Brookline Holidays

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Top Flight + Hotel Deals in Brookline

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

Iris Hotel Boston

Coolidge Corner
€1,191
per person
8 Oct - 15 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (656 reviews)
Boston Harbor Hotel

Boston Harbor Hotel

North End
€2,134
per person
23 Oct - 29 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,011 reviews)
A bit dated, but beautiful situated and appointed. Little ways from everything.

Reviewed on 28 Aug 2026

The Newbury Boston

The Newbury Boston

Back Bay
€2,645
per person
8 Oct - 15 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (709 reviews)
Raffles Boston

Raffles Boston

Back Bay
€2,958
per person
23 Oct - 29 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (305 reviews)
Eurostars The Boxer

Eurostars The Boxer

West End
€1,436
per person
23 Oct - 29 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
8.8/10 Excellent! (1,566 reviews)

Things to do in and around Brookline

Brookline offers a delightful blend of culture and urban charm, ideal for tourists seeking educational experiences, music concerts, and shopping at local centres. Visitors can enjoy a variety of activities, including day trips, upcoming tours, and sporting events, ensuring a memorable stay. Don't miss the opportunity to explore the vibrant local scene that captures the essence of this charming Massachusetts town.

Shopping

In Brookline, you can explore GASP for unique gifts. Nearby, Harvard Square offers a vibrant shopping experience with a mix of shops and entertainment, just 4.8km away. If you're up for a drive, Bow Market, located 6.4km away, features charming stalls in a lively atmosphere.

Recreation

In Brookline, the Coolidge Corner Theatre offers a charming atmosphere for film enthusiasts, blending romance and culture. For sports fans, Agganis Arena provides an energetic vibe just 1.6km away, while the House of Blues Boston, located two miles from Brookline, delivers vibrant live music experiences.

Adventure

LEGOLAND® Discovery Center, located 8.0km from Brookline, offers a vibrant arcade adventure for families, filled with interactive attractions. Sky Zone Boston Indoor Trampoline Park, situated 11.3km away, invites thrill-seekers to bounce and flip in an energetic environment. For a scenic hike, explore the Irish Heritage Trail, 6.4km from Brookline, showcasing beautiful outdoor landscapes.

Nightlife

Brookline's nightlife offers charming venues like Cambridge Common, a delightful pub with romantic vibes just 4.8km away, and Park-9 Dog Bar, located 9.7km away, where you can enjoy a lively atmosphere and entertainment while unwinding with friends over drinks.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Brookline

Brookline offers a delightful blend of cultural, urban, and business-themed attractions, making it an ideal destination for various travellers. Visitors can explore historic colleges and universities, enjoy the serene urban parks, and attend events at conference venues. With a range of points of interest catering to those seeking cultural experiences, family fun, and city life, Brookline promises a memorable visit for all.

  • Fenway Park: Experience the thrill of a Boston Red Sox game at Fenway Park, one of the oldest baseball stadiums in the USA. The atmosphere is electric, steeped in rich sporting history, and surrounded by vibrant local culture.
  • Harvard University: Stroll through the picturesque campus of Harvard University, the oldest institution of higher education in the United States. Its iconic architecture and rich academic heritage offer a unique glimpse into a world of learning and culture.
  • TD Garden: Attend an event at TD Garden, a premier venue for sports and entertainment. Hosting everything from NHL games to concerts, its modern facilities and dynamic atmosphere make it a central hub for Boston's business and leisure activities.

Best time to go to Brookline

The best time to visit Brookline is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.8°F (-1.8°C)Light RainMostly SunnyAverageSlightly Low
February30.0°F (-1.1°C)Light RainMostly SunnyAverageSlightly Low
March36.9°F (2.7°C)Light RainMostly SunnyAverageAverage
April47.8°F (8.8°C)Light RainMostly SunnySlightly HighAverage
May58.5°F (14.7°C)Light RainMostly SunnyAverageSlightly High
June66.6°F (19.2°C)Light RainMostly SunnyAverageAverage
July73.6°F (23.1°C)Light RainMostly SunnySlightly HighAverage
August72.5°F (22.5°C)Light RainMostly SunnyAverageAverage
September65.5°F (18.6°C)Light RainMostly SunnySlightly HighSlightly High
October54.9°F (12.7°C)Light RainMostly SunnySlightly LowSlightly High
November43.5°F (6.4°C)Light RainMostly SunnySlightly LowAverage
December35.1°F (1.7°C)Light RainMostly SunnySlightly LowSlightly Low

Tips to save on your trip to Brookline

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Brookline.
  • Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Brookline.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Top hotels in Brookline

Arcadian Hotel

Arcadian Hotel

1200 Beacon St Brookline MA
Fully refundableReserve now, pay when you stay
€211
7 Sept - 8 Sept
includes taxes & fees
8.2/10 Very good! (4,412 reviews)
"Very nice hotel as usual"

Reviewed on 28 Aug 2026

Arcadian Hotel
Iris Hotel Boston

Iris Hotel Boston

30 Webster St Brookline MA
Fully refundableReserve now, pay when you stay
€297
20 Sept - 21 Sept
includes taxes & fees
Iris Hotel Boston
Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
€218
20 Sept - 21 Sept
includes taxes & fees
Seaport Hotel Boston
See all 4,267 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.

Stay near popular Brookline attractions

A narrow alley with brick buildings, colorful outdoor seating, and a brightly lit sign.
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.
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A quiet residential street lined with two-story houses, a sidewalk, and lush greenery.

John Fitzgerald Kennedy National Historic Site

8.6/10 (24 reviews)
Step back in time at JFK's birthplace, where Rose Kennedy meticulously restored her son's childhood home. Guided tours reveal intimate family stories and the modest beginnings of America's 35th president.
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A gazebo, a fountain, and a pond in a park.

Larz Anderson Park

8.6/10 (17 reviews)
This historic 64-acre park offers panoramic Boston skyline views and houses America's oldest car collection. Explore the Larz Anderson Auto Museum, stroll Italian gardens, or enjoy seasonal activities.
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A red brick house with green shutters, surrounded by lush greenery and trees.

Frederick Law Olmsted National Historic Site

8.6/10 (15 reviews)
You can find out about the history of Brookline with a stop at Frederick Law Olmsted National Historic Site. Experience the fascinating museums or attend a sporting event in this vibrant area.
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Larz Anderson Auto Museum

8.2/10 (14 reviews)
America's oldest car collection resides in a historic 1888 carriage house at the Larz Anderson Auto Museum. Explore vintage cars while attending seasonal Lawn Events with themed classic car displays.
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Brookline Farmers Market

9.0/10 (30 reviews)
This vibrant market showcases New England vendors selling fresh produce and artisanal goods since 1977. Browse seasonal fruits, handcrafted cheeses, and freshly baked treats while connecting with local farmers.
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Photographic Resource Center

8.8/10 (6 reviews)
You can study the exhibits at Photographic Resource Center, a museum with a story of its own, during your holiday in Brookline. Experience the fascinating museums and acclaimed art galleries in this vibrant area.
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Brookline Arts Center

Enjoy an outing to Brookline Arts Center during your stay in Brookline.
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What to do in Brookline

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

€40
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
View Boston Observation Deck General Admission

View Boston Observation Deck General Admission

€29
per adult
View Boston Observation Deck General Admission
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

€61
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
See all activities in Brookline

Frequently asked questions

How much does a Brookline holiday package cost?
Offering great value package deals from €1,191 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.

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.