Oak Square Vacations from ￥173,666

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The Latest Oak Square Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Coolidge Corner South Side
Price was ￥208,736, price is now ￥173,666 per person
￥173,666
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (414 reviews)
clean room, friendly staff and location

Reviewed on Oct 21, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was ￥334,890, price is now ￥201,432 per person
￥201,432
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,019 reviews)
This is a lovely hotel with great facilities in a superb location.

Reviewed on Oct 21, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was ￥252,235, price is now ￥188,502 per person
￥188,502
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (475 reviews)
Love to the room, it was perfect for what we needed. Excellent service and excellent location. We will definitely stay here again.

Reviewed on Oct 13, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was ￥243,768, price is now ￥185,758 per person
￥185,758
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (1,021 reviews)
We love the Charles for proximity to the river/races. Rooms are nice and very comfortable. Prices are very steep but head of the Charles weekend is much pricier than usual. Thermostats in room were not responsive. Drafty windows. Chilly overall. Free breakfast?? Never got, never offered even when I cked.

Reviewed on Oct 21, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was ￥262,672, price is now ￥204,499 per person
￥204,499
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (1,008 reviews)
We enjoyed everything about the hotel and its location. I will be booking here again!

Reviewed on Oct 20, 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 which includes night scenes and a city as well as a small group of people

Downtown Boston

4.5/5(2,415 area reviews)

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

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 ￥28,711 per night from Nov 23 to Nov 24
￥28,711
￥34,194 total
Nov 23 - Nov 24
includes taxes & fees
9.6/10 Exceptional! (3,575 reviews)
Accessible and very nice hotel.

Reviewed on Oct 22, 2025

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥16,755 per night from Nov 23 to Nov 24
￥16,755
￥19,512 total
Nov 23 - Nov 24
includes taxes & fees
8.8/10 Excellent! (2,198 reviews)
Very quirky hotel, clean and excellent facilities. The shared bathroom wasn’t an issue as you get a full bathroom to yourself as well as a gown, slippers and towels! The coffee in reception was amazing and the banana cake to die for! Staff were very friendly and we felt very safe walking around the ...

Reviewed on Oct 19, 2025

The Revolution Hotel
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
70 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥22,636 per night from Nov 23 to Nov 24
￥22,636
￥26,361 total
Nov 23 - Nov 24
includes taxes & fees
9.2/10 Wonderful! (3,952 reviews)
Great hotel. Location is perfect! Staff were a little odd, very young, they didn’t have the best hospitality.

Reviewed on Oct 19, 2025

citizenM Boston North Station
See all 3,751 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 vacation package cost?
From just ￥173,666. 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.

Discover the most popular places to visit in Oak Square

Fenway Park which includes a sporting event and night scenes 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 showing a city and heritage architecture

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
Boston Common featuring landscape views, a skyscraper and flowers

Boston Common

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

View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

￥5,162
per adult
86% of travellers recommend
View Boston Observation Deck Admission Tickets
Hear the legendary true stories of Revolutionary Bostonians like Paul Revere, Midnight Rider at the Old North Church

Boston: Freedom Trail History Small Group Walking Tour

￥8,115
per adult
100% of travellers recommend
Boston: Freedom Trail History Small Group Walking Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

￥11,872
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
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.