Brookline Holidays

Photo by Ed Gaffny

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Top Flight + Hotel Deals in Brookline

Price found within the past 48 hours. Click for updated prices.
Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Save 100% on your flight
Price was €1,655, price is now €1,108 per person
€1,108
per person
8 Oct - 12 Oct
found 1 hour ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (1,108 reviews)
Very cool property. Checkin was smooth and room was as expected.

Reviewed on 21 Aug 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was €2,798, price is now €1,518 per person
€1,518
per person
8 Oct - 12 Oct
found 1 hour ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
One of the nicest overall properties in the country

Reviewed on 20 Aug 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was €2,442, price is now €1,475 per person
€1,475
per person
8 Oct - 12 Oct
found 1 hour ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
The Reffles Hotel is a fabulous place to stay. Hotel is amazing with a wonderful friendly staff.

Reviewed on 20 Aug 2025

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Save 100% on your flight
Price was €1,680, price is now €1,138 per person
€1,138
per person
8 Oct - 12 Oct
found 1 hour ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,055 reviews)
Great location and staff! I would definitely stay again!!

Reviewed on 20 Aug 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was €2,173, price is now €1,494 per person
€1,494
per person
8 Oct - 12 Oct
found 1 hour ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (433 reviews)
Beautiful building, friendly staff, great atmosphere

Reviewed on 16 Aug 2025

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 €173 per night from 1 Sept to 2 Sept
€173
1 Sept - 2 Sept
includes taxes & fees
8/10 Very Good! (3,351 reviews)
","

Reviewed on 18 Aug 2025

The Arcadian Hotel
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is €174 per night from 24 Aug to 25 Aug
€174
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (3,689 reviews)
Hands down AMAZING
"Our stay was amazing from start to finish! The check in staff was super helpful. Our room was ready earlier than expected which was great after travel. The hotel was close to everything, great food, great shopping and of course right beside TD Garden. The best part was the view from our room. Get ..."

Reviewed on 20 Aug 2025

citizenM Boston North Station
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is €167 per night from 1 Sept to 2 Sept
€167
1 Sept - 2 Sept
includes taxes & fees
9.6/10 Exceptional! (3,260 reviews)
"Wonderful area!"

Reviewed on 20 Aug 2025

Seaport Hotel Boston
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.

Popular places to visit

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

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
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

What to do in Brookline

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

€68
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

€61
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

€29
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 from €1,108 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.