645+ Rental Villas and Private Getaways in Chestnut Hill |
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Chestnut Hill Vacation Rentals & One Degree Stays Homes

About Chestnut Hill Vacation Rentals

There are more than 645 vacation rentals that are available in Chestnut Hill. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Chestnut Hill.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Chestnut Hill, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Chestnut Hill. Places to stay near Chestnut Hill are 581.09 ft² on average, with prices averaging US $347 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Chestnut Hill with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Chestnut Hill

Type Count
Holiday Apartments 381
Vacation Homes 171

Use these Quick Filters to Find a Vacation Rental in Chestnut Hill

★ Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chestnut Hill.

Weather in Chestnut Hill, MA

View the weather forecast for Chestnut Hill before booking your Chestnut Hill Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Chestnut Hill, MA

OneDegreeStays offers a large selection of top attractions around Chestnut Hill. Research things to do on your vacation before you visit Chestnut Hill.


Boston College
Alumni Stadium
McMullen Museum
Osher Clinical Center
Fenway Park
Boston University
Harvard University
TD Garden
Boston Common
Faneuil Hall Marketplace
Boston Convention and Exhibition Center
Gillette Stadium
New England Aquarium
Northeastern University
Boston Museum of Fine Arts
Copley Square
Harvard Square
Massachusetts General Hospital
Museum of Science
Hynes Convention Center

Other Places to Stay in Chestnut Hill, MA


Osher Clinical Center 1,022 Properties
Woodland Heath 814 Properties
Alumni Stadium 740 Properties
Boston College 738 Properties
McMullen Museum 704 Properties
South Brookline 501 Properties

Frequently Asked Questions About Chestnut Hill?

What are the top vacation rentals in Chestnut Hill?

There are a lot of options in Chestnut Hill. If you plan on staying in the Chestnut Hill area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chestnut Hill:

How many vacation rentals have private pools in Chestnut Hill?

There are 6 vacation rentals with private pools near Chestnut Hill. Top-rated ODS homes that have access to a swimming pool include:

Which vacation homes in Chestnut Hill are best for families?

If you are looking for a family-friendly vacation home in Chestnut Hill, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chestnut Hill:

How many onedegreestays vacation rentals are available in Chestnut Hill?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 645 in the Chestnut Hill area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Chestnut Hill. 

Nearby Neighborhood (8) 
Neighborhood Property Count
Brighton Vacation Rentals in Boston, Massachusetts 87
Cleveland Circle Vacation Rentals in Boston, Massachusetts 71
Commonwealth Vacation Rentals in Boston, Massachusetts 28
Newton Corner Vacation Rentals in Boston, Massachusetts 497
Brook Farm Vacation Rentals in Boston, Massachusetts 176
Woodland Heath Vacation Rentals in Boston, Massachusetts 814
Thompsonville Vacation Rentals in Boston, Massachusetts 358
South Brookline Vacation Rentals in Boston, Massachusetts 501

People Also Ask

There are 645 Chestnut Hill, MA Vacation Rentals

Recently Booked Vacation Rentals in Chestnut Hill