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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,411, price is now CA $706 per person
CA $706
per person
Jan 29 - Feb 1
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $1,530, price is now CA $963 per person
CA $963
per person
Jan 29 - Jan 31
just found
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,397, price is now CA $1,548 per person
CA $1,548
per person
Jan 29 - Feb 1
just found
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,383, price is now CA $1,635 per person
CA $1,635
per person
Jan 29 - Feb 1
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)
The only place I’ll stay in Boston

Reviewed on Nov 7, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $1,400, price is now CA $1,006 per person
CA $1,006
per person
Dec 16 - Dec 20
found 22 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8.8/10 Excellent! (1,636 reviews)
We would consider staying here again, but for the price there are probably better options nearby. It was conveniently located near the train station and room views were neat!

Reviewed on Nov 7, 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
A nighttime street scene with illuminated trees, a market stall, and historic buildings.

Downtown Boston

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

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
The price is CA $197 per night from Nov 22 to Nov 23
CA $197
CA $287 total
Nov 22 - Nov 23
includes taxes & fees
Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
The price is CA $150 per night from Nov 25 to Nov 26
CA $150
CA $174 total
Nov 25 - Nov 26
includes taxes & fees
9/10 Wonderful! (3,021 reviews)
"One of the cleanest hotels. Great location and easily walkable to the Boston commons"

Reviewed on Nov 7, 2026

The Revolution Hotel
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
The price is CA $171 per night from Nov 23 to Nov 24
CA $171
CA $247 total
Nov 23 - Nov 24
includes taxes & fees
Seaport Hotel Boston
See all 4,000 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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an Oak Square vacation package cost?
From just CA $706. 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.

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $69
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 $119
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

CA $65
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
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.