Coolidge Corner South Side Vacation Packages

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Top Holiday Package Deals in Coolidge Corner South Side

Price found within the past 48 hours. Click for updated prices.
Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
Price was CA $1,221, price is now CA $856 per person
CA $856
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.6/10 Excellent! (1,175 reviews)
Staff was friendly. Room was clean

Reviewed on Feb 5, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,075, price is now CA $1,643 per person
CA $1,643
per person
Apr 29 - May 2
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was CA $2,842, price is now CA $1,711 per person
CA $1,711
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Room very well appointed and gym was the stand out

Reviewed on Jan 25, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,582, price is now CA $1,072 per person
CA $1,072
per person
Mar 20 - Mar 23
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Perfect service, quite classic luxury hotel. We had a perfect stay and look forward to our next stay. Thank you

Reviewed on Feb 3, 2026

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Price was CA $1,302, price is now CA $887 per person
CA $887
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,000 reviews)
Staff was great we were treated with warm chocolate chip cookies. but Expedia told us breakfast was included and that was a lie

Reviewed on Feb 2, 2026

Where to stay in Coolidge Corner South Side

Find the best Coolidge Corner South Side areas and neighborhoods for the activities you enjoy most. Learn more about Coolidge Corner South Side
Downtown Boston showing a city and night scenes 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 hotels in Downtown Boston

Coolidge Corner South Side Hotel Deals

Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Feb 22 to Feb 23
CA $138
CA $217 total
Feb 22 - Feb 23
includes taxes & fees
8.2/10 Very Good! (3,113 reviews)
The hotel itself is beautiful. The lobby is grand with a vibrant bar, restaurant in the center. The staff is friendly. This was a weekend away for me and my 10 year old daughter and we wanted something luxurious. Since it was so cold outside I knew we were going to be in the room a lot. I know the ...

Reviewed on Feb 6, 2026

Hilton Boston Park Plaza
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is CA $146 per night from Feb 16 to Feb 17
CA $146
CA $171 total
Feb 16 - Feb 17
includes taxes & fees
9.2/10 Wonderful! (6,199 reviews)
Best price for the location! Always clean and great staff!

Reviewed on Feb 4, 2026

Harborside Inn Of Boston
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 CA $88 per night from Feb 9 to Feb 10
CA $88
CA $102 total
Feb 9 - Feb 10
includes taxes & fees
9/10 Wonderful! (2,451 reviews)
I stayed in a loft on the side of the main hotel, and it was extremely spacious with all the amenities I needed. It was definitely worth the price, especially given the beautiful area it’s located in. I didn’t interact much with the staff, but the few interactions I had were very pleasant. I would ...

Reviewed on Feb 7, 2026

The Revolution Hotel
See all 4,094 properties in Coolidge Corner South Side
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.
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Frequently asked questions

How much does a Coolidge Corner South Side vacation package cost?
We make it simple to see the world, with Coolidge Corner South Side vacation packages starting from as little as CA $856. You'll have the flexibility to combine your favorite hotels, airlines and car rental. For the ultimate escape, why not add some tours and activities to your travel itinerary?
How do I get a cheap travel package to Coolidge Corner South Side?
Bundle your bookings with Expedia to save big bucks on your next exciting adventure. With more than 550 partner airlines and 1,000,000 hotels across the globe, your Coolidge Corner South Side vacation package can be customized exactly to suit your travel style. With all those extra dollars, why not add some exciting tours and activities? It's an easy way to unlock even more savings. Your dream vacation in Coolidge Corner South Side is closer than you thought!
Where should I stay in Coolidge Corner South Side?
With fascinating attractions like Coolidge Corner Theatre and John Fitzgerald Kennedy National Historic Site in this area, see if you can find a hotel near either one. Larz Anderson Auto Museum is another sight in Coolidge Corner South Side that draws in the crowds.
What are the top hotels in Coolidge Corner South Side?
Book a stay at Coolidge Corner Guest House. It's one of the neighborhood's most popular properties. Another top option in Coolidge Corner South Side is Courtyard by Marriott Boston Brookline.
How far in advance should I book my Coolidge Corner South Side vacation?
While not all airlines advertise ticket prices early, you can normally compare international airfares on Expedia up to 12 months in advance. This is when you'll nab some incredible deals. If you've left everything to the last minute, you may still be in luck. Discounted prices occasionally appear only weeks prior to departure.
What does an Expedia Coolidge Corner South Side travel package include?
That depends on what you're looking for. If you're traveling alone, you might decide to combine flights and hotels. Taking the whole crew to Coolidge Corner South Side? A travel package including hotels, flights and rental cars might be a better fit. Expedia gives you the freedom and flexibility to build your own travel package.
What should I know before booking a Coolidge Corner South Side travel package?
Bundling your bookings into a Coolidge Corner South Side vacation package is the easiest way to organize your trip. Not only that, you'll save big when you combine your flights, hotels and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with a Coolidge Corner South Side Expedia vacation package?
With a vacation package, the choice is in your hands. Whether you're looking to fly to Coolidge Corner South Side in business or coach, simply select from the available airline options. Expedia has access to more than 550 airline partners throughout the world.
If I'm not able to travel, can I cancel my Coolidge Corner South Side vacation package?
It's hard to predict what the future holds, so it's good to know that you can change or cancel your Coolidge Corner South Side vacation package. If you booked in the last 24 hours, you may be entitled to a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to find out more.

Discover the most popular places to visit in Coolidge Corner South Side

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

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
Gillette Stadium is also home to the New England Revolution, our pro soccer team. Tickets are easy to get and not crazy expensive. And there is always a section reserved for the hooligans, who keep the energy up for the whole stadium!

Gillette Stadium

4.5/5(27 reviews)

Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theater scene and great live music.

Gillette Stadium
Boston Common which includes flowers, a garden and landscape views

Boston Common

4.5/5(518 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

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

CA $72
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $108
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

CA $31
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
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.