Destination guide

Take in the lush beauty of Chestnut Hill

The forests and surrounding scenery provide a peaceful ambience to your holiday 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-see attractions in the area. If you need more space to accommodate a family holiday or a trip with friends, 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 holiday 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 centre:

  • 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 centre:

  • 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)
How to get there

Transport to and around Chestnut Hill

Fly into Boston, MA (BOS-Logan Intl.), the closest airport, located 8.1 mi (13 km) from the city centre. 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.

How many holiday rentals are available around Chestnut Hill?

Our 2020 accommodation listings offer a large selection of 635 holiday lettings around Chestnut Hill. From 77 houses to 486 flats & apartments, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

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

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Chestnut Hill:

  • South End: 291 holiday homes
  • Jeffries Point: 22 holiday homes
  • Chinatown: 171 holiday homes
  • Dorchester: 372 holiday homes
  • Commonwealth: 56 holiday homes

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

What are the most popular points of interest and landmarks to stay near when travelling to Chestnut Hill? offers a large selection of holiday accommodations near great places in Chestnut Hill. From travellers, the most popular points of interest to stay near are:

  • Alumni Stadium: 823 holiday lettings
  • Chestnut Hill Station: 813 holiday lettings
  • Boston College: 827 holiday lettings
  • Salem Pioneer Village 1630: 1,025 holiday lettings
  • Quincy Market: 825 holiday lettings

But there are many other points of interest around Chestnut Hill listed on where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent Houses in Chestnut Hill?

Yes, of course. offers 77 Houses in Chestnut Hill. Our other popular types of Chestnut Hill holiday rentals include:

  • Flats: 486 self catering accommodations
  • Studios: 454 self catering accommodations
  • Townhouses: 12 self catering accommodations

But you can also enjoy a great stay in one of our other holiday rentals including Bed & breakfasts and more.

Can I find a holiday accommodation with pool in Chestnut Hill?

Yes, you can select your preferred holiday accommodation with pool among our 20 holiday homes with pool available in Chestnut Hill. Please use our search bar to access the selection of holiday rentals available.

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