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.
Boston Lodge and Suites
Dorchester
CA $665
per person
Sep 7 - Sep 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
Pier 7 Condominiums
Bass River
CA $854
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
8.6/10 Excellent! (13 reviews)
I loved this place so much! The place was extremely clean and I felt very comfortable during my stay. The air conditioning ran super cold, the kitchen provided most things needed to make a quick meal, and the pool was very comfortable. They also have games and ping pong available.
Reviewed on Aug 6, 2026
By the Sea Guests Bed & Breakfast & Suites
CA $700
per person
Oct 26 - Oct 29
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (203 reviews)
Gorgeous location, room and common areas with lots of historic charm mixed with thoughtful touches throughout. Lovely to have the well-kept private beach all set up and ready to enjoy. Room was bright and cheerful and breakfast was delicious as well. If you’re looking for peaceful and quiet, this is a great choice.
Reviewed on Aug 7, 2026
Sesuit Harbor House
CA $987
per person
Sep 16 - Sep 20
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (196 reviews)
The Sesuit Harbor House is awesome. Has a very Cape Cod feel, the owners are excellent very attentive and have done an awesome job with this property. There is a beautiful fire pit, pool, nice outside areas to eat and relax and they also have goats! I highly recommend, close to dining and beaches as well.
Reviewed on Aug 1, 2026
The Mansion at Ocean Edge
CA $2,979
per person
Sep 16 - Sep 20
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very good! (1,004 reviews)
Hotel and Expedia canceled my booking last minute and I had to spend 3 hours on call to get alternate booking. I paid same high price for something that was much less than my original booking. Last minute cancelation of hotel bookings is extremely disappointing, especially if it's in middle of vacation. There should be binding cancelation policy for hotels as well.
Reviewed on Jul 30, 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
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.
Back Bay
1 out of top 10 points of interest in this area
Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower.
Seaport District
Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge.
Beacon Hill
1 out of top 10 points of interest in this area
Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations.
North End
1 out of top 10 points of interest in this area
Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries.
Oak Square Hotel Deals
Seaport Hotel Boston
1 Seaport Lane Boston MA
CA $265
CA $356 total
Aug 30 - Aug 31
includes taxes & fees
9.6/10 Exceptional! (4,688 reviews)
"Room service would be useful and a better stocked convenience store within the hotel is needed."
Reviewed on Aug 6, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $191
CA $222 total
Sep 7 - Sep 8
includes taxes & fees
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
CA $335
CA $448 total
Aug 20 - Aug 21
includes taxes & fees
9.2/10 Wonderful! (4,861 reviews)
"The Omni was overall a fantastic hotel to stay in. The location was great. The staff was very approachable and friendly. There was always someone there to help. It was convenient to have restaurants on site as well as 24 hour room service. We stayed in an artist king studio. The room was clean and ..."
Reviewed on Aug 6, 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 vacation package cost?
From just CA $665. 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.
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $72
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $118
per adult
92% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
CA $65
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.