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Holidays to Brookline

Choose two or more items and save on your trip:

Accommodation, flights, car rentals, things to do and more - for your holiday in Brookline choose Expedia! Find everything you need to organise your trip to Brookline in one place. Enter your dates in the search bar above or scroll to our top deals below!

Where to stay in Brookline

Find the best Brookline areas and neighborhoods for the activities you enjoy most. Learn more about Brookline
    Jamaica Plain, Boston, Massachusetts, United States of America

    Jamaica Plain

    4.5/5Wonderful!(3 area reviews)

    Check out the breweries while you're in Jamaica Plain. Hop on the metro at Green Street Station and Stony Brook Station to see top sights like Samuel Adams Brewery and Arnold Arboretum.

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    Kenmore Square featuring street scenes

    Fenway–Kenmore

    4.5/5Wonderful!(27 area reviews)

    Art galleries, museums and historical sites highlight some notable features of Fenway–Kenmore. Make a stop by Fenway Park or Boston Museum of Fine Arts while you're visiting, and jump aboard the metro at Museum of Fine Arts Station or Fenway Station to get around town.

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    Isabella Stewart Gardner Museum showing a city, modern architecture and night scenes

    Medical Center Area

    While you're in Medical Center Area, take in top sights like Isabella Stewart Gardner Museum or Warren Anatomical Museum, and hop on the metro to see more of the city at Longwood Medical Area Station or Brigham Circle Station.

    Find hotels in Medical Center Area
    Jamaica Hills - Pond, Boston, Massachusetts, United States of America

    Jamaica Hills - Pond

    While you're in Jamaica Hills - Pond, take in top sights like Arnold Arboretum and jump on the metro at Back of the Hill Station to see more of the city.

    Find hotels in Jamaica Hills - Pond

Top Hotel Deals

Courtyard by Marriott Boston Brookline
Courtyard by Marriott Boston Brookline
3 out of 5
40 Webster St, Coolidge Corner, Brookline, MA
The price is £92 per night from 1 Mar to 2 Mar

Located in Coolidge Corner South Side, this hotel is within 1 mile (2 km) of Coolidge Corner Theatre, Dana-Farber Cancer Institute and Boston University. Longwood ...…

4.1/5Very Good! (986 reviews)

"easy access, close proximity to buses and shops. Heating was not good in our room."…"

Reviewed on 1 Feb 2021

Courtyard by Marriott Boston Brookline
Homewood Suites by Hilton Boston Brookline-Longwood Medical
Homewood Suites by Hilton Boston Brookline-Longwood Medical
3 out of 5
111 Boylston Street, Brookline, MA
The price is £108 per night from 28 Feb to 1 Mar

Situated in the shopping district, this hotel is within 1 mile (2 km) of Coolidge Corner Theatre, Dana-Farber Cancer Institute and Longwood Medical Area. Brigham ...…

4.4/5Excellent! (384 reviews)
Homeward Suites by Hilton in Boston

"We appreciated the free shuttle service to the local hospitals."…"

Reviewed on 16 Oct 2020

Homewood Suites by Hilton Boston Brookline-Longwood Medical
Beacon Inn 1087
Beacon Inn 1087
2.5 out of 5
1087 Beacon St, Brookline, MA
The price is £70 per night from 1 Mar to 2 Mar

Located in Longwood, this bed & breakfast is within a 10-minute walk of Longwood Medical Area and Boston University. Fenway Park and Beth Israel Deaconess Medical ...…

3.7/5Good! (367 reviews)

"The location is great for my purpose. The room is clean. The shower is a little too small and the bathroom has a big step. I almost tripped on it."…"

Reviewed on 19 Jan 2021

Beacon Inn 1087
See all 2000 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.

Top things to do in Brookline

Image for New England Aquarium Admission

New England Aquarium Admission

£23
Per adult
84% of travellers recommend
New England Aquarium Admission
Image for Go Boston All-Inclusive: 45+ Attractions & Tours on 1 Pass

Go Boston All-Inclusive: 45+ Attractions & Tours on 1 Pass

£48
Per adult
76% of travellers recommend
Go Boston All-Inclusive: 45+ Attractions & Tours on 1 Pass
Image for Boston Historic Sightseeing Cruise

Boston Historic Sightseeing Cruise

£25
Per adult
94% of travellers recommend
Boston Historic Sightseeing Cruise
See all activities in Brookline

Plan your Brookline holiday with Expedia

  • Book your 2021 holiday package deals now! Buy your accommodation, flight or car together and get extra savings on your next trip!
  • We have selected for you amazing deals on incredible hotels in Brookline. Have a look simply by using the search bar above.
  • Most hotels come with free cancellation* , because we believe that flexibility matters now more than ever!

For more information, visit our COVID-19 information page. 
Start browsing now!

*Some hotels require you to cancel at least 24-48 hours before check-in.

Frequently asked questions

If I'm not able to travel, can I cancel my Brookline holiday package?
We totally get that the universe can throw the odd curveball. If you’ve booked a Brookline holiday package and have to change or cancel it, we can help. We recommend having a look at our Customer Service Portal first for information. But generally, if you’ve booked your package in the last 24 hours, you may be able to cancel or change your itinerary for free. If it’s more than 24 hours, your airline, hotel or car rental company may charge a fee.
Where should I stay in Brookline?
Close to the action. Many travellers book hotels within easy reach of top attractions, such as Agganis Arena, Paradise Rock Club and Coolidge Corner Theatre.
What are the top hotels in Brookline?
If it’s your first visit to Brookline, reserve a room at The Inn at Brookline or Courtyard by Marriott Boston Brookline. Both hotels offer comfortable beds and are top options with many savvy travellers.
When is the best time of year to visit Brookline?
There’s a big advantage to holidaying in Brookline in . Usually, you can get the best deals at this time of year. , on the other hand, is the most expensive time to visit. If you love the excitement that comes with peak season, head to Brookline in . The calmer months of will help you avoid the crowds.
How far in advance should I book my Brookline holiday?
It’s difficult to pick the ideal time for airfares, but we normally say the earlier, the better. Plenty of international journeys on Expedia become available to compare up to 12 months in advance. If you’re booking late, don’t despair. Low prices occasionally appear just weeks before departure dates.
What should I know before booking a Brookline travel package?
You’ll land big savings when you combine your flights, hotels and rental cars into a package. Not just that, booking everything together simply makes planning easier. So why waste your money or time? Whether you’re putting together a luxury city stay with your love or a budget family adventure, check out our holiday packages today.
Does Expedia offer Book Now, Pay Later Brookline holiday packages?
If you’re itching for a trip away but can’t afford to cough up the dough, Expedia can help out with a tailored payment plan. Thanks to our partnership with online lender Affirm, you can Book Now, Pay Later and start planning your journey today.