Chestnut Hill Vacations from $349

Things to do near Chestnut Hill

Chestnut Hill, Brookline, Massachusetts, is a fantastic destination for city-themed, cultural, and family vacations. Visitors can enjoy outdoor adventures, friendly hikes, and explore beautiful parks, making it perfect for family travel. Additionally, the area features educational attractions and a vibrant shopping mall center, ensuring plenty of activities for everyone to enjoy. Whether you're looking for popular attractions or a relaxing day outdoors, Chestnut Hill has something to offer for every traveler.

Shopping

For a delightful shopping experience, visit Harvard Square, just 4 miles from Chestnut Hill, offering vibrant city vibes. Also, explore GASP, a unique store 2 miles away, or head to Copley Place, 5 miles away, where you'll find a mix of entertainment and family-friendly options.

Recreation

Experience vibrant entertainment at MGM Music Hall at Fenway, just 4 miles away, where live concerts elevate your spirit. For an energetic atmosphere, visit Agganis Arena, 3 miles away, showcasing thrilling sports events. Enjoy culture and romance at Coolidge Corner Theatre, also 3 miles away, with captivating films and performances.

Adventure

At LEGOLAND® Discovery Center, experience a fun-filled arcadeAdventureZone perfect for families, located 7 miles away. Enjoy the scenic trails of Minuteman Bikeway, a hikingTrail 5 miles away, or embrace the thrill of water sports at Courageous Sailing Center, also 7 miles away.

Nightlife

In Chestnut Hill, enjoy vibrant nightlife at nearby venues like Cambridge Common, a lively pub with a romantic atmosphere, located 5 miles away. For a unique experience, head to Park-9 Dog Bar, an 8-mile journey, where you can unwind with friends and furry companions in a fun setting.

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

Find the best attractions near Chestnut Hill

Chestnut Hill, Massachusetts, is a fantastic destination for culture enthusiasts and families alike, offering a blend of historic colleges, urban parks, and modern universities. Visitors can explore top attractions like the Chestnut Hill Reservoir, which provides stunning panoramic views, along with various other local sites that highlight the area's rich history and vibrant community. Whether you're seeking culture or family experiences, Chestnut Hill has something special for everyone.

• Fenway Park: Experience the excitement of America's pastime at this iconic baseball stadium. Known for its vibrant atmosphere, Fenway Park offers a unique blend of sports and culture, making it a must-visit for any sports enthusiast.
• Harvard University: Explore the historic grounds of the oldest institution of higher learning in the U.S. Harvard University showcases stunning architecture and rich cultural heritage, perfect for those interested in academia and history.
• Boston Common: Enjoy a leisurely day in the oldest public park in the U.S. Boston Common is ideal for families and outdoor lovers, featuring beautiful landscapes, walking paths, and a lively urban vibe.

Best time to go to Chestnut Hill

The best time to visit Chestnut Hill can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chestnut Hill falls in July, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Chestnut Hill falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	28.6°F (-1.9°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	29.8°F (-1.2°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	36.9°F (2.7°C)	Light Rain	Mostly Sunny	Slightly High	Average
April	47.8°F (8.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	58.5°F (14.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	66.6°F (19.2°C)	Light Rain	Mostly Sunny	Average	Average
July	73.6°F (23.1°C)	Light Rain	Mostly Sunny	Average	Average
August	72.3°F (22.4°C)	Light Rain	Mostly Sunny	Average	Average
September	65.3°F (18.5°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
October	54.7°F (12.6°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly High
November	43.3°F (6.3°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	34.9°F (1.6°C)	Light Rain	Mostly Sunny	Average	Slightly Low

Tips to save on your trip to Chestnut Hill

• Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
• Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Chestnut Hill.
• 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.