Oak Square Holidays

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Your Oak Square Holiday

Oak Square is beckoning! Whatever type of break you have in mind, get ready to discover the best of this neighbourhood with an Oak Square holiday package. Your trip to Oak Square wouldn't be complete without exploring top attractions nearby such as Harvard Square, Harvard University and Boston College. Stop dreaming and start doing. When you're ready to book your ideal holiday to Oak Square, Expedia is here to help.

Our guide on 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 showing a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(17 area reviews)

This is Boston’s business district, now and back when the city was just starting.

Find hotels in Downtown Boston

Our pick of the best Oak Square Hotel Deals

Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is AU$186 per night from 4 Jan to 5 Jan
AU$186
4 Jan - 5 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (6,107 reviews)
Yes

Reviewed on 29 Dec 2025

Harborside Inn Of Boston
Hilton Boston Back Bay

Hilton Boston Back Bay

4 out of 5
40 Dalton St Boston MA
Fully refundableReserve now, pay when you stay
The price is AU$291 per night from 4 Jan to 5 Jan
AU$291
4 Jan - 5 Jan 2026
includes taxes & fees
8.4/10 Very Good! (1,250 reviews)
Staff were great.

Reviewed on 28 Dec 2025

Hilton Boston Back Bay
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 AU$303 per night from 5 Jan to 6 Jan
AU$303
5 Jan - 6 Jan 2026
includes taxes & fees
9/10 Wonderful! (4,339 reviews)
Perfect

Reviewed on 27 Dec 2025

Omni Boston Hotel at the Seaport
See all 3,895 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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.

Discover the most popular places to visit in Oak Square

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

Fenway Park

4.5/5(9 reviews)

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

Fenway Park
Boston Common which includes landscape views, a skyscraper and a park

Boston Common

4.5/5(32 reviews)

The oldest public park in the United States, Boston Common is the ideal place to relax, unwind and soak up some history.

Boston Common
TD Garden

TD Garden

4.5/5(6 reviews)

Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area.

TD Garden

Activities

Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

AU$127
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
LEGO Discovery Center Boston Admission Ticket

LEGO Discovery Center Boston Admission Ticket

AU$42
per adult
LEGO Discovery Center Boston Admission Ticket
Built-in 15-minute break at Quincy Market.

The Full Revolutionary Story Epic Small Group Boston Walking Tour

AU$75
per adult
100% of travellers recommend
The Full Revolutionary Story Epic Small Group Boston Walking Tour
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.