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 3,369 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 $45/night. Or if you are willing to splurge on a luxury vacation in Chestnut Hill, there are 337 between $298 and $10,000/night. Whether you are sleeping by yourself or with a significant other, or are travelling with a group of 400 there are short term home and apartment rentals in Chestnut Hill to fit your vacation needs. The most popular types of short-term rental homes in Chestnut Hill are condos, private rooms 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:
- Condo1,383 vacation rentals
- Private Room1,354 vacation rentals
- House361 vacation rentals
- Hotel118 vacation rentals
- Bed and Breakfast29 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:
- Durant-Kenrick House and Grounds: 5,133 vacation rentals
- Longyear Museum: 5,133 vacation rentals
- Houghton Garden: 5,133 vacation rentals
- Brookline Recreation Department: 5,133 vacation rentals
- Brighton Common: 5,133 vacation rentals
- Webster Conservation Area: 5,133 vacation rentals
- Chestnut Hill Reservation: 5,133 vacation rentals
- Hammond Pond Reservation: 5,133 vacation rentals
- Burr Playground: 5,133 vacation rentals
- Skyline Park: 5,133 vacation rentals