, LEGOLAND® Discovery Center and Somerville Theatre. Stay close to these top sights and make sightseeing a breeze.
How far in advance should I book my Davis Square vacation?
It's hard to pick the best time for airfares, but we usually say the earlier, the better. Most international journeys on Expedia become available to compare up to 12 months in advance. If you're booking last minute, don't fret. Low prices occasionally appear just weeks before departure dates.
What does an Expedia Davis Square travel package include?
Expedia has all you need to lock in Davis Square trip, but how your package is structured is your choice. Pick from a combination of hotels, rental cars and flights. In search of some activities or tours to keep you on the go? Once you've made your booking, you can add them on too. No matter your budget or style, there's a vacation package to suit your needs.
What should I know before booking a Davis Square travel package?
You'll save big with an Expedia travel package. Combine your airfares, rental cars and hotels and score fabulous discounts. You're not restricted to hotels, however. Book with us and take your pick of beach villas, city apartments and even glamping tents!
Can I choose my airline with a Davis Square Expedia vacation package?
Yes — that's one of the best things about an Expedia vacation package. You get to choose. We have more than 550 airline partners worldwide, so you have loads of choice when organizing your Davis Square trip.
If I'm not able to travel, can I cancel my Davis Square vacation package?
It's impossible to predict what tomorrow might bring, so it's comforting to know that you can cancel or change your Davis Square vacation package. If your booking was made in the last 24 hours, you may be entitled to a refund. If it's an older booking, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

Discover the most popular places to visit in Davis Square

Fenway Park

Fenway Park

4.5/5(310 reviews)

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

Fenway Park
Harvard University

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.

Harvard University
Gillette Stadium

Gillette Stadium

4.5/5(28 reviews)

Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's great live music and acclaimed theater scene.

Gillette Stadium

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $72
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.