Oak Square Vacation Packages

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  • Better together

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

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

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Top Holiday Package Deals in Oak Square

Price found within the past 48 hours. Click for updated prices.
enVision Hotel Boston Everett

enVision Hotel Boston Everett

2 out of 5
Price was CA $1,230, price is now CA $857 per person
CA $857
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.6/10 Excellent! (1,007 reviews)
Charles is the best ever!! Always friendly & helpful!!

Reviewed on Apr 27, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $3,159, price is now CA $1,886 per person
CA $1,886
per person
Jun 16 - Jun 19
found 9 hours ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
Private lounge offered three meals, wine, hard liquor, coffee, fruit, ice cream, etc. Well stocked & staff was superb

Reviewed on Apr 26, 2026

Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
Bay Village
Price was CA $1,791, price is now CA $1,186 per person
CA $1,186
per person
Jun 11 - Jun 14
found 7 hours ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
8.4/10 Very Good! (3,127 reviews)
Great location, very clean!

Reviewed on Apr 24, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $4,348, price is now CA $2,884 per person
CA $2,884
per person
Jun 16 - Jun 19
found 9 hours ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (253 reviews)
The photos doesn’t give this place justice.

Reviewed on Mar 24, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $1,844, price is now CA $1,242 per person
CA $1,242
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
8.8/10 Excellent! (1,441 reviews)
Helpful staff. In particular, there was a man named Carlos at the front who helped a lot.

Reviewed on Apr 27, 2026

Where to stay in Oak Square

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

Oak 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 $230 per night from May 3 to May 4
CA $230
CA $315 total
May 3 - May 4
includes taxes & fees
9.6/10 Exceptional! (4,235 reviews)
Very nice room and great service.

Reviewed on Apr 27, 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 $292 per night from May 1 to May 2
CA $292
CA $395 total
May 1 - May 2
includes taxes & fees
9.2/10 Wonderful! (4,606 reviews)
Great hotel

Reviewed on Apr 27, 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 $342 per night from May 26 to May 27
CA $342
CA $454 total
May 26 - May 27
includes taxes & fees
9.4/10 Exceptional! (5,025 reviews)
Lovely hotel, great location. Staff were friendly and helpful.

Reviewed on Apr 27, 2026

The Godfrey Hotel Boston
See all 4,152 properties in Oak 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 an Oak Square vacation package cost?
From just CA $857. Yes, you read that right. Our Oak Square packages are an awesome way to make your budget last longer. Combine your preferred hotels, flights and car rentals and explore this fabulous destination.
How do I get a cheap travel package to Oak Square?
Bundle your hotel and flight bookings, toss in extras such as tours, and save with an Oak Square vacation package. You won't just pick up amazing discounts on your trip — you'll have loads of choice within your reach too. When you book through Expedia, you'll have your pick of over 550 airlines and 1,000,000 properties around the world. Your next affordable adventure starts right here, right now!
Where should I stay in Oak Square?
Urban adventurers come from all corners of the globe to see Fenway Park and TD Garden in Oak Square. Book a room close to these popular attractions to make sightseeing easy.
What are the top hotels in Oak Square?
If it's comfort and convenience you want, you can't go past Luxurious Urban Oasis With Patio And Free Parking. Spend your nights relaxing here and your days wandering around Oak Square's finest sights.
How far in advance should I book my Oak Square vacation?
Travelers are generally able to browse international fares on Expedia up to 12 months prior to departure. Booking late? With a stroke of luck, it's still possible to nab a cheaper ticket only weeks before your journey.
What does an Expedia Oak Square travel package include?
Flights, hotels and rental cars, or any combination of the three — the choice is all yours! Whether you're exploring Oak Square with the family or adventuring solo, there's a bundle to suit every style and budget. Once you've made your booking, why not add on a couple of activities?
What should I know before booking an Oak Square travel package?
You can save a tidy sum by combining your airfares, hotels and rental cars. Once you've created your package, you can add on things like tours and activities. Your next awesome vacation is only a few clicks away.
Can I choose my airline with an Oak Square Expedia vacation package?
Yes, and with over 550 airlines to pick from globally, it's all about choice. Have a look through the available options and find out which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Oak Square vacation package?
It's good to know that you can cancel your Oak Square booking if your travel plans have been upended. Whether you'll incur a fee or not depends on your hotel, airline or car rental company. You may be able to cancel or change your booking for free if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.

Discover the most popular places to visit in Oak 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.