Oak Square Holidays from AU$782

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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.

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 AU$942, price is now AU$782 per person
AU$782
per person
3 June - 5 June
found 21 hours ago
Return direct flight included
Sacramento (SAC) to Boston (BOS)
8.6/10 Excellent! (1,001 reviews)
Staff was very friendly and the room was clean and comfortable. It will be even better when they offer breakfast!

Reviewed on 31 Mar 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was AU$2,623, price is now AU$1,751 per person
AU$1,751
per person
3 June - 5 June
found 21 hours ago
Return direct flight included
Sacramento (SAC) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great, however the pool itself was not heated, it was cold and no one really stayed in it for that reason. Thankfully there was a hot tub.

Reviewed on 23 Mar 2026

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was AU$1,538, price is now AU$1,141 per person
AU$1,141
per person
3 June - 5 June
found 21 hours ago
Return direct flight included
Sacramento (SAC) to Boston (BOS)
9.2/10 Wonderful! (2,282 reviews)
Clean rooms; friendly staff and convenient location

Reviewed on 1 Apr 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was AU$1,040, price is now AU$785 per person
AU$785
per person
3 June - 5 June
found 21 hours ago
Return direct flight included
Sacramento (SAC) to Boston (BOS)
8.6/10 Excellent! (1,395 reviews)
Great hotel, in the middle of downtown, walking distance from td garden, friendly staff and great amenities, will be back for sure

Reviewed on 30 Mar 2026

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Price was AU$1,202, price is now AU$980 per person
AU$980
per person
3 June - 5 June
found 21 hours ago
Return direct flight included
Sacramento (SAC) to Boston (BOS)
9/10 Wonderful! (2,995 reviews)
All excellent, room, staff, facilities. Complimentary tea & coffee lounge was a nice touch. I had breakfast in the attached Elephant & Castle pub. 1st morning I had the Eggs Benedict with house potatoes, then 2nd morning I had English brunch both were freshly cooked, excellent waiter service. Totally enjoyable

Reviewed on 31 Mar 2026

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

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

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$319 per night from 5 Apr to 6 Apr
AU$319
5 Apr - 6 Apr
includes taxes & fees
9.2/10 Wonderful! (4,549 reviews)
Very nice

Reviewed on 28 Mar 2026

Omni Boston Hotel at the Seaport
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 AU$264 per night from 5 Apr to 6 Apr
AU$264
5 Apr - 6 Apr
includes taxes & fees
9.6/10 Exceptional! (4,119 reviews)
Exceptionally kind staff

Reviewed on 1 Apr 2026

Seaport Hotel Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is AU$337 per night from 5 Apr to 6 Apr
AU$337
5 Apr - 6 Apr
includes taxes & fees
8.4/10 Very Good! (3,139 reviews)
The heater was so loud, I couldn’t sleep well.

Reviewed on 1 Apr 2026

Hilton Boston Park Plaza
See all 4,030 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 AU$782. 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

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
Harvard University

Harvard University

4.5/5(27 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

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

Activities

Boston Hop-On Hop-Off Trolley Tour

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

AU$75
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
History and Hauntings of Salem Guided Walking Tour

History and Hauntings of Salem Guided Walking Tour

AU$51
per adult
98% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
Boston Harbor Cruise boat with the skyscrapers of the city in the background in Boston

City Cruises Boston: Historic Sightseeing Cruise

AU$66
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
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.