Coolidge Corner South Side blends residential charm with cultural richness. Tree-lined streets and historic homes create a peaceful escape from Boston's urban energy. The area's strong Jewish community adds authentic character through kosher delis and local synagogues. Students from nearby Boston University bring youthful energy to area cafes and bookshops. The Green Line connects you easily to Boston attractions. Fenway Park, Harvard Square, and Copley Square are all within easy reach.
Washington Square in Brookline balances quiet charm with city access. Tree-lined streets showcase historic homes and early 20th-century architecture. Several synagogues reflect the area's Jewish heritage, while local boutiques and cafes create a welcoming area feel. The Green Line C branch makes exploring Boston a breeze. Diverse restaurants serve Mediterranean, Asian, and American cuisine at reasonable prices. Fenway Park and Harvard Square are just a short train ride away from this authentic residential haven.
North Brookline offers tree-lined streets where historic charm meets cultural diversity. The quiet area showcases beautiful early 20th-century architecture and well-maintained gardens. Visitors can explore the iconic Coolidge Corner Theatre and JFK's birthplace. The area provides a peaceful retreat from Boston's bustle. Excellent public transit connects you to city centre Boston in just 15-20 minutes. Diverse dining options include kosher delis, Asian restaurants, and upscale bistros. Small local shops and boutiques line Beacon Street while nearby Brookline Reservoir offers scenic walking paths for outdoor enthusiasts.
While Chestnut Hill may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Chestnut Hill Reservoir and Alumni Stadium.
Appreciated for its coffee shops and architecture, you might consider exploring Longwood. Check out the variety of things to see and do like Brookline Arts Center, and jump on the metro at Longwood Station or Hawes St. Station to get around the city.
Discover the most popular places to visit in Brookline
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.
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.
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 acclaimed art galleries or attend a sporting event in this vibrant area.
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.
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.
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 theatre scene in this vibrant area.
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.
WBUR CitySpace
You can make plans for a show at WBUR CitySpace on your trip to Brookline.
"Hi we've contacted you several times by message and phone but you've not given us the courtesy of a response. Hoping that you read your reviews and decide to come back to us."
"Breakfast was good, room was OK. Overall, the house gave a good vibe of an old Victorian style house. Even though everything inside is quite outdated. But it’s way overpriced for what you’re getting. Parking was quite a mess. For additional $18 you get a spot. But it’s a narrow side driveway so cars end up blocking each other. The staff did a great job helping with this. But… I didn’t expect to deal with it considering the cost. It would be an excellent option to stay if priced right in my...
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.
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.
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?
Pick your dates: What you want to do in Brookline and your favourite season will help you decide when to travel.
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.
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.
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.