Brookline Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

Photo by Ed Gaffny

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ฿4,531 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Brookline

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

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

Top hotels in Brookline

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 ฿4,869 per night from 10 Aug to 11 Aug
฿4,869
฿6,523 total
10 Aug - 11 Aug
includes taxes & fees
8/10 Very Good! (3,283 reviews)
"a 25 min powerwalk to fenway. Neighborhood very safe to walk at night. a 10 min walk opposite direction for a street that has multiple restaurant to choose from. Its a 15-20 min uber ride away to TD garden and freedom trail. I stayed 2 different rooms, since I extended my stay. My first room no phone ..."

Reviewed on 6 Aug 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 ฿5,917 per night from 24 Aug to 25 Aug
฿5,917
฿8,207 total
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (3,785 reviews)
"Overall the stay was wonderful. Room was fabulous with a great view and atmosphere. Only problem was valet parking. Car was waiting for me as expected but the guy for valet was missing in action even though I was the only person waiting."

Reviewed on 6 Aug 2025

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ฿5,198 per night from 1 Sept to 2 Sept
฿5,198
฿7,372 total
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (3,206 reviews)
Wonderfully Stay
"We thoroughly enjoyed our stay! The staff was friendly, so very helpful in what we asked, was just a wonderful experience!"

Reviewed on 5 Aug 2025

Hilton Boston Park Plaza
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.

Popular places to visit

Fenway Park which includes 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 showing 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 a skyscraper, landscape views and a park

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

The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

฿1,114
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
Narrated Sunset Cruise of Boston Harbor

Narrated Sunset Cruise of Boston Harbor

฿964
per adult
84% of travellers recommend
Narrated Sunset Cruise of Boston Harbor
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

฿2,751
per adult
76% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
See all activities in Brookline

Frequently asked questions

How much does a Brookline holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to Brookline costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Brookline?
You can generally find lower prices and greater availability in December, January and February. Explore our cheap Brookline holiday packages and you could score some excellent off-season deals.
How many days is enough for Brookline?
Brookline holidays come in many shapes and sizes, but to get a real feel for this place, we'd suggest 3 days is a good ballpark. In this timeframe, you can visit headline attractions like Coolidge Corner Theatre and Larz Anderson Park and seek out some underrated spots. Don't forget to explore cool areas such as South Boston and D Street - West Broadway either. If you plan wisely, you can even schedule a day trip or two from Brookline too.
Is it worth booking a holiday package to Brookline?
Brookline is a good holiday destination with attractions like Agganis Arena among the many things to keep you entertained. Whether you're heading away with the family or getting away with friends, a Brookline holiday promises fun for everyone.
How to find the best Brookline package deals?
Landing a cheap Brookline package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can personalise your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Brookline package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Brookline holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging accommodation and flights individually. Better still, you can tailor your Brookline trip to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Brookline?
If you're planning an impromptu Brookline adventure, browse 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 terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Brookline?

  1. Pick your dates: What you want to do in Brookline and your favourite season will help you decide when to travel.
  2. Set a budget: Factor in costs like flights, food and transportation when calculating how much to save for your trip to Brookline. Then, pick a hotel that suits your budget, whether that's an economical option or a swankier retreat.
  3. Decide your trip length: Consider how much time you want to spend discovering Brookline. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a personalised Brookline holiday package.

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