Photo by Ed Gaffny

Chestnut Hill holiday rentals

We found 2,247 holiday rentals — enter your dates for availability

Discover a selection of 5 homes and other holiday rentals in Chestnut Hill that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the best amenities for spending time at your holiday home, which might include Wi-Fi and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

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-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Chestnut Hill

Are you hoping to discover top things to see and do while you're in the area? Venture out of your cosy holiday rental and check out everything that makes Chestnut Hill a fun spot to go on holiday. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • New England Aquarium (6.4 mi / 10.4 km)
  • Encore Boston Harbor (7.1 mi / 11.5 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 looking for exciting outdoor activities or just want to appreciate the scenery, Chestnut Hill is a great spot to appreciate mother nature. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Boston Common (5.6 mi / 8.9 km)
  • Copley Square (4.9 mi / 7.9 km)
  • Chestnut Hill Reservoir (1.2 mi / 1.9 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)

Travelling 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 centre. If you're unable to find a flight that fits your schedule, you could book a flight to 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 holiday home?
If you’re planning a holiday in Chestnut Hill, South Brookline is one of the most in-demand locations to stay. Whatever your style of travel, Stayz is bound to have a property here that matches your needs.
What is the most popular type of holiday home accommodation in Chestnut Hill?
Based on our research, apartments are the most desirable type of holiday home in Chestnut Hill. But naturally, everyone’s idea of an awesome trip isn’t going to be the same. Stayz has holiday 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 holiday home in Chestnut Hill?
The average price for a holiday 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 holiday home 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 Stayz by entering the dates you’ll be travelling. 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 holiday homes in Chestnut Hill?
You’re in luck! There are. You’ll have your pick of 13 holiday homes that cater to pets in Chestnut Hill. Lots of our pet-friendly holiday homes 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 Stayz.
What are popular home amenities in Chestnut Hill?
A fireplace, an electric car charging station and a firepit are rated the most popular home amenities in Chestnut Hill. Whether you’re taking to the road alone, with your sweetheart or a group of dear friends, Stayz can help you find a holiday home that matches your style with all the features you need.
Are there large group holiday homes in Chestnut Hill?
Take your pick of three Stayz 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 holiday homes in Chestnut Hill that welcome kids?
Chestnut Hill has 13 family-friendly holiday homes. 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 holiday homes in Chestnut Hill?
Yes, Chestnut Hill has four one-bedroom homes available. Typically located in prime areas because of their smaller size, a one-bedroom holiday property is ideal if you’re travelling 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 holiday homes in Chestnut Hill?
Chestnut Hill has three two-bedroom holiday homes for you to select from. Discover a holiday home with all the space and comfort you want at a price that’s hard to resist on Stayz.
Are there holiday homes with WiFi in Chestnut Hill?
You can pick from four holiday homes with WiFi in Chestnut Hill. If you want to disconnect from daily life while on holiday, but still need to be connected to the web, these getaways are for you. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Chestnut Hill?
You’ll have a choice of 12 holiday homes with air conditioning in Chestnut Hill giving you that gentle, cool breeze and extra bit of comfort. Enter your travel dates and then use our filter tool to help you find properties with air conditioning.
How old do you have to be to rent a holiday home in Chestnut Hill?
The minimum age can differ between properties on Stayz, so double-check the rules of the holiday home in Chestnut Hill you want. But typically, it’s 16, 18 or 21.
How long can I rent a holiday home in Chestnut Hill for?
The length of time you can book a holiday home in Chestnut Hill differs according to the property. Just enter your preferred travel dates to view a list of options offering extended stays. With plenty of amenities like kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you’re sure to find someplace just right to call your home away from home in Chestnut Hill.

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