Brookline Vacations from $706

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Your Brookline Vacation

Reserve a Brookline vacation package and prepare to experience the best of this lively city. Consider staying in the neighborhood of Downtown Boston, which is great for nightlife, shopping and bars and pubs. If a sightseeing tour is part of the plan during your trip to Brookline, look around major attractions like Fenway Park, Boston Common and Boston Museum of Fine Arts. Don't put off your visit to this destination any longer. The ultimate Brookline vacation is just a few clicks away with Expedia.

The Latest Brookline vacation packages

Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,128, price is now $706 per person
$706
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Great all around.

Reviewed on Jul 8, 2026

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $1,450, price is now $899 per person
$899
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.

Reviewed on May 19, 2026

Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Save 100% on your flight
Price was $1,588, price is now $1,039 per person
$1,039
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8/10 Very Good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Save 100% on your flight
Price was $1,332, price is now $887 per person
$887
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (177 reviews)
Lovely hotel!

Reviewed on Jul 6, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was $2,441, price is now $1,626 per person
$1,626
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

Don't see what you're looking for?
See all available trips from Columbus to Brookline
View all trips

Stay near popular Brookline attractions

A narrow alley with brick buildings, colorful outdoor seating, and a brightly lit sign.
Photo by Din Kime
Open Photo by Din Kime

Coolidge Corner Theatre

8.6/10 (38 reviews)
This Art Deco landmark showcases independent and international films in a historic setting. Enjoy curated screenings, special Q&A events, and the vibrant community atmosphere of New England's premier nonprofit cinema.
See properties

What to do in Brookline

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$84
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Tour of Historic Fenway Park, America's Most Beloved Ballpark

Tour of Historic Fenway Park, America's Most Beloved Ballpark

$45
per adult
98% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

$47
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
See all activities in Brookline

Brookline Hotel Deals

Arcadian Hotel

Arcadian Hotel

3.5 out of 5
1200 Beacon St Brookline MA
Fully refundableReserve now, pay when you stay
$236 nightly
The price is $264 total per night from Jul 14 to Jul 15
$264 total
Jul 14 - Jul 15
Total with taxes and fees
8/10 Very Good! (4,293 reviews)
"Breakfast is hit and miss. Mostly sweet bread and cereal. One day there was yogurt. The rooms themselves are a bit dark, even with all the lights on. The staff was great though."

Reviewed on Jul 7, 2026

Arcadian Hotel
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $195 total per night from Jul 26 to Jul 27
$195 total
Jul 26 - Jul 27
Total with taxes and fees
9/10 Wonderful! (2,425 reviews)
"The location was great and the staff were amazing. I enjoyed the free shuttle that takes you to local areas."

Reviewed on Jul 7, 2026

Hyatt Regency Boston/Cambridge
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$214 nightly
The price is $249 total per night from Jul 26 to Jul 27
$249 total
Jul 26 - Jul 27
Total with taxes and fees
9.6/10 Exceptional! (4,538 reviews)
"Lovely property in an amazing location!"

Reviewed on Jul 7, 2026

Seaport Hotel Boston
See all 4,254 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.

Find the Best Brookline Vacation Packages

Brookline Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
58,700
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
New England Aquarium, Boston Museum of Fine Arts and Revere Beach

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Brookline vacation package cost?
Offering great value package deals from $706 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're likely to find lower rates and greater availability in November, December and January. Take a look at our cheap Brookline vacation packages and you could score some great off-season deals.
How many days is enough for Brookline?
We suggest planning a Brookline vacation for at least 3 days. This will give you enough time to check off top sights such as Larz Anderson Park and Frederick Law Olmsted National Historic Site, and explore neighborhoods like Back Bay and Back Bay East. You might even be able to squeeze in one or two day trips beyond Brookline.
Is it worth booking a vacation package to Brookline?
Brookline has everything you need for an unforgettable trip. Begin your Brookline vacation on a high note by exploring popular attractions like Agganis Arena.
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: The things you'd like to do in Brookline and your preferred season will help you decide when to get away.
  2. Work out your budget: Make sure you have enough money to cover everything from meals and transportation to flights and experiences. Your hotel will probably be the largest expense during your trip to Brookline.
  3. Use our trip planning tool to explore Brookline: Research every part of your trip to Brookline with this comprehensive planner. Invite friends or family to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Determine how many days away: Start by making a list of all the sights and activities you want to get to in Brookline. Then, estimate how long you'll need at each, including any travel time.
  5. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to choose a Brookline vacation package that brings all your bookings together.
  6. Book any activities or day trips: Now to the fun part — locking in everything you want to do and see. Check out some of the best things to do in Brookline and book your tickets early to save time (and maybe some spending money too!).

Does Expedia offer Book Now, Pay Later Brookline vacation packages?
If you're anything like us, you love traveling but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Brookline trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you spot them.

Explore a world of travel with Expedia

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