A cityscape with a prominent downtown area, a river, and a distant skyline.

Oak Square Holidays from £756

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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.

The Latest Oak Square Holiday Packages

Price found within the past 48 hours. Click for updated prices.
  • 11 Jan - 15 Jan

    Boston Lodge and Suites + Flight

    Dorchester
    4 nights
    4.0 star property
    8.4/10 - Very good (194 reviews)
    "The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The..."
    Reviewed October 17, 2026
    Return • Manchester (MAN) - Boston (BOS)
    MAN - BOS • 1 stop BOS - MAN • 1 stop
    £1,380
    £756
    per traveller
    found 1 day ago
    Boston Lodge and Suites
  • 11 Jan - 15 Jan

    Boston Harbor Hotel + Flight

    North End
    4 nights
    5.0 star property
    9.8/10 - Exceptional (1,006 reviews)
    Return • Manchester (MAN) - Boston (BOS)
    MAN - BOS • 1 stop BOS - MAN • 1 stop
    Save 100% on your flight
    £1,903
    £1,181
    per traveller
    found 1 day ago
    Boston Harbor Hotel
  • 27 Dec - 2 Jan

    Raffles Boston + Flight

    Back Bay
    6 nights
    5.0 star property
    9.6/10 - Exceptional (353 reviews)
    "The only place I’ll stay in Boston"
    Reviewed November 7, 2026
    Return • Edinburgh (EDI) - Boston (BOS)
    EDI - BOS • 1 stop BOS - EDI • 1 stop
    £3,046
    £2,086
    per traveller
    found 7 hours ago
    Raffles Boston
  • 11 Jan - 15 Jan

    Four Seasons Hotel Boston + Flight

    Bay Village
    4 nights
    5.0 star property
    9.4/10 - Exceptional (496 reviews)
    Return • Manchester (MAN) - Boston (BOS)
    MAN - BOS • 1 stop BOS - MAN • 1 stop
    £1,952
    £1,453
    per traveller
    found 1 day ago
    Four Seasons Hotel Boston
  • 11 Jan - 15 Jan

    The Newbury Boston + Flight

    Back Bay
    4 nights
    5.0 star property
    9.4/10 - Exceptional (747 reviews)
    "Beautiful hotel and the staff was wonderful. They gave us a corner room with a great view of the city. The room was spacious with a comfortable seating area."
    Reviewed November 7, 2026
    Return • Manchester (MAN) - Boston (BOS)
    MAN - BOS • 1 stop BOS - MAN • 1 stop
    £1,670
    £1,250
    per traveller
    found 1 day ago
    The Newbury Boston

Where to stay in Oak Square

Find the best Oak Square areas for the activities you enjoy most.

Downtown Boston

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.

Back Bay

Parisian boulevards and elegant brownstones conjure a truly romantic atmosphere, perfect for strolling and window shopping.

Seaport District

Join excited crowds enjoying harbor-side views, Revolutionary War-era landmarks, as well as superb restaurants and museums along this thriving waterfront.

Beacon Hill

Lose yourself in the charming streetscapes, historic buildings and village-like atmosphere of Boston’s oldest and wealthiest suburbs.

North End

The ample dining options and captivating waterfront views are just a few popular features of the neighbourhood. Make a stop by Old North Church or Paul Revere House while you're visiting, and jump aboard the metro at Aquarium to get around town.

What to do near Oak Square

Oak Square Hotel Deals

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 travel package cost?

Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Oak Square from just £756. 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.