Oak Square Vacation Packages

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Top Holiday Package Deals in Oak Square

Price found within the past 48 hours. Click for updated prices.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Aug. 9 - Aug. 12
found 6 hours ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (1,003 reviews)
Everything was excellent (restaurants, walking, safety) you name it - it felt like a dream vacation!

Reviewed on May 28, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Jul. 2 - Jul. 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
This is an upscale hotel with excellent amenities and wonderfully helpful and friendly people who kindly made our stay a joy.

Reviewed on May 27, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug. 9 - Aug. 12
found 6 hours ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.2/10 Wonderful! (270 reviews)
Awesome, awesome, awesome. I could not find another word to describe my stay! Awesome.

Reviewed on May 22, 2024

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Aug. 9 - Aug. 12
found 6 hours ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (276 reviews)
The Whitney is an absolute jewel. We had a wonderful stay in a gorgeous room in an ideal location. The staff is extremely courteous and helpful and everything was immaculately clean. The rooms are perfectly appointed and it felt as though all of the details from toiletries to the clothes steamer were curated. The beds and pillows were extremely comfortable. We loved the convenience of the location with so much walkability and beautiful paths behind the hotel on the water. We will definitely stay at the Whitney again!

Reviewed on May 17, 2024

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Aug. 1 - Aug. 5
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (153 reviews)
From the moment we walked into the lobby at Beacon Hill Hotel we were greeted and treated like VIPs. The room, was a corner, looking out over Charles Street. Perfectly comfortable and artfully appointed. My only complaint and this is silly the pillows too puffy. We dined there as well and the food and service was superb.

Reviewed on May 23, 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 night scenes and a city as well as a small group of people

Downtown Boston

4.5/5(193 area reviews)

Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.

Find hotel + flight trips in Downtown Boston

Oak Square Hotel Deals

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 CA $324 per night from Jun. 28 to Jun. 29
CA $324
CA $417 total
includes taxes & fees
Jun 28 - Jun 29
9/10 Wonderful! (2,093 reviews)
"Very welcoming hotel for everyone. Very clean. Walking distance to seaport. We’ll be back."

Reviewed on May 27, 2024

Omni Boston Hotel at the Seaport
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 CA $367 per night from Jun. 16 to Jun. 17
CA $367
CA $434 total
includes taxes & fees
Jun 16 - Jun 17
9.6/10 Exceptional! (2,167 reviews)
"Surprisingly up-to-date, extremely first class. Perfect location - Will stay there whenever I return to Boston!"

Reviewed on May 25, 2024

Seaport Hotel Boston
Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $303 per night from Jun. 16 to Jun. 17
CA $303
CA $400 total
includes taxes & fees
Jun 16 - Jun 17
8.8/10 Excellent! (2,669 reviews)
"Historic property in a fantastic location. Our basic king room was small but clean, quiet, and comfortable. The staff were fantastic."

Reviewed on May 27, 2024

Omni Parker House
See all 3,172 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Oak Square vacation package cost?
From just CA $1,133. 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 vacation 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 vacation?
Travelers 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 vacation is only a few clicks away.
Can I choose my airline with an Oak Square Expedia vacation 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 vacation 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

Image for Fenway Park

Fenway Park

4.5/5(305 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(279 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(154 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

CA $107
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

CA $41
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

CA $264
Per adult
Odyssey Boston Premier Elegant Dinner Cruise
See all activities in Boston

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.