The best rentals from the top sites, all in one place

We believe finding a vacation rental in Chestnut Hill should be easy and not take hours of searching and scrolling. We’ve designed VacationRenter from the ground up to help travelers find the perfect rental faster and easier.

Where to stay in Chestnut Hill

Vacation rentals in Chestnut Hill

There are 5,133 vacation rentals near Chestnut Hill for all manner or mood of travel, availability of time off, and size of budget. So, if you are hoping for an affordable Chestnut Hill vacation, you can find 10% rentals under $49/night. Or if you are willing to splurge on a luxury vacation in Chestnut Hill, there are 513 between $270 and $5,500/night. Whether you are sleeping by yourself or with a significant other, or are travelling with a group of 65 there are short term home and apartment rentals in Chestnut Hill to fit your Massachusetts vacation needs. The most popular types of short-term rental homes in Chestnut Hill are private rooms, apartments and houses. Chestnut Hill has been a frequently searched travel destination this year and continues to grow in popularity. VacationRenter offers a wide selection of vacation rental availability from leading travel sites like VRBO (Vacation Rentals By Owner), Homeaway,, and many more. Search your travel dates to find available Chestnut Hill vacation homes for your trip.

Home-types in Chestnut Hill

Chestnut Hill has a variety of property types for you to consider when booking a trip. Here are the most popular property types in Chestnut Hill:
- Oceanfront5,133 vacation rentals
- Beach5,133 vacation rentals
- Private Room1,481 vacation rentals
- Condo1,302 vacation rentals
- Apartment1,302 vacation rentals
- House284 vacation rentals
- Hotel111 vacation rentals
- Bed & Breakfast24 vacation rentals

Points of interests in Chestnut Hill

Chestnut Hill has several popular points of interest for you to check out when visiting the area. Here are the most popular points of interest in Chestnut Hill:
- Fenway Park: 34,824 vacation rentals
- Brookline Recreation Department: 5,133 vacation rentals
- Longyear Museum: 5,133 vacation rentals
- Hammond Pond Reservation: 5,133 vacation rentals
- Houghton Garden: 5,133 vacation rentals
- MDC Park: 5,133 vacation rentals
- Metropolitan Waterworks Museum: 5,133 vacation rentals
- Soule Playground: 5,133 vacation rentals
- Chestnut Hill Reservation: 5,133 vacation rentals