Oak Square Holidays from £1,102
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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.
Boston Harbor Hotel
North End
£1,102
per person
24 Nov - 29 Nov
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
Great hotel at a terrific site. The North End restaurants and Faneuil Hall are both at walkable distances. Everywhere we were in the Hotel there was always a staff member asking if we needed help. We loved out stay at the Boston Harbor Hotel.
Reviewed on 22 Sept 2026
Raffles Boston
Back Bay
£1,206
per person
24 Nov - 29 Nov
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (312 reviews)
The room is beautiful, minimalist, luxurious, and extremely comfortable. In my opinion, it’s perfect for a solo traveler or, especially, for a couple. Since the room is on the smaller side, I personally wouldn’t consider it ideal for families traveling with children.
For a romantic getaway, however, it was absolutely perfect. One of the highlights is having an incredible and highly sought-after restaurant right inside the building. The dining experience was exceptional — the food was impeccable, the atmosphere was beautiful, and it truly added another level to our stay. I highly recommend making the restaurant part of the experience.
To make our stay even more special, I hired a local company, Our Love Box (@ourlovebox on Instagram), to create a romantic surprise in the room. I ordered a gorgeous bouquet of 100 roses along with a full romantic room setup, and the result was absolutely stunning.
What impressed me even more was how seamless everything was. They handled the entire setup and came back the following day to remove all of the decorations. Once they were finished, you couldn’t even tell there had been a setup in the room — everything was left exactly as it was before.
Overall, the entire experience was incredible. Between the luxurious and comfortable room, the exceptional dining experience, and the romantic setup, it was truly memorable. I highly recommend this experience for couples celebrating an anniversary, birthday, proposal, or simply looking for a special
Reviewed on 21 Sept 2026
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
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
1 out of top 10 points of interest in this area
Parisian boulevards and elegant brownstones conjure a truly romantic atmosphere, perfect for strolling and window shopping.
Seaport District
1 out of top 10 points of interest in this area
Join excited crowds enjoying harbor-side views, Revolutionary War-era landmarks, as well as superb restaurants and museums along this thriving waterfront.
Beacon Hill
1 out of top 10 points of interest in this area
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 Boston Harbor or Old North Church while you're visiting, and jump aboard the metro at Aquarium to get around town.
Top hotels in Oak Square
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
£344
2 Oct - 3 Oct
includes taxes & fees
9.2/10 Wonderful! (4,830 reviews)
"Great clean"
Reviewed on 23 Sept 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
£208
27 Sept - 28 Sept
includes taxes & fees
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
£253
4 Oct - 5 Oct
includes taxes & fees
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 £1,102. 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.
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
£36
per adult
90% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
£52
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
£34
per adult
80% of travellers recommend
* 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.