Brookline Vacations from $319

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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 Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $637, price is now $319 per person
$319
per person
Nov 1 - Nov 3
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,333, price is now $786 per person
$786
per person
Nov 3 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Great location. Beautiful building and setting. Staff are helpful and friendly!

Reviewed on Aug 24, 2025

DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Save 100% on your flight
Price was $882, price is now $569 per person
$569
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8/10 Very Good! (2,072 reviews)
Good value for the price and our family of 5. I would prefer rooms with no carpet. It was fine, but questionable as I smelled chorine. Overall, it was fine. The front desk was helpful and the service was very good.

Reviewed on Aug 21, 2025

Fairfield Inn & Suites by Marriott Plymouth

Fairfield Inn & Suites by Marriott Plymouth

2.5 out of 5
Save 100% on your flight
Price was $603, price is now $390 per person
$390
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
8.8/10 Excellent! (474 reviews)
Clean and comfortable. Very easy to park.

Reviewed on Aug 5, 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
Price was $2,029, price is now $1,328 per person
$1,328
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.8/10 Excellent! (1,040 reviews)
A classic hotel - well situated- everything was very relaxed . They could benefit from having another bar or sports bar

Reviewed on Aug 25, 2025

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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

Discover the most popular places to visit in Brookline

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

Fenway Park

4.5/5(2,499 reviews)

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

4.5/5(1,966 reviews)

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 featuring landscape views, a skyscraper and flowers

Boston Common

4.5/5(4,786 reviews)

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

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$79
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

$70
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
Immersive American Revolution Self-Guided Walking & Driving Tours

Liberty, Freedom, and Revolution: American History Tours Bundle

$30
per traveler
Liberty, Freedom, and Revolution: American History Tours Bundle
See all activities in Brookline

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
$189 nightly
The price is $211 total per night from Sep 1 to Sep 2
$211 total
Sep 1 - Sep 2
Total with taxes and fees
8/10 Very Good! (3,374 reviews)
"Easy and early check in. Safe parking and much cheaper than most Boston hotels."

Reviewed on Aug 25, 2025

The Arcadian Hotel
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
$158 nightly
The price is $183 total per night from Sep 1 to Sep 2
$183 total
Sep 1 - Sep 2
Total with taxes and fees
9.6/10 Exceptional! (3,273 reviews)
"Our second stay at the Seaport Hotel and everything was amazing. We will continue to use this hotel for all of our Boston visits."

Reviewed on Aug 24, 2025

Seaport Hotel Boston
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
$239 nightly
The price is $278 total per night from Sep 1 to Sep 2
$278 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (3,868 reviews)
"Great hotel, nice staff, cool area"

Reviewed on Aug 25, 2025

Omni Boston Hotel at the Seaport
See all 3,805 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.

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Frequently asked questions

How much does a Brookline vacation package cost?
Offering great value package deals from $319 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

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.