Photo by Ed Gaffny

Chestnut Hill vacation rentals

We found 1,743 vacation rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Scroll through and select from vacation rentals in Chestnut Hill to find one that's perfect for your trip. Whether you're going on vacation with family or friends, vacation rentals have the amenities you expect for your stay, which might include parking and a fireplace. You're sure to find a rental to meet everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

The lush setting of Chestnut Hill is ready to explore

The forests and other outdoor surroundings create an inviting atmosphere in Chestnut Hill. This city's university setting, football games and bird watching draw many visitors. Fenway Park and TD Garden are just a couple of the must-sees in the area. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Chestnut Hill

Do you want to find things to do while you're in the area? Venture out of your cozy vacation rental and check out everything that makes Chestnut Hill a fun spot to vacation. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • New England Aquarium (6.4 mi / 10.4 km)
  • Encore Boston Harbor (7.2 mi / 11.6 km)
  • Samuel Adams Brewery (3.1 mi / 5 km)
  • Franklin Park Zoo (3.9 mi / 6.2 km)
  • Boston Marathon Finish Line (4.8 mi / 7.7 km)
  • Harpoon Brewery (6.8 mi / 10.9 km)

Exploring the natural features in Chestnut Hill

Whether you're an active traveler or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Chestnut Hill. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Copley Square (4.9 mi / 7.9 km)
  • Boston Common (5.6 mi / 8.9 km)
  • Arnold Arboretum (2.4 mi / 3.9 km)
  • Back Bay Fens (4 mi / 6.5 km)
  • Commonwealth Avenue Mall (4.4 mi / 7.1 km)
  • Charles River Esplanade (5.3 mi / 8.6 km)

Traveling to and around Chestnut Hill

Fly into Boston, MA (BNH-Boston Harbor Seaplane Base), the closest airport, located 7.5 mi (12 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Logan International Airport (BOS), which is 8.1 mi (13 km) away.

You might consider catching a ride on the metro at Chestnut Hill Station for ease of access to the rest of the city.

Frequently asked questions

What is the best area to stay in Chestnut Hill when booking a vacation rental?

If you're planning a vacation in Chestnut Hill, South Brookline is one of the most in-demand locations to stay. Whatever your style of travel, Vrbo is bound to have a property here that matches your needs.

What is the most popular type of vacation rental accommodation in Chestnut Hill?

Based on our research, apartments are the most desirable type of vacation rental in Chestnut Hill. But naturally, everyone's idea of an awesome trip isn't going to be the same. Vrbo has vacation homes in a variety of sizes and shapes, and we'll help you find your ideal fit.

How much does it cost to rent a vacation rental in Chestnut Hill?

The average price for a vacation home in Chestnut Hill is determined by a number of factors, including time of year, length of stay and property type. Whether you're dreaming about a sprawling villa with space for extended family or a comfy cabin for just you and the kids, just enter your dates of travel to view stays with fantastic value.

How much does it cost to rent a beach house in Chestnut Hill?

The average price for a vacation rental close to the beach in Chestnut Hill depends on when you'll be there and the style and size of property you're looking for. You can find prices easily and quickly on Vrbo by entering the dates you'll be traveling. Then make use of the filter tool to choose the number of bedrooms and amenities important to you, such as WiFi, air conditioning and a hot tub.

Are there pet-friendly vacation rentals in Chestnut Hill?

You're in luck! There are. You'll have your pick of 13 vacation rentals that cater to pets in Chestnut Hill. Lots of our pet-friendly vacation rentals even come with an outdoor area for your four-legged friend to run around in, doggie beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find a pad that'll get tails wagging on Vrbo.

What are popular rental amenities in Chestnut Hill?

A fireplace, an electric car charging station and a firepit are rated the most popular rental amenities in Chestnut Hill. Whether you're taking to the road alone, with your sweetheart or a group of dear friends, Vrbo can help you find a vacation rental that matches your style with all the features you need.

Are there large group vacation rentals in Chestnut Hill?

Take your pick of three Vrbo properties in Chestnut Hill that can host five or more people. You'll get all the space and privacy you need to have fun with your nearest and dearest — and no one else.

Are there vacation rentals in Chestnut Hill that welcome kids?

Chestnut Hill has 13 family-friendly vacation rentals. And finding a stay that welcomes youngsters is easy with our "Properties good for families" filter. Besides having the whole place to yourselves, you'll also get access to conveniences and perks such as dining rooms, kitchens and private pools.

What are the top attractions for families in Chestnut Hill?

Keep the kids busy at these top family-friendly attractions in Chestnut Hill:

  • Larz Anderson Auto Museum
  • Larz Anderson Park
  • Coolidge Corner Theatre

Are there one-bedroom vacation rentals in Chestnut Hill?

Yes, Chestnut Hill has four one-bedroom rentals available. Typically located in prime areas because of their smaller size, a one-bedroom vacation property is ideal if you're traveling with a friend or your partner. And with home comforts such as full kitchens and more privacy than a standard hotel, you'll be able to chill out while sightseeing around this fabulous destination.

Can I find two-bedroom vacation rentals in Chestnut Hill?

Chestnut Hill has three two-bedroom vacation rentals for you to select from. Discover a vacation home with all the space and comfort you want at a price that's hard to resist on Vrbo.

Are there vacation rentals with WiFi in Chestnut Hill?

You can pick from four vacation rentals with WiFi in Chestnut Hill. If you want to disconnect from daily life while on vacation, but still need to be connected to the web, these getaways are for you. Narrow your search by applying the WiFi filter on Vrbo.

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