Discover a selection of 1,000 vacation rentals in Brookline 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 $90 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.
Top rated rentals — Brookline
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?

Our 2021 property listings offer a large selection of 1,080 vacation rentals around Brookline. From 878 condo and apartment rentals to 176 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.