Chestnut Hill holiday rentals

We found 11 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Chestnut Hill that are perfect for your trip. Holiday rentals provide the best amenities for your family, friends or furry companion, such as Wi-Fi and cable TV. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Can I find a holiday rental in Chestnut Hill?
Yes, we offer holiday rentals where you'll be just 5.9 mi (9.5 km) from New England Aquarium, providing a secluded option if you'd like a quiet spot to stay.
What can I see and do in Chestnut Hill?
While exploring the area, visit family-friendly sights like New England Aquarium, or get outside and enjoy nature at Boston Common. Other popular places to visit in the area include Fenway Park and Harvard Square.
What are holiday rentals like in Chestnut Hill?
Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chestnut Hill. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.