Destination guide

Take in the lush beauty of Chestnut Hill

The forests and surrounding scenery provide a peaceful ambiance to your vacation home in Chestnut Hill. Renowned for its university setting, football games and bird watching, this city welcomes all visitors. Boston Museum of Fine Arts and Fenway Park are just a couple of the must-sees in the area. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.


Sightseeing in and around Chestnut Hill

Are you searching for attractions to visit during your stay? Venture out of your vacation home and experience everything that Chestnut Hill has to offer. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • New England Aquarium (6.4 mi / 10.3 km)
  • Franklin Park Zoo (4.1 mi / 6.5 km)
  • Artisans Asylum (5.3 mi / 8.5 km)
  • Blue Hills Ski Area (7.7 mi / 12.3 km)
  • F1 Boston (9.3 mi / 15 km)
  • Fun and Games Family Entertainment Center (12 mi / 19.3 km)
Natural features

Exploring the natural landscape of Chestnut Hill

Whether you're an outdoor enthusiast or just want to take in the scenery, Chestnut Hill is a great spot to appreciate mother nature. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Boston Public Garden (5.4 mi / 8.7 km)
  • Boston Common (5.6 mi / 9 km)
  • Walden Pond (12.5 mi / 20.1 km)
  • Arnold Arboretum (2.4 mi / 3.9 km)
  • Back Bay Fens (4 mi / 6.4 km)
  • Charles River Esplanade (5.3 mi / 8.5 km)

Transportation to and around Chestnut Hill

Fly into Boston, MA (BOS-Logan Intl.), the closest airport, located 8.1 mi (13 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Norwood, MA (OWD-Norwood Memorial), which is 9.1 mi (14.7 km) away.

You might consider catching a ride on the metro at Chestnut Hill Station for ease of access to the rest of the city.

Where to stay around Chestnut Hill?

Our 2019 property listings offer a large selection of 1,396 vacation rentals near Chestnut Hill. From 160 Houses to 987 Studios, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chestnut Hill for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Chestnut Hill?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Chestnut Hill:

  • Back Bay: 661 vacation rentals
  • North End: 384 vacation rentals
  • Beacon Hill: 490 vacation rentals
  • Downtown: 666 vacation rentals
  • Jamaica Plain: 62 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

Can I rent Houses in Chestnut Hill?

Yes, of course. HomeAway has 160 Houses in Chestnut Hill. Our other popular types of vacation rentals in Chestnut Hill include:

  • Studios: 987 rentals available
  • Boats: 9 rentals available
  • Condos/Apartments: 1,129 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Villas and more.

Can I find a vacation rental with pool in Chestnut Hill?

Yes, you can select your preferred vacation rental with pool among our 57 vacation rentals with pool available in Chestnut Hill. Please use our search bar to access the selection of vacation rentals available.