Where to stay around Chestnut Hill, MA?

Our 2019 property listings offer a large selection of 2,231 vacation rentals near Chestnut Hill. From 1,273 Condos/Apartments to 1,060 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 VRBO.

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:

  • North End: 453 vacation rentals
  • Back Bay: 1,046 vacation rentals
  • Beacon Hill: 571 vacation rentals
  • Charlestown: 74 vacation rentals
  • Dorchester: 1,511 vacation rentals

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

Can I rent Condos/Apartments in Chestnut Hill?

Yes, of course. VRBO has 1,273 Condos/Apartments in Chestnut Hill. Our other popular types of vacation rentals in Chestnut Hill include:

  • Studios: 1,060 rentals available
  • Hotels: 717 rentals available
  • Houses: 157 rentals available

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

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

Yes, you can select your prefered vacation rental with pool among our 460 vacation rentals with pool available in Chestnut Hill. Please use our search bar to access the selection of vacation rentals available.

    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)

    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)