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.
The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Price was CA $1,254, price is now CA $761 per person
CA $761
per person
Aug 20 - Aug 23
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (177 reviews)
Great hotel staff, great location, great room :)

Reviewed on Jul 8, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $1,634, price is now CA $1,056 per person
CA $1,056
per person
Aug 31 - Sep 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
From the moment I checked in with Natalie, our 4 days were superb! Natalie was so friendly and explained the property and amenities (our first time there). Even though I researched the property, and am originally from close to Boston, it was the 4th of July weekend, and there was Sooo much going on. Head concierge Nathan provided lots of tips about the best places to see certain events. So helpful. Our room was beautiful and well appointed. I miss the days of the shower cap, sewing kit, slippers, robes, etc. and they provided all that. The bed was extremely comfortable and the housekeeping staff wonderful. We go to Boston a few times a year and will be looking forward to returning here. Fabulous location!

Reviewed on Jul 8, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $1,956, price is now CA $1,320 per person
CA $1,320
per person
Aug 21 - Aug 25
found 19 hours ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
9.6/10 Exceptional! (258 reviews)
Staff was super friendly and accommodating, and we very much enjoyed our stay. Room was good, location is great right on the edge of town and easily accessible.

Reviewed on Jul 8, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $3,502, price is now CA $2,440 per person
CA $2,440
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was CA $2,772, price is now CA $1,957 per person
CA $1,957
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 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
A nighttime street scene with illuminated trees, a market stall, and historic buildings.

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

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
The price is CA $214 per night from Aug 9 to Aug 10
CA $214
CA $291 total
Aug 9 - Aug 10
includes taxes & fees
9/10 Wonderful! (2,433 reviews)
"The restaurant was exceptional"

Reviewed on Jul 9, 2026

Hyatt Regency Boston/Cambridge
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 $268 per night from Jul 26 to Jul 27
CA $268
CA $360 total
Jul 26 - Jul 27
includes taxes & fees
9.6/10 Exceptional! (4,545 reviews)
"The room was comfortable, and clean. I did like the fact you were offered 2 complementary waters. I would definitely stay here again. The location was perfect."

Reviewed on Jul 9, 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 $226 per night from Aug 2 to Aug 3
CA $226
CA $263 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (2,726 reviews)
"Great hotel. Loved the vibe and room was great!"

Reviewed on Jul 8, 2026

The Revolution Hotel
See all 4,126 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 $761. 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.

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $73
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 $119
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 $39
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.