Discover a selection of 1,000 vacation rentals in Chestnut Hill, MA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $121 per night, and houses and condos are popular options for a stay in Chestnut Hill. Either way, you'll find a rental for everyone's needs.
Destination guide

Take in the lush beauty of Chestnut Hill

The forests and surrounding scenery provide a peaceful ambiance to your vacation home in Chestnut Hill. Renowned for its university setting, football games and bird watching, this city welcomes all visitors. Boston Museum of Fine Arts and Fenway Park are just a couple of the must-sees in the area. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.


Sightseeing in and around Chestnut Hill

Are you searching for attractions to visit during your stay? Venture out of your vacation home and experience everything that Chestnut Hill has to offer. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • New England Aquarium (6.4 mi / 10.3 km)
  • Franklin Park Zoo (4.1 mi / 6.5 km)
  • Artisans Asylum (5.3 mi / 8.5 km)
  • Blue Hills Ski Area (7.7 mi / 12.3 km)
  • F1 Boston (9.3 mi / 15 km)
  • Fun and Games Family Entertainment Center (12 mi / 19.3 km)
Natural features

Exploring the natural landscape of Chestnut Hill

Whether you're an outdoor enthusiast or just want to take in the scenery, Chestnut Hill is a great spot to appreciate mother nature. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Boston Public Garden (5.4 mi / 8.7 km)
  • Boston Common (5.6 mi / 9 km)
  • Walden Pond (12.5 mi / 20.1 km)
  • Arnold Arboretum (2.4 mi / 3.9 km)
  • Back Bay Fens (4 mi / 6.4 km)
  • Charles River Esplanade (5.3 mi / 8.5 km)
How to get there

Transportation to and around Chestnut Hill

Fly into Boston, MA (BOS-Logan Intl.), the closest airport, located 8.1 mi (13 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Norwood, MA (OWD-Norwood Memorial), which is 9.1 mi (14.7 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.

How many vacation rentals are available around Chestnut Hill, MA?

Our 2020 property listings offer a large selection of 809 vacation rentals around Chestnut Hill. From 96 house rentals to 633 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a city-center property in Chestnut Hill?

Roll out of bed and stroll to those must-see attractions. Or simply get caught up in the excitement and energy of the city! Spend your next vacay living like a local in the middle of the main streets, with a city centre vacation home. Vrbo has 108 city center vacation properties available. Alternatively, you might be interested in trying a different style of vacation setting. Vrbo has a whole lot of options, including:

  • 26 beach vacation rentals.
  • 18 seaside vacation rentals.
  • 10 shore-front vacation rentals.

Can I rent an apartment in Chestnut Hill?

There's no need to say goodbye to the conveniences of home just because you're going on vacation. Kick back and relax in an apartment and soak up the area like a local. Vrbo has 244 for you to browse here. How does $50 per night sound? That's what you could be paying if you don't leave it too long! If that doesn't fit with your family's taste, we have a range of other rental options available, such as:

  • Hotel: 112 vacation homes. Prices start from $28 per night.
  • Condo: 74 vacation homes. Prices start from $75 per night.
  • House: 67 vacation homes. Prices start from $58 per night.

Can I stay in Chestnut Hill in a large group?

There's nothing more enjoyable than staying somewhere entirely new with extended family and friends. The best news is Vrbo has some options to suit large groups. Why not have a peek at the 32 apartment vacation homes listed here? They're the top option for big groups of guests. Properties for rent around here that can house large groups include:

  • If yours is a squad of 6, we've got 138 vacation homes just right for that size. Book a night for as little as $90.
  • Looking for a vacation property for 5 people? We have 95 that will suit. Prices begin at just $65 a night.
  • Searching for places for rent suitable for 8 guests? You'll be thrilled to hear we have 66 that'll be perfect. You can get one from just $169 per night.

So don't fear! When you book with us you can take your aunt, your sister and all your besties to Chestnut Hill.

Where are the cheapest rentals in Chestnut Hill?

Vrbo has a variety of fantastic cost-effective rentals. Treat your gang to a fancy night out or stay a few extra nights with all the dollars you have left over. Jamaica Plain is heaven for bargain hunters. And with 157 Vrbo rentals at an average price of $283 a night, it's not hard to see why. Another 167 Vrbo rentals are available in or around Charlestown. With an average price of $296 a night, you're sure to grab a deal worth bragging about.

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