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Brookline 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 Brookline vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Breakfast, lunch and brunch served
    Oct 23 - Oct 26

    The Langham, Boston + Flight

    Downtown Boston
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,000 reviews)
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YKF - BOS • 1 stop BOS - YYZ • Nonstop
    CA $2,135
    CA $1,450
    per traveller
    found 2 days ago
    The Langham, Boston
  • Suite, Multiple Beds (John Adams Presidential Suite)
    Oct 23 - Oct 26

    Boston Harbor Hotel + Flight

    North End
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,000 reviews)
    "Neat, clean, and friendly staffing."
    Reviewed July 28, 2026
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YKF - BOS • 1 stop BOS - YYZ • Nonstop
    CA $2,855
    CA $1,504
    per traveller
    found 2 days ago
    Boston Harbor Hotel
  • BRIGHT AND MODERN STUDIO
    Sept 24 - Sept 28

    Good Hotels Boston + Flight

    South End
    4 nights
    2.0 star property
    8.0/10 - 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 May 23, 2026
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • Nonstop BOS - YTZ • Nonstop
    CA $2,507
    CA $1,490
    per traveller
    found 1 day ago
    Good Hotels Boston
  • Terrace/patio
    Oct 23 - Oct 26

    Four Seasons Hotel Boston + Flight

    Bay Village
    3 nights
    5.0 star property
    9.4/10 - Exceptional (474 reviews)
    "perfecto"
    Reviewed June 8, 2026
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YKF - BOS • 1 stop BOS - YYZ • Nonstop
    CA $3,658
    CA $2,245
    per traveller
    found 2 days ago
    Four Seasons Hotel Boston
  • Terrace/patio
    Sept 24 - Sept 28

    The Whitney Hotel + Flight

    Beacon Hill
    4 nights
    4.0 star property
    9.6/10 - Exceptional (598 reviews)
    "It’s our fourth time staying at the Whitney and we love it. Awesome location, awesome property, great service. We’ll be back!"
    Reviewed July 28, 2026
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • Nonstop BOS - YTZ • Nonstop
    CA $3,425
    CA $2,326
    per traveller
    found 1 day ago
    The Whitney Hotel

Where to stay in Brookline

Find the best Brookline areas and neighborhoods for the activities you enjoy most. Learn more about Brookline
Learn more about Brookline
A building with a clock tower, a pointed roof, and a weather vane.

Coolidge Corner South Side

Centered around Beacon and Harvard Streets, this Brookline neighborhood boasts a pedestrian-friendly atmosphere, diverse dining options like crêperies and falafel joints, and cultural gems such as the Art Deco Coolidge Corner Theatre. Easily accessible via the Green Line C branch and #66 bus route.
A cityscape with a prominent train track running down the center of a wide street, surrounded by buildings and greenery.

Washington Square

Washington Square in Brookline balances quiet charm with city access. Tree-lined streets showcase historic homes and early 20th-century architecture. Several synagogues reflect the area's Jewish heritage, while local boutiques and cafes create a welcoming area feel. The Green Line C branch makes exploring Boston a breeze. Diverse restaurants serve Mediterranean, Asian, and American cuisine at reasonable prices. Fenway Park and Harvard Square are just a short train ride away from this authentic residential haven.
A large historic building with a tall tower, a modern high-rise, and an American flag.

North Brookline

North Brookline offers tree-lined streets where historic charm meets cultural diversity. The quiet area showcases beautiful early 20th-century architecture and well-maintained gardens. Visitors can explore the iconic Coolidge Corner Theatre and JFK's birthplace. The area provides a peaceful retreat from Boston's bustle. Excellent public transit connects you to downtown Boston in just 15-20 minutes. Diverse dining options include kosher delis, Asian restaurants, and upscale bistros. Small local shops and boutiques line Beacon Street while nearby Brookline Reservoir offers scenic walking paths for outdoor enthusiasts.

Chestnut Hill

When in Chestnut Hill, you can plan a visit to Chestnut Hill Reservoir and Alumni Stadium, some noteworthy sights in the nearby area.

Coolidge Corner

While you're in Coolidge Corner, take in top sights like Coolidge Corner Theatre or John Fitzgerald Kennedy National Historic Site, and hop on the metro to see more the city at Coolidge Corner Station or Saint Paul St. Station.

Discover the most popular places to visit in Brookline

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 theater scene and fascinating museums in this vibrant area.

What to do in Brookline

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
See all activities in Brookline

Brookline Hotel Deals

Lobby sitting area

Arcadian Hotel

Arcadian Hotel
3.5 star property
1.4 km from Brookline
8.2 out of 10, Very good, (4,322 reviews)
"Terrible check-in experience. They were under-staffed, so what should have been a five-minute process took a full hour of waiting in line, which was not what we wanted when trying to get kids to bed at the end of a travel day. Breakfast selection was limited and ran out quickly. Room got the job done for a two-night stay."
The price is CA $233
CA $307 total
includes taxes & fees
Aug 16 - Aug 17
Arcadian Hotel
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.
See all properties in Brookline

Frequently Asked Questions

How much does a Brookline vacation package cost?

You'll find cheap prices from CA $1,450 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.