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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,449, price is now CA $656 per person
CA $656
per person
Dec 11 - Dec 14
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Boston (BOS)
8.4/10 Very good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,208, price is now CA $1,261 per person
CA $1,261
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Price was CA $2,707, price is now CA $1,717 per person
CA $1,717
per person
Dec 11 - Dec 14
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Boston (BOS)
9.4/10 Exceptional! (465 reviews)

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,633, price is now CA $1,679 per person
CA $1,679
per person
Dec 11 - Dec 14
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,198, price is now CA $1,506 per person
CA $1,506
per person
Dec 11 - Dec 14
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)

Ready to book your vacation to Brookline?

 

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Brookline Hotel Deals

Arcadian Hotel

Arcadian Hotel

3.5 out of 5
1200 Beacon St Brookline MA
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Nov 26 to Nov 27
CA $150
CA $214 total
Nov 26 - Nov 27
includes taxes & fees
Arcadian Hotel
Iris Hotel Boston

Iris Hotel Boston

4 out of 5
30 Webster St Brookline MA
Fully refundableReserve now, pay when you stay
The price is CA $216 per night from Dec 1 to Dec 2
CA $216
CA $242 total
Dec 1 - Dec 2
includes taxes & fees
Iris Hotel Boston
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 $219 per night from Nov 22 to Nov 23
CA $219
CA $311 total
Nov 22 - Nov 23
includes taxes & fees
9.2/10 Wonderful! (4,952 reviews)
"Great hotel in the great neighborhood"

Reviewed on Oct 30, 2026

Omni Boston Hotel at the Seaport
See all 4,164 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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Stay near popular Brookline attractions

A narrow alley with brick buildings, colorful outdoor seating, and a brightly lit sign.
Photo by Din Kime
Open Photo by Din Kime

Coolidge Corner Theatre

8.6/10 (38 reviews)
Get tickets for a show at Coolidge Corner Theatre, a storied theater in Brookline. Experience the acclaimed art scene and fascinating museums in this vibrant area.
See properties

What to do in Brookline

Boston Hop-On Hop-Off Trolley Tour

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

CA $69
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
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

CA $65
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
See all activities in Brookline

Frequently asked questions

How much does a Brookline vacation package cost?
You'll find cheap prices from CA $656 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.

Explore a world of travel with Expedia

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