Oak Square Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Our guide on 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
Take a walk through the charming streets, historic buildings and small-town 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 New England Aquarium while you're visiting, and jump aboard the metro at Aquarium to get around town.
Our pick of the best Oak Square Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
NZ$603
6 Sept - 7 Sept
includes taxes & fees
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
NZ$325
10 Sept - 11 Sept
includes taxes & fees
Encore Boston Harbor
1 Broadway Everett MA
Fully refundableReserve now, pay when you stay
NZ$541
21 Sept - 22 Sept
includes taxes & fees
9.6/10 Exceptional! (4,137 reviews)
"The room and the price were amazing highly recommend"
Reviewed on 31 Aug 2026
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 holiday package cost?
From just . Yes, you read that right. Our Oak Square packages are an awesome way to make your budget last longer. Combine your preferred hotels, flights and car rentals and explore this fabulous destination.
How do I get a cheap travel package to Oak Square?
Bundle your hotel and flight bookings, toss in extras such as tours, and save with an Oak Square holiday package. You won't just pick up amazing discounts on your trip — you'll have loads of choice within your reach too. When you book through Expedia, you'll have your pick of over 550 airlines and 1 000 000 properties around the world. Your next affordable adventure starts right here, right now!
Where should I stay in Oak Square?
Urban adventurers come from all corners of the globe to see Fenway Park and TD Garden in Oak Square. Book a room close to these popular attractions to make sightseeing easy.
What are the top hotels in Oak Square?
If it's comfort and convenience you want, you can't go past Luxurious Urban Oasis With Patio And Free Parking. Spend your nights relaxing here and your days wandering around Oak Square's finest sights.
How far in advance should I book my Oak Square holiday?
Travellers are generally able to browse international fares on Expedia up to 12 months prior to departure. Booking late? With a stroke of luck, it's still possible to nab a cheaper ticket only weeks before your journey.
What does an Expedia Oak Square travel package include?
Flights, hotels and rental cars, or any combination of the three — the choice is all yours! Whether you're exploring Oak Square with the family or adventuring solo, there's a bundle to suit every style and budget. Once you've made your booking, why not add on a couple of activities?
What should I know before booking an Oak Square travel package?
You can save a tidy sum by combining your airfares, hotels and rental cars. Once you've created your package, you can add on things like tours and activities. Your next awesome holiday is only a few clicks away.
Can I choose my airline with an Oak Square Expedia holiday package?
Yes, and with over 550 airlines to pick from globally, it's all about choice. Have a look through the available options and find out which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Oak Square holiday package?
It's good to know that you can cancel your Oak Square booking if your travel plans have been upended. Whether you'll incur a fee or not depends on your hotel, airline or car rental company. You may be able to cancel or change your booking for free if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.
Activities
Boston Old Town Trolley Hop-on Hop-Off City Tour
NZ$82
per adult
90% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
NZ$119
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
NZ$77
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.