645+ Private Villas and Holiday Rentals in Chestnut Hill |
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Chestnut Hill Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Chestnut Hill

Discover more than 645 vacation rentals available in Chestnut Hill. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chestnut Hill.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chestnut Hill, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chestnut Hill. On average, places to stay near Chestnut Hill offer 581.09 ft², with nightly prices averaging ZA R5,987.

With Casai, finding and comparing holiday rentals in Chestnut Hill is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Chestnut Hill

Type Count
Holiday Apartments 381
Vacation Homes 171

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

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal 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

Casai 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 holiday rentals in Chestnut Hill?

With numerous options available in Chestnut Hill, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chestnut Hill:

How many holiday rentals have private pools in Chestnut Hill?

Discover a selection of holiday rentals with private pools near Chestnut Hill with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Chestnut Hill are best for families?

If you're searching for a family-friendly holiday home in Chestnut Hill, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chestnut Hill:

How many Casai.co.za holiday rentals are available in Chestnut Hill?

As of 2025, Casai boasts over 645 properties listed in the Chestnut Hill area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai 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 Holiday Rentals

Recently Booked Holiday Rentals in Chestnut Hill