Oak Square Holidays from £1,012

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Your Oak Square Holiday

Experience all the fabulous things this neighbourhood has to offer with a tailor-made Oak Square holiday package. However you see yourself spending your time here, you'll find endless opportunities for adventure, relaxation and fun. Some nearby attractions to check out during your trip to Oak Square include Harvard Square, Harvard University and Boston College. No matter your travel plans or the size of your budget, booking your ideal Oak Square holiday is simple with Expedia.

Price found within the past 48 hours. Click for updated prices.
Global Luxury Suites East Boston

Global Luxury Suites East Boston

4 out of 5
East Boston
Price was £1,494, price is now £1,012 per person
£1,012
per person
25 Sept - 2 Oct
found 1 day ago
Return direct flight included
Manchester (MAN) to Boston (BOS)
7/10 Good! (161 reviews)
There were a few places to eat near the pier the view of the city was amazing and the tall boat was great for food,dancing and drinking however the vibe is younger college kids. I did enjoy the few places we visited to eat. The parking was horrible, We received no directions and it took us an hour to find someone to check in… I was left with two keys and no directions. I managed and once the sun came up an employee at the front desk named Craig was very helpful. The bed was so uncomfortable I would recommend getting a new more comfortable mattress for the amount we paid. All in all we made the best of it and everything else was okay. Lastly no TV directions I had to purchase Netflix on my own. This was not the best stay provided by Expedia. I was disappointed.

Reviewed on 31 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was £2,397, price is now £1,338 per person
£1,338
per person
3 Oct - 7 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
The room was 5 star and it’s in an ideal location in central Boston. View of Boston harbor is amazing, of course. Restaurant on the harbor was good and the service there was great.

Reviewed on 19 Aug 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was £2,852, price is now £1,738 per person
£1,738
per person
8 Oct - 15 Oct
found 1 day ago
Return direct flight included
London (LON) to Boston (BOS)
8.8/10 Excellent! (235 reviews)
We enjoyed having the bistro on site.

Reviewed on 17 Jul 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was £2,221, price is now £1,406 per person
£1,406
per person
3 Oct - 7 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
Awesome hotel. Staff is great. Best hotel in Boston! And I've stayed at alot of em.

Reviewed on 11 Aug 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was £2,771, price is now £1,859 per person
£1,859
per person
11 Oct - 18 Oct
found 1 day ago
Return direct flight included
London (LHR) to Boston (BOS)
9.4/10 Exceptional! (473 reviews)
Awesome place to stay!

Reviewed on 17 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 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

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 £150 per night from 24 Aug to 25 Aug
£150
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (3,666 reviews)
"For a small room it was very well laid out. Loved the decor and the staff were very friendly and helpful. We did not have the breakfast but nice to have that option."

Reviewed on 18 Aug 2025

citizenM Boston North Station
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 £143 per night from 1 Sept to 2 Sept
£143
1 Sept - 2 Sept
includes taxes & fees
9.6/10 Exceptional! (3,248 reviews)
"This was not the least expensive option, but I certainly got what I paid for. People were just so nice. It was easy to get too easy to get around, just perfect."

Reviewed on 17 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 £229 per night from 5 Sept to 6 Sept
£229
5 Sept - 6 Sept
includes taxes & fees
9/10 Wonderful! (3,849 reviews)
It’s okay
"It was cool but the elevator button didn’t work for my floor. There is also a lot of ghetto people enjoying being hood rich for a weekend, be aware."

Reviewed on 18 Aug 2025

Omni Boston Hotel at the Seaport
See all 3,680 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an Oak Square travel package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Oak Square from just £1,012. And the more you bundle, the more cash you save. The getaway of your dreams has never been more affordable.
If I'm not able to travel, can I cancel my Oak Square travel package?
Don't stress if you're rethinking your Oak Square travel package — it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We realise life can throw the occasional spanner in the works, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we're ready to help.
How do I get a cheap travel package to Oak Square?
Crafting your own Oak Square travel package with Expedia is a simple way to save. We have over 550 airlines and 1,000,000 hotel options throughout the world. With such a broad range to choose from, you'll have no issues creating your dream holiday.
Does Expedia offer Book Now, Pay Later Oak Square holidays?
Your bank balance shouldn't get in the way of taking a holiday, so Expedia has come up with a solution to help. Now that we've formed a partnership with online lender Klarna, it's easier than ever to book an incredible getaway without exhausting your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your trip. Check out these flexible payment options:

  • Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's manageable monthly instalment plans. If paying just a small amount each month sounds right for you, choose this option during the checkout process.
  • Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Consider this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to click that "book now" button, go for a low deposit holiday payment plan with Klarna.

Where should I stay in Oak Square?
Holiday makers come from all over to experience Fenway Park and TD Garden in Oak Square. Stay within a stone's throw of these awesome attractions and visit them whenever you please.
What are the top hotels in Oak Square?
Boston Park Plaza and Embassy Suites Boston Logan Airport are among the most sought-after hotels in Oak Square. Why not look up the facilities and amenities at each and then make a decision?
How far in advance should I book my Oak Square holiday?
It can be tricky to know when is the perfect time to book your trip to Oak Square. But generally the earlier you book, the cheaper the prices. In some cases, you can secure your flights and hotels nearly a year prior to your departure date. If you're hoping for a last-minute getaway, no need to stress! There are incredible deals posted on Expedia every single day.
What does an Expedia Oak Square travel package include?
Hotels, flights and a reliable car for all your road trip adventures. Simply pick and choose your favourite bundle and get access to great discounts. Once you've made your booking, add on some tours and experiences and watch your savings stack up. When it comes to creating your Oak Square holiday, you're the boss!
What should I know before booking an Oak Square travel package?
An Expedia travel package can be customized for your budget and is a fantastic way to make your money go further. How much you include is your call. Rental cars, hotels and flights — mix and match whatever combination suits your plans.
Can I choose my airline with an Oak Square Expedia travel package?
Yes, and with over 550 airlines to choose from around the world, you have loads of choice. Search the available options and see which airline best fits your budget and needs.

Popular places to visit

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 which includes a skyscraper, landscape views and a park

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

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

£58
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

£52
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

£25
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. Flight-inclusive packages are ATOL protected.