Brookline Vacation Packages

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Your Brookline Vacation

Reserve a Brookline vacation package and prepare to experience the best of this lively city. Consider staying in the neighborhood of Downtown Boston, which is great for nightlife, shopping and bars and pubs. If a sightseeing tour is part of the plan during your trip to Brookline, look around major attractions like Fenway Park, Boston Common and Boston Museum of Fine Arts. Don't put off your visit to this destination any longer. The ultimate Brookline vacation is just a few clicks away with Expedia.

Top Brookline Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Lakeside Inn

Lakeside Inn

2 out of 5
Price was CA $1,094, price is now CA $703 per person
CA $703
per person
Oct 29 - Nov 3
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
7.4/10 Good! (2,162 reviews)
We stayed for one night. When we arrived the restaurant was just jumping with excitement with families and others singing karaoke. It was a nice welcome. We checked out the pool. It was a little cold but the kids had a quick dip and were happy. The staff was amazing. Such great customer service. From the staff that checked us in, the gentleman that cooked breakfast and the lady that cleaned the rooms. The maintenance man helped us with a little issue faster than my toddler could asking him a million questions which is lightning speed. Checkout was also great! 10/10 would definitely stay here again. Rooms were comfortable, quiet, and clean! Great water pressure for the kids baths and showers.

Reviewed on Aug. 28, 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was CA $1,625, price is now CA $956 per person
CA $956
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (490 reviews)
Love the Street Bar!

Reviewed on Aug. 25, 2025

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Price was CA $1,893, price is now CA $1,160 per person
CA $1,160
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTZ) to Boston (BOS)
8.8/10 Excellent! (1,003 reviews)
10 mins to Fenway - was a great place.

Reviewed on Aug. 27, 2025

Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
Price was CA $2,403, price is now CA $1,539 per person
CA $1,539
per person
Oct 13 - Oct 18
found 5 hours ago
Roundtrip flight included
Vancouver (YVR) to Boston (BOS)
8.6/10 Excellent! (1,098 reviews)
Great spot. Friendly helpful staff.

Reviewed on Aug. 25, 2025

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St

2 out of 5
Back Bay
Price was CA $1,728, price is now CA $1,163 per person
CA $1,163
per person
Oct 29 - Nov 3
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very Good! (139 reviews)
Clean. Great location.

Reviewed on Jul. 31, 2025

Where to stay in Brookline

Find the best Brookline areas and neighborhoods for the activities you enjoy most. Learn more about Brookline
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Chestnut Hill

1 out of top 10 points of interest in this area

Well-liked for its restaurants and sporting events, Chestnut Hill is worth a visit. Check out the variety of things to see and do like Alumni Stadium and Chestnut Hill Reservoir, and jump on the metro at Chestnut Hill Station to get around the city.

Find hotels in Chestnut Hill

Ready to book your vacation to Brookline?

 

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Brookline Hotel Deals

The Arcadian Hotel

The Arcadian Hotel

3.5 out of 5
1200 Beacon St, Brookline, MA
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Sep 1 to Sep 2
CA $197
CA $266 total
Sep 1 - Sep 2
includes taxes & fees
The Arcadian Hotel
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 $213 per night from Sep 1 to Sep 2
CA $213
CA $255 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (3,276 reviews)
"Clean comfortable room with massive comfy bed. Very conveniently situated for the cruise port. Staff were extremely professional, friendly and helpful."

Reviewed on Aug. 25, 2025

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $294 per night from Sep 1 to Sep 2
CA $294
CA $399 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (3,870 reviews)
"We stayed for a couple of days at the end of our trip to Boston, the hotel was perfect for relaxing by the pool and a short walk from all the areas we wanted to see whilst visiting."

Reviewed on Aug. 25, 2025

Omni Boston Hotel at the Seaport
See all 3,796 properties in Brookline
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
Family Vacations
Family Vacations

Discover the most popular places to visit in Brookline

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

Fenway Park

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

Fenway Park
Harvard University which includes a city and heritage architecture

Harvard University

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common which includes flowers, a garden and landscape views

Boston Common

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

What to do in Brookline

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $109
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $97
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

CA $47
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Brookline

Frequently asked questions

How much does a Brookline vacation package cost?
You'll find cheap prices from CA $703 on Expedia for your Brookline getaway. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Brookline costs.
What are the cheapest months to go to Brookline?
December, January and February are great times to look for cheap Brookline vacation packages. Choosing to travel in less busy periods means you'll typically find reduced prices on accommodations and flights.
How many days is enough for Brookline?
We'd recommend booking a Brookline vacation for a minimum of 3 days. This will give you enough time to visit key attractions such as Boston Common and Copley Square, as well as explore neighbourhoods like South Boston and D Street - West Broadway. You could even make time for a day trip or two outside of Brookline.
Is it worth booking a vacation package to Brookline?
Brookline has everything you need for an amazing getaway. Begin your Brookline vacation on a high note by visiting top attractions like Agganis Arena.
How to find the best Brookline package deals?
Use Expedia's filters to find some tempting Brookline package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Brookline package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Brookline vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging accommodations and flights individually. Better still, you can customize your Brookline trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Brookline?
If you're considering a spontaneous Brookline adventure, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Brookline?

  1. Choose your dates: The things you'd like to do in Brookline and your favourite season will help you decide when to get away.
  2. Budget wisely: As well as the price of your accommodations, you'll need to factor in other expenses. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that could crop up during your trip to Brookline.
  3. Decide how long to go away for: Now that you're up to speed on Brookline, you can work out the perfect length of your vacation. Create a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Brookline vacation package that brings all your bookings together.

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