Oak Square Vacations from $341

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Your Oak Square Vacation

Oak Square is beckoning! Whatever type of break you have in mind, get ready to discover the best of this neighborhood with an Oak Square vacation package. Your trip to Oak Square wouldn't be complete without exploring top attractions nearby such as Harvard Square, Harvard University and Boston College. Stop dreaming and start doing. When you're ready to book your ideal vacation to Oak Square, Expedia is here to help.

The Latest Oak Square Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sea Mist Resort by VRI Americas

Sea Mist Resort by VRI Americas

3 out of 5
Save 100% on your flight
per person
Nov 8 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8.8/10 Excellent! (99 reviews)
Check in was easy and we got to check in at 3:30pm. Our room was large, kitchen, LR, 2 baths, BR and deck. It was very quiet, clean, and the bed was comfortable. No coffee is available in the room, or shampoo/conditioner. Only gripe was before leaving we got calls in the room and on our cell to get out. Check out is 10am...most are 11am. The resort was pretty much empty so it wasn't like they needed the room asap. I've never had this happen and didn't appreciate the calls.

Reviewed on Sep 16, 2024

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Dec 6 - Dec 10
found 2 days ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.6/10 Excellent! (1,001 reviews)
It the most beautiful hotel I've ever seen. It has so much charter amazing detail to the wood work.

Reviewed on Sep 17, 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Nov 21 - Nov 25
found 9 hours ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
9.6/10 Exceptional! (56 reviews)
Amazing hotel. The hotel staff were very helpful, attentive to detail and professional. The staff at the Long Bar and Terrace were a different story. We got a table in the evening and no one ever came to us, we ended up standing by the bar and just ordering a drink there. For breakfast, we placed our order and apparently we were forgotten. I had to get up and go look for a staff member. The room was great, but we found body hair in the tub as we arrived. It was taken care of but something to keep in mind.

Reviewed on Sep 13, 2024

Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
Save 100% on your flight
per person
Nov 8 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8.8/10 Excellent! (1,168 reviews)
Great location in the cape. The hotel has a beautiful view of the salt marsh in the back. A very important detail for me is that it has EV charging available. Overall a basic hotel that checks all the marks to enjoy your stay

Reviewed on Sep 16, 2024

The Boxer

The Boxer

4 out of 5
West End
Save 100% on your flight
per person
Dec 6 - Dec 10
found 2 days ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.6/10 Excellent! (1,004 reviews)
Walking distance to some of the oldest bars in America. A lot of really good shopping and restaurants also walking distance.

Reviewed on Sep 18, 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(2,415 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

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 $293 per night from Sep 22 to Sep 23
$293
includes taxes & fees
$252 per night
Sep 22 - Sep 23
9.2/10 Wonderful! (4,558 reviews)
"Ideal location very friendly staff"

Reviewed on Sep 19, 2024

The Dagny Boston
Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
The price is $302 per night from Sep 22 to Sep 23
$302
includes taxes & fees
$259 per night
Sep 22 - Sep 23
9/10 Wonderful! (2,758 reviews)
"the pillows were very soft and the memory foam pillows provided were also soft."

Reviewed on Sep 20, 2024

Omni Boston Hotel at the Seaport
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 $296 per night from Sep 22 to Sep 23
$296
includes taxes & fees
$254 per night
Sep 22 - Sep 23
8.8/10 Excellent! (2,769 reviews)
"Great reception staff"

Reviewed on Sep 17, 2024

Omni Parker House
See all 3,122 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does an Oak Square vacation package cost?
From just $341. 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(2,499 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(1,966 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 Boston Common

Boston Common

4.5/5(4,786 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

Things to do

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$74
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Image for Boston Duck Boat Sightseeing City Tour with Cruise Along Charles River

Boston Duck Boat Sightseeing City Tour with Cruise Along Charles River

$58
Per adult
90% of travellers recommend
Boston Duck Boat Sightseeing City Tour with Cruise Along Charles River
Image for Sunset Cruise

Sunset Cruise

$29
Per adult
80% of travellers recommend
Sunset Cruise
See all activities in Boston

Other vacations you might like

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