Oak Square Holidays from £1,059

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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 Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Save 100% on your flight
Price was £1,632, price is now £1,059 per person
£1,059
per person
25 Mar - 1 Apr
found 1 day ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
9.2/10 Wonderful! (2,268 reviews)
Easy check in, courteous staff, clean rm and great view. Prudential mall across Huntington Ave..

Reviewed on 2 Feb 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was £3,148, price is now £2,055 per person
£2,055
per person
2 Apr - 9 Apr
found 1 day ago
Return direct flight included
London (LHR) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on 25 Jan 2026

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was £2,214, price is now £1,491 per person
£1,491
per person
25 Mar - 1 Apr
found 1 day ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
Entire staff was very professional. Room was clean. The entire experience, including Valentine's dinner at the Peregrin was exceptional. We will be staying there again on our next trip to Boston.

Reviewed on 16 Feb 2026

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 £1,760, price is now £1,198 per person
£1,198
per person
25 Mar - 1 Apr
found 1 day ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
9.6/10 Exceptional! (247 reviews)
Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room.

Reviewed on 21 Oct 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was £2,819, price is now £2,005 per person
£2,005
per person
25 Mar - 1 Apr
found 1 day ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
Room was excellent. Large, clean? Beautiful amenities and furniture. Great location with plenty to choose for food and entertainment. Staff were outstanding and friendly. The lobby with the flowers and spiral staircase was stunning

Reviewed on 15 Feb 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 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

Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is £84 per night from 22 Feb to 23 Feb
£84
22 Feb - 23 Feb
includes taxes & fees
9.2/10 Wonderful! (6,284 reviews)
The hotel is wonderful and in a great location. I had a problem through the booking site and when they reached out to the hotel you were very accommodating. Thank you.

Reviewed on 17 Feb 2026

Harborside Inn Of 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 £137 per night from 22 Feb to 23 Feb
£137
22 Feb - 23 Feb
includes taxes & fees
9/10 Wonderful! (4,477 reviews)
Staff was amazing

Reviewed on 16 Feb 2026

Omni Boston Hotel at the Seaport
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 £83 per night from 22 Feb to 23 Feb
£83
22 Feb - 23 Feb
includes taxes & fees
9/10 Wonderful! (2,467 reviews)
Clean room and bathroom. Very comfortabke bed. Efficient temperature control. Kind service and prices that rocked.

Reviewed on 16 Feb 2026

The Revolution Hotel
See all 4,121 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 £1,059. 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

4.5/5(61 reviews)

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

Fenway Park
Boston Common which includes a skyscraper, landscape views and a park

Boston Common

4.5/5(204 reviews)

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
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(102 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

£38
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

£58
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

£17
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
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.