Brookline Holidays

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Our guide on 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

Brookline Holiday

Our pick of the best Brookline Hotel Deals

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 NZ$336 per night from 29 July to 30 July
NZ$336
29 July - 30 July
includes taxes & fees
8/10 Very Good! (3,160 reviews)
"Nice quiet property in the middle of Brookline. Easy access to the MBTA Green line C branch to Cleveland Circle and Government Center Stations. Near I90 and down the street from Fenway Park"

Reviewed on 6 Jul. 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 NZ$532 per night from 7 Aug to 8 Aug
NZ$532
7 Aug - 8 Aug
includes taxes & fees
9/10 Wonderful! (3,638 reviews)
"The hotel itself looks grand. The location is nice and quiet. The room was super clean and met all basic needs. The pool was nice but dominated by kids. Anyways it was still nice to chill out by the pool. From minuses, the room was missing a coffee maker. And I was unpleasantly surprised by $35 per ..."

Reviewed on 6 Jul. 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 NZ$357 per night from 13 July to 14 July
NZ$357
13 July - 14 July
includes taxes & fees
9.2/10 Wonderful! (1,390 reviews)
"Very clean and progressive."

Reviewed on 8 Jul. 2025

citizenM Boston Back Bay
See all 3,790 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.

Discover the most popular places to visit in Brookline

Fenway Park which includes night scenes and a sporting event as well as a large group of people

Fenway Park

4.5/5(9 reviews)

The iconic home of the Boston Red Sox is on the must-see list of every red-blooded baseball fan.

Fenway Park
Harvard University which includes heritage architecture and a city

Harvard University

4.5/5(27 reviews)

You don’t have to be a history student to appreciate the unique heritage of this world-renowned academic institution.

Harvard University
Gillette Stadium

Gillette Stadium

Catch an event at Gillette Stadium during your trip to Foxboro. Experience the area's great live music and acclaimed theatre scene.

Gillette Stadium

What to do in Brookline

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

NZ$132
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

NZ$91
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

NZ$57
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 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.