Oak Square Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Price was €1,403, price is now €1,089 per person
€1,089
per person
28 Oct - 31 Oct
found 2 days ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8/10 Very Good! (585 reviews)
Overall is pretty good and the only thing that we don’t like it is the water volume of shower head just need to be way a lot more .please turn it up .

Reviewed on 28 Aug 2025

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was €1,522, price is now €1,151 per person
€1,151
per person
28 Oct - 31 Oct
found 2 days ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,073 reviews)
Always a great stay!

Reviewed on 26 Aug 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was €1,877, price is now €1,428 per person
€1,428
per person
28 Oct - 31 Oct
found 2 days ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Well appointed property, close to transit, downtown and highways. We had a lovely stay and look forward to returning soon.

Reviewed on 25 Aug 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was €1,673, price is now €1,287 per person
€1,287
per person
28 Oct - 31 Oct
found 2 days ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (1,010 reviews)
Increased room daily charges at the time of checkout significantly

Reviewed on 24 Aug 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was €1,603, price is now €1,235 per person
€1,235
per person
28 Oct - 31 Oct
found 2 days ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (441 reviews)
Beautiful building, friendly staff, great atmosphere

Reviewed on 16 Aug 2025

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 featuring 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

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 €157 per night from 1 Sept to 2 Sept
€157
1 Sept - 2 Sept
includes taxes & fees
9.6/10 Exceptional! (3,284 reviews)
"Nice hotel in great location"

Reviewed on 27 Aug 2025

Seaport Hotel Boston
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 €249 per night from 1 Sept to 2 Sept
€249
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (3,869 reviews)
"Property was well ran and clean. Expensive but everything in Boston is expensive. It’s like Canada except without the exchange. You better like taxes and toll roads or you won’t like Boston."

Reviewed on 25 Aug 2025

Omni Boston Hotel at the Seaport
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 €184 per night from 1 Sept to 2 Sept
€184
1 Sept - 2 Sept
includes taxes & fees
citizenM Boston North Station
See all 3,685 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 €1,089. 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 showing night scenes and a sporting event as well as a large group of people

Fenway Park

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

Fenway Park
Harvard University which includes heritage architecture and a city

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
New England Aquarium

New England Aquarium

From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips.

New England Aquarium

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

€68
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

€47
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

€29
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
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.