Discover a selection of 1,000 vacation rentals in Brookline, 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 WiFi and parking. Prices start at $233 per night, and condos and houses are popular options for a stay in Brookline. Either way, you'll find a rental for everyone's needs.
Destination guide

Vacation rentals in serene Brookline

Book a Brookline vacation rental and immerse yourself in the rustic charm, heritage sights, and lush green space that this small Massachusetts town has to offer. Brookline forms a part of Greater Boston, based just 5 miles southwest of the city’s downtown area, yet it feels a million miles away from the hectic urban energy of the capital. Country clubs, lakeside parks, and unblemished woodland surround Brookline, and the town’s center sings with redbrick storefronts and quaint cafés. Brookline’s vacation rentals – a mix of sunny studious, vast townhouses, and luxury exposed-brick apartments – provide perfect accommodation.

Things to do

Brookline brims with history and heritage

Brookline lays claim to a dazzling piece of American history – it was the birthplace of US President John F. Kennedy. History buffs can visit Kennedy’s childhood home, a family townhouse – now a National Historic Site – on Beals Street, fronted with green-blue timber slats. Visitors can take guided tours of the house, for a greater appreciation of the former president’s life. For more American heritage, see the Larz Anderson Auto Museum, based inside a late 19th-century Chateau-style stone manor. Here, you’ll discover ever-changing automobile exhibits, with perfectly-preserved Ford, Packard, and Dodge cars from the early 20th century.


Shopping and sports in bountiful Brookline

Shopping is a top Brookline activity, as the town boasts a fair share of charming independent boutiques and specialty stores. The Coolidge Corner area is a particularly snazzy shopping spot, celebrating upscale designer clothing and fashion boutiques. If shopping doesn’t spark your interest, how about a round of golf? There are several country and golf clubs dotted in and around Brookline, with 18-hole courses offering peaceful tree-lined thoroughfares. If you’re after a wild outdoor experience, visit Cutler Park Reservation 6 miles southwest of Brookline, which is an enormous nature reserve cris-crossed with hiking trails.


Sun-blushed summer months in Brookline

Brookline experiences 4 distinct seasons, with hot and humid summer months – from June through August – where temperatures regularly hit 80 degrees and above, to very cold winters – December through February – which frequently welcome frost, ice, and snowfall. Some Brookline vacation rentals, particularly the old townhouses, have cozy, picture-prefect wood burning fireplaces that are perfect in these months. While summer is the most pleasant time to travel for outdoor activities, fall, although chilly, sees a vibrant red and gold blanket of foliage fall across Brookline, which makes for a romantic setting.

Natural features

Small town parks meet sprawling wilderness

The bustling city of Boston lies 5 miles from Brookline, and the quiet, residential suburb of Brighton borders Brookline’s east. The grassy waterfront parks and leafy, idyllic country clubs in the southern side of Brookline – like Jamaica Pond, Olmsted Park, and Larz Anderson Park – lead on to larger green spaces. The Arnold Arboretum, for instance, overflows with towering native and Northern Hemisphere trees, creating a lush shady sanctuary. The Cutler Park Reservation offers a wilder taste of nature, where untamed freshwater marshes and forests house red foxes, deer, and rare birdlife.

How to get there

Transportation options to and around Brookline

The nearest airport is in Boston, MA (BOS-Logan Intl.), located 6.2 mi (9.9 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Norwood, MA (OWD-Norwood Memorial), which is 10.3 mi (16.5 km) away.

You can see more of Brookline by catching a ride on the metro at Brookline Hills Station, Fairbanks St. Station or Brandon Hall Station.

How many vacation rentals are available around Brookline, MA?

Our 2021 property listings offer a large selection of 873 vacation rentals around Brookline. From 655 condo and apartment rentals to 160 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Brookline?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Brookline:

  • Longwood: 77 vacation rentals
  • Coolidge Corner South Side: 91 vacation rentals
  • Aspinwall Hill: 37 vacation rentals
  • North Brookline: 34 vacation rentals
  • Central Village: 32 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Brookline?

Vrbo offers a large selection of vacation rentals near lovely places in Brookline. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Coolidge Corner Theatre: 1,057 vacation rentals
  • Washington Square Station: 1,055 vacation rentals
  • Agganis Arena: 988 vacation rentals
  • Brookline Farmers Market: 995 vacation rentals
  • Longwood Station: 1,017 vacation rentals

But there are many other points of interest around Brookline listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Condos/Apartments in Brookline?

Yes, of course. Vrbo has 655 Condos/Apartments in Brookline. Our other popular types of vacation rentals in Brookline include:

  • Houses: 160 rentals available
  • Studios: 616 rentals available
  • Townhouses: 13 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Villas and more.

Can I find a vacation rental with pool in Brookline?

Yes, you can select your preferred vacation rental with pool among our 51 vacation rentals with pool available in Brookline. Please use our search bar to access the selection of vacation rentals available.