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Best Vacation Homes in Chestnut Hill

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Chestnut Hill Luxury Rentals

10.0 (2 Reviews)
House
Gorgeous 5 bed Historic Boston Home
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
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Chestnut Hill Pet Friendly Vacation Rentals

3.6 (4 Reviews)
Apartment
182 Heath st
  • Pet Friendly
  • Child Friendly
  • Internet
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Chestnut Hill Large Vacation Homes

9.3 (91 Reviews)
Bed & Breakfast
Natalie House
  • Air Conditioner
  • Parking
  • TV
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Why Choose Rent By Owner for your Chestnut Hill Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Chestnut Hill Vacation Rentals

Where are the best neighborhoods to stay in Chestnut Hill?

When choosing where to stay in Chestnut Hill, Massachusetts, you’ll find a variety of charming neighborhoods that offer both convenience and character. This area’s residential communities provide a peaceful retreat while remaining close to the vibrant local amenities and cultural attractions. Whether you prefer a quiet street with tree-lined sidewalks or a lively neighborhood with easy access to outdoor spaces, there are plenty of options to suit your travel style. By selecting a well-situated vacation rental in Chestnut Hill, you can enjoy an authentic experience in this welcoming Massachusetts community, making your visit both comfortable and memorable.

Brighton

Located just outside the heart of Boston, this neighborhood offers easy access to vibrant city life while providing a more relaxed atmosphere for your stay. It’s ideal for travelers seeking convenient transit options and diverse dining experiences.

View 87+ Rentals in Brighton

Cleveland Circle

This area is well-known for its lively community vibe and access to public transportation, making it a great base for exploring the region. Here, you can enjoy a balance of urban convenience and local charm during your visit.

View 71+ Rentals in Cleveland Circle

Woodland Heath

Nestled within the scenic landscape of Chestnut Hill, Woodland Heath provides a tranquil setting perfect for relaxation. It’s an excellent choice for those looking to experience the area's natural beauty while staying close to amenities.

View 814+ Rentals in Woodland Heath

Thompsonville

This quiet neighborhood in Newton offers a welcoming environment with easy access to shopping and local parks. It’s suited for visitors who prefer a peaceful retreat within reach of the region's attractions.

View 358+ Rentals in Thompsonville

South Brookline

Known for its historic charm and lush surroundings, South Brookline provides a sophisticated backdrop for your stay. It’s perfect for travelers wanting to explore the area's cultural sites and scenic streets.

View 501+ Rentals in South Brookline

Commonwealth

This central neighborhood offers proximity to major attractions and downtown conveniences, making it an ideal location for exploring the region. Its vibrant community atmosphere enhances your regional experience.

View 28+ Rentals in Commonwealth

Brook Farm

A historically significant area with a charming residential feel, Brook Farm is perfect for those interested in experiencing local history and enjoying peaceful surroundings. It provides easy access to the region's various amenities.

View 176+ Rentals in Brook Farm

Newton Corner

Situated at the gateway to the region, Newton Corner combines suburban tranquility with convenient transit links. It’s suitable for travelers aiming to stay near both natural parks and city attractions.

View 497+ Rentals in Newton Corner

Best Times to Visit Chestnut Hill

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here ensures you can enjoy the region's natural beauty and local charm at its best, making your stay in this destination truly memorable.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, the area experiences pleasant weather, making it ideal for exploring local attractions and enjoying outdoor activities.

Average Temperature Daytime: around 75°F to 80°F - Nighttime: around 55°F to 60°F
autumn
Fall (September to October)

This is the most vibrant time to visit, with colorful foliage that enhances the scenic beauty of the region, perfect for outdoor enthusiasts and photography lovers.

Average Temperature Daytime: around 70°F to 75°F - Nighttime: around 50°F to 55°F

Off-Season Highlights

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Winter (December to February)

The quiet winter months offer a peaceful atmosphere, with cooler temperatures ideal for cozy stays indoors or winter sports in nearby areas.

Average Temperature Daytime: around 30°F to 40°F - Nighttime: around 20°F to 25°F
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Late Fall and Early Spring (November and March)

During these shoulder seasons, you’ll find fewer crowds and more affordable rates, with mild weather making it suitable for a relaxed visit.

Average Temperature Daytime: around 45°F to 55°F - Nighttime: around 35°F to 40°F

Weekly Weather Forecast for Chestnut Hill

How to Book Your Chestnut Hill Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Chestnut Hill

More Top-Rated Vacation Rentals in Chestnut Hill Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor patio or deck for relaxing or dining al fresco amidst the scenic surroundings.
  • Take advantage of well-maintained gardens and landscaped yards that enhance your outdoor experience.
  • Make use of a spacious backyard ideal for outdoor activities or social gatherings.
  • Benefit from easy access to nearby walking trails or nature paths for exploring the area's natural beauty.
  • Utilize outdoor furniture and loungers to unwind and soak up the regional sunshine.
  • Experience outdoor grilling facilities to enjoy cookouts with friends and family in this destination.
  • Access to parking areas that accommodate outdoor gear or vehicles during your stay in this region.

