Brookline Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Din Kime

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 Conte Forum, 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 3.744.049 ₫ per night from 6 Jul to 7 Jul
3.744.049 ₫
5.057.752 ₫ total
6 Jul - 7 Jul
includes taxes & fees
8/10 Very Good! (3,142 reviews)
"Was looking for a place to stay during our Jays /Red Sox games that was walking distance to Fenway park plus close to the subway as we were flying into Logan International Airport. The Arcadian was perfect, green "C" line was right across from hotel. Walk was about 10/15 mins on beautiful Beacon ..."

Reviewed on 1 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 5.069.414 ₫ per night from 5 Jul to 6 Jul
5.069.414 ₫
6.968.616 ₫ total
5 Jul - 6 Jul
includes taxes & fees
9/10 Wonderful! (3,626 reviews)
"We really enjoyed our stay at the Omni. They were accommodating with everything, even allowing us to check-in hours earlier than expected. It is a bit of a walk to get to the waterfront but we didn’t mind! The rooftop pool and hot tub area were really nice with a bar right beside. The artist rooms ..."

Reviewed on 1 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 4.544.358 ₫ per night from 6 Jul to 7 Jul
4.544.358 ₫
5.291.905 ₫ total
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (1,336 reviews)
"Love the location!"

Reviewed on 1 Jul 2025

citizenM Boston Back Bay
See all 3,762 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.

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.

Popular places to visit

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

Fenway Park

4.5/5(61 reviews)

Catch an event at Fenway Park during your trip to Boston. Attend a baseball game in this walkable area.

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(102 reviews)

Take a campus tour or just explore the area around Harvard University, a top university in Boston. Amble around this vibrant area's riverfront or experience its acclaimed art galleries.

Harvard University
Copley Square

Copley Square

4/5(16 reviews)

You can learn about the local history of Boston during your trip to a well-known site such as Copley Square. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.

Copley Square