Oak Square Holidays from £991

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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.
Staybridge Suites Burlington Boston, an IHG Hotel

Staybridge Suites Burlington Boston, an IHG Hotel

3 out of 5
per person
23 Jun - 26 Jun
Return flight included
London (LHR) to Boston (BOS)
7.6/10 Good! (1,000 reviews)
Very nice staff. Everybody was extremely pleasant. Nice free social hour food. Hotel a tad run down - but pretty clean overall. HUGE crowd at the breakfast buffet - felt like they were bussed in for breakfast. The breakfast was average...but nice to have. Decent area - felt safe.

Reviewed on 16 May 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
per person
23 Jun - 26 Jun
Return flight included
London (LHR) to Boston (BOS)
9.2/10 Wonderful! (269 reviews)
Amazing rooms, amazing staff, amazing, amazing, amazing.

Reviewed on 16 May 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
8 Aug - 13 Aug
Return direct flight included
London (LON) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
Property was right on the harbor with great views. The hotel was clean with great service and walkable to most attractions

Reviewed on 7 May 2024

Aloft Boston Seaport District

Aloft Boston Seaport District

3 out of 5
Seaport District
per person
23 Jun - 26 Jun
Return flight included
London (LHR) to Boston (BOS)
8.8/10 Excellent! (1,003 reviews)
Valet parking seemed excessive for someone staying there. Nice rooms, very small, not super quiet, appreciated the mini market, showed up very late and kids were hungry. Also there was no hot water in the AM—a nice hotel downtown Boston with only luke warm water.

Reviewed on 15 May 2024

Hampton Inn Boston Seaport District

Hampton Inn Boston Seaport District

3 out of 5
Seaport District
per person
23 Jun - 26 Jun
Return flight included
London (LHR) to Boston (BOS)
9.2/10 Wonderful! (1,298 reviews)
Hospitable, well lit and clean.

Reviewed on 16 May 2024

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

Four Points by Sheraton Boston Newton
Four Points by Sheraton Boston Newton
3.5 out of 5
320 Washington Street, Newton, MA
The price is £108 per night from 27 May to 28 May
£108
per night
27 May - 28 May
8/10 Very Good! (2,038 reviews)
Room temperature not comfortable
"Room was very hot, despite our thermostat being set to 60 degrees AC. Smelled like someone smoked in the room prior to us."

Reviewed on 14 May 2024

Four Points by Sheraton Boston Newton
Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is £204 per night from 9 Jun to 10 Jun
£204
per night
9 Jun - 10 Jun
9/10 Wonderful! (2,049 reviews)
"The staff was friendly. Our room was super clean, comfy, and had a great view of the city. I loved the floor to ceiling windows."

Reviewed on 14 May 2024

Omni Boston Hotel at the Seaport
The Dagny Boston
The Dagny Boston
4 out of 5
89 Broad Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is £212 per night from 27 May to 28 May
£212
per night
27 May - 28 May
9.2/10 Wonderful! (3,500 reviews)
Perfect!
"Clean, friendly staff, excellent location to everything!"

Reviewed on 13 May 2024

The Dagny Boston
See all 3,168 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 £991. 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

Image for Fenway Park

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
Image for Harvard University

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
Image for New England Aquarium

New England Aquarium

4.5/5(57 reviews)

From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips.

New England Aquarium

Things to do

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

£63
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Image for Bewitched Walking Tour of Salem

Bewitched Walking Tour of Salem

£24
Per adult
100% of travellers recommend
Bewitched Walking Tour of Salem
Image for Odyssey Boston Premier Elegant Dinner Cruise

Odyssey Boston Premier Elegant Dinner Cruise

£154
Per adult
Odyssey Boston Premier Elegant Dinner Cruise
See all activities in Boston

More trip options

* 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.