Oak Square Holidays

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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 showing a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(17 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

Our pick of the best Oak Square Hotel Deals

citizenM Boston North Station

citizenM Boston North Station

4 out of 5
70 Causeway Street Boston MA
Fully refundableReserve now, pay when you stay
The price is NZ$285 per night from 15 Dec to 16 Dec
NZ$285
15 Dec - 16 Dec
includes taxes & fees
9.2/10 Wonderful! (4,037 reviews)
I had an absolutely wonderful experience during my stay. From the moment I arrived, the staff made me feel welcomed and taken care of. Check-in was quick and easy, and every team member I encountered was friendly, professional, and genuinely eager to help. The room was spotless, beautifully designed, ...

Reviewed on 14 Nov 2025

citizenM Boston North Station
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 NZ$382 per night from 30 Nov to 1 Dec
NZ$382
30 Nov - 1 Dec
includes taxes & fees
9/10 Wonderful! (4,208 reviews)
Christina D at check in was outstanding!

Reviewed on 16 Nov 2025

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 NZ$137 per night from 24 Nov to 25 Nov
NZ$137
24 Nov - 25 Nov
includes taxes & fees
9/10 Wonderful! (2,250 reviews)
I gave a 5 stars for breakfast but i honestly didnt have any here. Im not sure if they even offer it BUT i didnt want to lower stars because of that. The hotel was super clean and colourful! The front desk people were AMAZING. Super easy check in and out. Our blinds werent working in our room and ...

Reviewed on 17 Nov 2025

The Revolution Hotel
See all 3,840 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.

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.

Discover the most popular places to visit in Oak Square

Fenway Park which includes night scenes and a sporting event as well as a large group of people

Fenway Park

The iconic home of the Boston Red Sox is on the must-see list of every red-blooded baseball fan.

Fenway Park
Harvard University which includes heritage architecture and a city

Harvard University

You don’t have to be a history student to appreciate the unique heritage of this world-renowned academic institution.

Harvard University
TD Garden

TD Garden

Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area.

TD Garden

Activities

View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

NZ$59
per adult
86% of travellers recommend
View Boston Observation Deck Admission Tickets
Boston Freedom Trail Walking Tour with Costumed Guide

Boston Freedom Trail Walking Tour with Costumed Guide

NZ$45
per adult
94% of travellers recommend
Boston Freedom Trail Walking Tour with Costumed Guide
Whale-Watching Cruise in Stellwagen Bank Marine Sanctuary

City Cruises: Boston Harbor New England Aquarium Whale-Watching Cruise

NZ$149
per adult
86% of travellers recommend
City Cruises: Boston Harbor New England Aquarium Whale-Watching Cruise
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.