Brookline Trips (flight + hotel)

Photo by Ed Gaffny

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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

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 P8,597 per night from Jul 30 to Jul 31
P8,597
P11,517 total
Jul 30 - Jul 31
includes taxes & fees
8/10 Very Good! (3,243 reviews)
"I stay here every time i’m in boston"

Reviewed on Jul 24, 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 P10,466 per night from Aug 24 to Aug 25
P10,466
P14,517 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (3,719 reviews)
"Great location and excellent common spaces"

Reviewed on Jul 25, 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 P10,798 per night from Aug 10 to Aug 11
P10,798
P12,574 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (1,493 reviews)
"Very nice hotel but rooms are very small. Bathroom in the room provides almost no privacy from the rest of the room and is extremely small. The sink isn’t even in the bathroom. The bed is very comfortable but is only accessible from one side. This is definitely a hotel for the gen z crowd. If you ..."

Reviewed on Jul 26, 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.

Popular places to visit

Harvard University which includes heritage architecture and a city

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
New England Aquarium

New England Aquarium

From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips.

New England Aquarium
Massachusetts showing outdoor eating, a house and cafe lifestyle

Newbury Street

Stretching between Massachusetts Avenue and Boston Public Gardens, this upscale street is one of Boston’s most popular shopping and dining destinations.

Newbury Street

What to do in Brookline

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

P4,479
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

P3,978
per adult
86% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

P1,916
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?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation 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 vacation packages and you could score some excellent off-season deals.
How many days is enough for Brookline?
Brookline vacations 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 vacation package to Brookline?
Brookline is a good vacation 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 vacation 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 personalize 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 vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging accommodations 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 vacation 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 favorite 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 personalized Brookline vacation package.

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