Davis Square Vacation Packages

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    Save up to CA $750 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.
Sunbird ANNEX Resort

Sunbird ANNEX Resort

2 out of 5
Price was CA $1,518, price is now CA $1,030 per person
CA $1,030
per person
Jul 5 - Jul 11
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
7.8/10 Good! (825 reviews)
Everything was good. The room was very plain, but it had everything we needed which was bed, TV, fridge, iron, WiFi. The staff was very gracious.

Reviewed on Oct 19, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $4,122, price is now CA $2,575 per person
CA $2,575
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Very nice hotel. Clean, great staff!

Reviewed on Apr 22, 2026

Lighthouse Inn

Lighthouse Inn

3 out of 5
Price was CA $2,721, price is now CA $1,775 per person
CA $1,775
per person
Jul 5 - Jul 11
found 2 days ago
Roundtrip flight included
Toronto (YTO) 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

Chatham Tides

Chatham Tides

2.5 out of 5
Price was CA $3,418, price is now CA $2,240 per person
CA $2,240
per person
Jul 5 - Jul 11
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (682 reviews)
Excellent Such a great surprise Amazing view. Great staff, very helpful with restaurant recommendations We loved it

Reviewed on Apr 23, 2026

The Mansion at Ocean Edge

The Mansion at Ocean Edge

4 out of 5
Price was CA $4,410, price is now CA $3,018 per person
CA $3,018
per person
Jul 5 - Jul 11
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very Good! (1,001 reviews)
Unfortunately, we went during the slow season. They don't open fully until May 1st. The bar wasn't open until 5pm and restaurants were not open. Pool was closed. No chairs on the deck. Everything was covered. Property was nice. Just would have been nice to have a few options.

Reviewed on Apr 24, 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 $231 per night from May 3 to May 4
CA $231
CA $316 total
May 3 - May 4
includes taxes & fees
9.6/10 Exceptional! (4,225 reviews)
Convenient location, very helpful valet staff.

Reviewed on Apr 26, 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 $239 per night from May 10 to May 11
CA $239
CA $335 total
May 10 - May 11
includes taxes & fees
9.2/10 Wonderful! (4,602 reviews)
the pool was great!

Reviewed on Apr 26, 2026

Omni Boston Hotel at the Seaport
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 $173 per night from Apr 30 to May 1
CA $173
CA $202 total
Apr 30 - May 1
includes taxes & fees
9/10 Wonderful! (2,573 reviews)
Beautiful entrance, comfy beds, quiet rooms, restrooms clean and easy to get in and out. Highly recommend

Reviewed on Apr 25, 2026

The Revolution Hotel
See all 4,167 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.
All Inclusive Vacations
All Inclusive Vacations
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Frequently asked questions

How much does a Davis Square vacation package cost?
Starting from as low as CA $1,030, 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

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

Fenway Park
Harvard University

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
Gillette Stadium

Gillette Stadium

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 $79
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
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
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
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.