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.
Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
8.8/10 Excellent! (2,001 reviews)
Location was perfect.

Reviewed on Jul. 29, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I would say this is one of the best hotel I've stayed in my life!! The room had an amazing harbor view and nice chair, comfortable bed and best amenities!! The stuff was super nice too. Definitely 5 stars!!!

Reviewed on Jul. 28, 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
per person
Sep 14 - Sep 17
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (349 reviews)
This experience from checking in to the quality of the room and the incredible concierge service that helped us with restaurants in our entire experience was unbelievable! It was probably the best experience I had with a luxury hotel in any city I visited. We will definitely be coming back!

Reviewed on Jul. 20, 2025

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
very comfortable suite, lovely staff, great breakfast area

Reviewed on Jul. 25, 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Boston (BOS)
9.6/10 Exceptional! (3,076 reviews)
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Reviewed on Jul. 28, 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 $217 per night from Aug 10 to Aug 11
CA $217
CA $288 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (3,261 reviews)
"We had an incredible stay at The Arcadian Hotel in Brookline! From the moment we arrived, the staff made us feel genuinely welcome—kind, helpful, and always friendly. A special shoutout to Alberto, the manager, who went above and beyond and quickly felt more like a friend than hotel staff. The level ..."

Reviewed on Jul. 28, 2025

The Arcadian Hotel
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 $252 per night from Aug 24 to Aug 25
CA $252
CA $349 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (3,755 reviews)
Outstanding Omni
"Outstanding stay. There’s not one thing that could have been better. I would highly recommend this hotel."

Reviewed on Jul. 27, 2025

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $260 per night from Aug 10 to Aug 11
CA $260
CA $302 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (1,510 reviews)
Hip Hotel!
"Great hotel! It’s a hip and trendy place. The room itself was efficient, clean, comfortable and without unnecessary frills. I really liked the blackout curtain! Was in town for Red Sox games and stayed for one night. It was convenient location to Fenway Park as well as plenty of shops and ..."

Reviewed on Jul. 30, 2025

citizenM Boston Back Bay
See all 3,798 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.
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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

4.5/5(305 reviews)

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

4.5/5(279 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
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

What to do in Brookline

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $108
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $96
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 $46
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 $1,040 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.