Oak Square Holidays from £1,197

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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.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was £1,774, price is now £1,197 per person
£1,197
per person
8 Jul - 12 Jul
found 1 day ago
Return flight included
London (LON) to Boston (BOS)
9.6/10 Exceptional! (254 reviews)
Splendid bed and breakfast

Reviewed on 29 Apr 2026

Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Save 100% on your flight
Price was £2,563, price is now £1,571 per person
£1,571
per person
11 Jun - 16 Jun
found 24 hours ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
8.4/10 Very Good! (1,441 reviews)
I was only here because I had an early flight out of Boston the next morning. I arrived way past standard check in time (3-4 pm), and the staff were very communicative, friendly and understanding. The room did the trick for just an overnight. Comfortable beds with comfortable pillows. Loved the bathroom. Loved the lighting. Only thing to note for future travelers that may be “negative”: The pictures make the room look much bigger than it is, like the size of a standard hotel room. It is about 1/4 of the size of a normal hotel room. At least this was the case for my room.

Reviewed on 6 May 2026

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was £3,604, price is now £2,500 per person
£2,500
per person
22 Jun - 29 Jun
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9.4/10 Exceptional! (631 reviews)
very nice hotel and location! We loved it!

Reviewed on 1 May 2026

The Ritz-Carlton, Boston

The Ritz-Carlton, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was £3,321, price is now £2,375 per person
£2,375
per person
17 Jun - 22 Jun
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9/10 Wonderful! (453 reviews)
Top notch. Every member of the staff was a credit to his or her profession.

Reviewed on 3 May 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was £2,626, price is now £1,898 per person
£1,898
per person
8 Jul - 12 Jul
found 1 day ago
Return flight included
London (LON) to Boston (BOS)
9.6/10 Exceptional! (254 reviews)
The photos doesn’t give this place justice.

Reviewed on 24 Mar 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

Downtown Boston

4.5/5(95 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 £173 per night from 10 May to 11 May
£173
10 May - 11 May
includes taxes & fees
9.6/10 Exceptional! (4,296 reviews)
Loved the location at the Seaport. The staff was helpful in choosing restaurants. They helped me get a great running trail. When it was raining the doorman was great and got me an umbrella before leaving. Breakfast was a good value and tasted good. Cleaning staff was courteous and did a great job. ...

Reviewed on 8 May 2026

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is £167 per night from 10 May to 11 May
£167
10 May - 11 May
includes taxes & fees
9.2/10 Wonderful! (4,638 reviews)
Everything was great except no refrigerator. Maybe I should’ve know that.

Reviewed on 8 May 2026

Omni Boston Hotel at the Seaport
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
505 Washington Street Boston MA
Fully refundableReserve now, pay when you stay
The price is £183 per night from 10 May to 11 May
£183
10 May - 11 May
includes taxes & fees
9.4/10 Exceptional! (5,049 reviews)
Good property.

Reviewed on 7 May 2026

The Godfrey Hotel Boston
See all 4,155 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 £1,197. 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

Fenway Park

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

Fenway Park
Harvard University

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

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 Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

£39
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

£62
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

£25
per adult
88% 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.