Top Attractions Around Chestnut Hill

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities and cultural experiences that make your stay memorable and enriching.

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Family Activities

  • Brookline Avenue Greenway: Explore this family-friendly outdoor space in the area, perfect for biking, walking, and enjoying picnics amidst scenic views.
  • Boston College Campus Tour: Discover the historic and picturesque campus, offering engaging guided tours that are ideal for curious children and history enthusiasts alike.
  • The Chestnut Hill Reservoir: Enjoy a leisurely walk or a relaxing day by the water at this popular local spot, which is great for family outings and nature exploration.
  • Henry Wagner Memorial Park: Spend quality time outdoors at this nearby park, providing playgrounds, open fields, and peaceful green spaces for family fun.
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Adult Activities

  • Visit the Boston College Campus: Explore the historic grounds and beautiful architecture of one of the region’s most renowned universities.
  • Enjoy a Day at the Chestnut Hill Reservoir: Take a leisurely walk or jog around the scenic reservoir, perfect for outdoor relaxation and sightseeing in this charming area.
  • Shop and Dine at the Chestnut Hill Square: Experience a variety of shopping, dining, and entertainment options just moments from your vacation rental in the region.
  • Explore the Arnold Arboretum: Discover an impressive collection of trees and plant life at this expansive botanical garden, ideal for nature enthusiasts visiting here.

Other Places to Stay in Chestnut Hill, MA

Osher Clinical Center
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Woodland Heath
Woodland Heath Vacation Rentals
Alumni Stadium
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Boston College
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McMullen Museum
McMullen Museum Vacation Rentals
South Brookline
South Brookline Vacation Rentals
More Places to Stay Near Chestnut Hill

Chestnut Hill Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining options: Take advantage of the area's diverse restaurants to enjoy authentic regional flavors during your stay.
  • Visit nearby cultural spots: Immerse yourself in the region's history and arts by exploring nearby galleries and historic sites.
  • Plan outdoor activities: Use this destination’s scenic parks and walking trails to make the most of the natural beauty here.
  • Discover convenient transportation: Determine the best local transit options or arranging for a vehicle to effortlessly explore all that the area has to offer.

Transportation Options

  • MBTA Green Line Trolley: You can conveniently access the region’s public transit system via the Green Line, connecting you directly to Boston and other key areas.
  • Commuter Rail Services: Commuter trains offer a reliable option for traveling between here and downtown Boston, ideal for daily commutes or exploring the city.
  • Bus Routes: Local bus services provide flexible transportation options around the area, making it easy to reach nearby neighborhoods and attractions.
  • Taxis and Rideshare Services: Taxis and modern rideshare options like Uber and Lyft are readily available for quick, door-to-door travel within the region.

Local Customs Options

  • Local Coffeehouse Culture: Embrace the area's vibrant coffee scene by visiting cozy cafes that reflect the community's friendly and welcoming spirit.
  • Historical Preservation: Appreciate the region’s dedication to maintaining its historic architecture, offering a glimpse into the area's rich past through well-preserved buildings and landmarks.
  • Community Events: Participate in seasonal festivals and outdoor gatherings that highlight the area's strong sense of community and local pride.
  • Dining Etiquette: Respect the local customs of casual yet courteous dining, often characterized by farm-to-table eateries that celebrate regional flavors.

Frequently Asked Questions About Chestnut Hill?

1. 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:

2. How many vacation rentals have private pools in Chestnut Hill?

There are 9 vacation rentals with private pools near Chestnut Hill. Top-rated RBO homes that have access to a swimming pool include:

3. 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:

4. How many Rentbyowner vacation rentals are available in Chestnut Hill?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 643 in the Chestnut Hill area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chestnut Hill. 

5. What is the cancellation policy for vacation rentals in Chestnut Hill, Massachusetts?

Cancellation policies vary by individual property listing. You should review the specific terms on the listing page or contact the property owner directly to understand the cancellation window and any applicable fees.

6. How do I know if a vacation rental in Chestnut Hill is available for my travel dates?

Availability is displayed on each listing's calendar. If you have questions about open dates or need flexible booking options, reach out to the property owner for further assistance.

7. Are there any specific amenities I should expect in a vacation rental here?

Amenities differ among properties, so check the detailed listing description for information on features like Wi-Fi, parking, kitchens, or outdoor spaces. For special requests, contacting the owner helps ensure your needs are met.

8. What is the process for securing a reservation in this area?

Reservations are made through the booking platform, which guides you through selecting dates, confirming availability, and completing your payment. Confirming details with the property owner can also provide additional assurance.

9. Is it safe to book a vacation rental here, and what measures are in place?

The platform ensures secure transactions and verified listings. To maximize safety, always review the property’s reviews and communicate directly with the owner before finalizing your reservation.