Brookline, MA, USA

Brookline, MA, USA

We found 1,447 vacation rentals — enter your dates for availability


Find the best place to stay — Brookline

Where to stay near Brookline, MA?

Our 2018 property listings offer a large selection of 1,447 vacation rentals near Brookline. From 852 apartments to 219 condos, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Brookline for a holiday or a weekend are on HomeAway.

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.

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.

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.

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.

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.