Oak Square Packages (Flight + Hotel)

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    Save up to ฿4,531 when you book a flight and hotel together*
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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 which includes a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(94 area reviews)

The heart of America’s revolutionary history lies in the center of this city. Uncover the story of the nation and enjoy excellent arts and dining venues.

Find hotels in Downtown Boston

Top hotels in Oak Square

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ฿5,995 per night from 24 Aug to 25 Aug
฿5,995
฿8,316 total
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (3,753 reviews)
"The hotel was clean and very pretty. The pool was very nice."

Reviewed on 31 Jul 2025

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ฿6,185 per night from 10 Aug to 11 Aug
฿6,185
฿7,203 total
10 Aug - 11 Aug
includes taxes & fees
9.2/10 Wonderful! (1,504 reviews)
"Nice new property. Small clean modern rooms. Best for one person traveling for a short period of time. The umbrella has a check in and out. I checked it in but the employee never noted it even after asking for my room number. If I didn’t catch it I would have been charged for a $20 umbrella that ..."

Reviewed on 28 Jul 2025

citizenM Boston Back Bay
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ฿5,694 per night from 24 Aug to 25 Aug
฿5,694
฿6,631 total
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (3,591 reviews)
"Not being able to walk around the bed to get in the opposite side is difficult but it wasn't a big issue. Having to control everything off of an ipad is novel but I imagine if it was accidentally dropped and damaged it would be a pretty expensive bill. A very delicate and expensive remote control ..."

Reviewed on 31 Jul 2025

citizenM Boston North Station
See all 3,696 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.

Frequently asked questions

How much does an Oak Square holiday package cost?
From just . 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 holiday 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 holiday?
Travellers 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 holiday is only a few clicks away.
Can I choose my airline with an Oak Square Expedia holiday 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 holiday 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.

Popular places to visit

Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(61 reviews)

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

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(102 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
Boston Common which includes a skyscraper, landscape views and a park

Boston Common

4.5/5(204 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

Things to do

Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

฿1,766
per adult
86% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

฿1,103
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
BEST New York City Day Tour from Boston

New York City Day Tour from Boston

฿5,677
per traveller
100% of travellers recommend
New York City Day Tour from Boston
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.