Coolidge Corner South Side Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Coolidge Corner South Side

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

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,860, price is now CA $1,934 per person
CA $1,934
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (1,007 reviews)
Right in heart of town

Reviewed on May 12, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $4,313, price is now CA $2,603 per person
CA $2,603
per person
Jun 25 - Jul 2
found 6 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (255 reviews)
Splendid bed and breakfast

Reviewed on Apr 29, 2026

Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Price was CA $3,164, price is now CA $1,954 per person
CA $1,954
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
8.4/10 Very Good! (1,441 reviews)
Friendly staff clean room good location

Reviewed on May 14, 2026

Nantucket Inn

Nantucket Inn

3.5 out of 5
Price was CA $3,606, price is now CA $2,485 per person
CA $2,485
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (676 reviews)
Clean, friendly staff, nice indoor pool, good breakfast sanwich

Reviewed on May 12, 2026

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Price was CA $3,358, price is now CA $2,341 per person
CA $2,341
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (3,741 reviews)
my breakfast was wounderfull

Reviewed on May 14, 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

Downtown Boston

4.5/5(197 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

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 $318 per night from May 25 to May 26
CA $318
CA $417 total
May 25 - May 26
includes taxes & fees
9.6/10 Exceptional! (4,345 reviews)
Everyone was so welcoming, so accommodating, so conveniently located—the highest recommendation.

Reviewed on May 15, 2026

Seaport Hotel 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 $174 per night from May 25 to May 26
CA $174
CA $202 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (2,606 reviews)
Real Cool Spot, Nice Amenities

Reviewed on May 15, 2026

The Revolution Hotel
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 CA $241 per night from May 29 to May 30
CA $241
CA $336 total
May 29 - May 30
includes taxes & fees
9.2/10 Wonderful! (4,646 reviews)
Such a beautiful hotel. The room was super clean. Parking was easy. Will definitely stay again

Reviewed on May 15, 2026

Omni Boston Hotel at the Seaport
See all 4,153 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.
All Inclusive Vacations
All Inclusive Vacations
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Beach Vacations
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Family Vacations

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 $1,934. 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

Fenway Park

4.5/5(310 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University

Harvard University

4.5/5(284 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
Gillette Stadium

Gillette Stadium

4.5/5(28 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

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $79
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 $115
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $47
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
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.