Brookline vacation rentals
Vacation rentals in Brookline by owner — compare homes, condos and cabins, message verified hosts, and book direct with no service fees.
Brookline is conveniently located near Coolidge Corner, Washington Square, Larz Anderson Park, and the Emerald Necklace. Visitors enjoy cultural experiences like the John F. Kennedy National Historic Site, Brookline Village's charming shops, and ReelAbilities Film Festival events. With Houfy, travelers connect directly with Brookline hosts to book, saving money on every stay. Choose from a variety of rentals such as historic homes, modern apartments, and charming condos near Newton and Cambridge. Brookline's proximity to Boston offers easy access to public transport and attractions throughout the city.
Top-Rated Vacation Homes in Brookline
Browse the highest rated vacation properties in Brookline.
$954.59 USD total for 3 nights
Oct 24 – 27, 2026
This rental was perfect for my family's first visit to Boston! The home is in the quaint area of Jamaica Plain, convenient to the "T" stop at Stonybrook and all Boston has to offer. Also convenient were various delicious places to eat (don't miss Star seafood market) and markets to buy everyday items. The home is well cared for and very updated with great amenities such as keyless entry, a VERY nice kitchen and even a patio out back with vegetable and herb gardens. Perry was fabulous to work with from start to finish, checking up with us to see if we needed anything before our arrival and giving us great local advice after we arrived. This is probably the most well stocked vacation rental I have even been in. We did not want for anything as there were plenty of extra sheets, blankets, towels, pillows, toilet paper - you name it and Perry had stocked it! As we got to know the city of Boston and the mass transit (very easy to use), this was a comfortable home to return to each evening. I highly recommend!
Recommended Homes in Brookline
Handpicked properties we think you'll love in Brookline.
Front Row City Views: 1BR Suite with King Bed | Suite 3
$1,283.11 USD total for 3 nights
Nov 7 – 10, 2026
$2,044.76 USD total for 3 nights
Oct 25 – 28, 2026
$1,847.85 USD total for 3 nights
Oct 28 – 31, 2026
$1,864.26 USD total for 3 nights
Oct 27 – 30, 2026
Elegant 1BR Plus: Sky-High City Views + King | Suite 9
$1,493.68 USD total for 3 nights
Oct 30 – Nov 2, 2026
$1,573.00 USD total for 3 nights
Oct 25 – 28, 2026
Cityscape 1BR Plus: King + Queen Pull-out | Suite 7
$1,225.67 USD total for 3 nights
Nov 1 – 4, 2026
Elegant 1BR Plus: Cityscape Views + King and pull out Queen| Suite 5
Pet friendly vacation rentals in Brookline
Bring your furry friend along! Browse pet-welcoming homes in Brookline.
$1,202.43 USD total for 3 nights
Nov 1 – 4, 2026
$1,553.85 USD total for 3 nights
Oct 18 – 21, 2026
Why visit Brookline
Discover what makes Brookline a perfect vacation rental destination.
Historic Architecture
Explore 19th-century charm.
Stroll down Beacon Street and admire its Victorian-era architecture. Just 1 mile from downtown Brookline, these historic homes are a testament to the town's rich past.
Rich Arts Scene
Home to unique galleries.
Visit the Brookline Arts Center a mere 0.5 miles from the center, which offers rotating exhibitions from local artists. Admission is free, with suggested donations.
Diverse Culinary Options
From delis to fine dining.
Sample the renowned sandwiches at Mike's Deli, only 0.3 miles away, or indulge in French cuisine at La Voile, a short 10-minute walk from the town center.
Beautiful Green Spaces
Visit scenic parks and gardens.
Spend an afternoon at Larz Anderson Park, located just 1.2 miles away, offering hiking trails, picnic areas, and stunning views of the Boston skyline.
Where to stay in Brookline
The best areas and neighborhoods for your vacation rental in Brookline.
Coolidge Corner
Renowned for its vibrant mix of shops, restaurants, and cultural venues. It’s a lively hub perfect for young professionals.
Brookline Village
A historic area with charming boutiques and the popular Brookline Village Farmers' Market every Thursday.
Chestnut Hill
Known for sprawling estates and home to Boston College; ideal for those seeking a more suburban feel.
Jamaica Pond
Features tranquil water views and lush walking trails, great for outdoor activities and relaxation.
Find Brookline vacation rentals that suit your style
Apartments and more — pick the kind of Brookline vacation rental you want, then book it direct with the host.
Brookline vacation rentals with free WiFi, air conditioning or parking
Free WiFi, air conditioning, parking and more — every Brookline vacation rental here is listed by a verified host and bookable direct, with the price the host set.
Top attractions in Brookline
All within driving distance of Brookline vacation rentals.
John F. Kennedy National Historic Site
Visit the birthplace of the 35th president, showcasing early life exhibits. · 1 mile
Olmsted Park
Features scenic walking paths and ponds designed by famed landscape architect Frederick Law Olmsted. · 2 miles
The Larz Anderson Auto Museum
Houses America's oldest car collection just 1.5 miles from Brookline center. · 1.5 miles
Coolidge Corner Theatre
Screens independent films and hosts cultural events regularly. · 0.2 miles
Brookline Booksmith
An independent bookstore known for its extensive collection and author events. · 0.3 miles
Jamaica Pond
Popular for jogging and sailing, offering beautiful landscapes. · 3 miles
Getting to and around Brookline
Brookline is easily accessible by public transit or car, and Boston Logan Airport is just 10 miles away.
- BOSTON LOGAN INTERNATIONAL AIRPORT
- Located 10 miles from Brookline, it's the nearest major airport offering domestic and international flights.
- MBTA GREEN LINE
- Runs through Brookline providing easy access to downtown Boston. Stations include Coolidge Corner and Brookline Village.
- LOCAL ROADS
- Brookline is well-connected by Route 9 and Route 1, with ample street parking and parking garages available.
- BLUEBIKES
- Boston's public bike-sharing system has stations throughout Brookline for convenient short-distance travel.
Similar vacation rentals near Brookline
Homes within 60 miles of Brookline, from verified hosts.
$1,725.00 USD total for 3 nights
Oct 20 – 23, 2026
$1,454.73 USD total for 3 nights
Oct 15 – 18, 2026
$1,667.66 USD total for 3 nights
Nov 1 – 4, 2026
$1,032.75 USD total for 3 nights
Nov 8 – 11, 2026
$4,338.75 USD $3,919.88 USD total for 5 nights
Nov 13 – 18, 2026
$3,931.00 USD total for 3 nights
Oct 19 – 22, 2026
$4,405.10 USD total for 7 nights
Oct 15 – 22, 2026
$1,100.50 USD total for 3 nights
Oct 18 – 21, 2026
$552.00 USD total for 3 nights
Oct 22 – 25, 2026
Explore near Brookline
Cities and towns within driving distance of Brookline, each bookable direct with the host.
Direct with the host
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Verified hosts
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Itemised pricing
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More vacation rental destinations around Brookline
Frequently asked questions
Quick answers about booking vacation rentals in Brookline and what direct booking on Houfy actually means.
The average cost of rentals in Brookline ranges from $150 to $300 per night, depending on the size and location within the area.
Yes, many Brookline vacation rentals on Houfy welcome pets. It's best to check individual listings for specific pet policies.
Chestnut Hill and Brookline Village are great for families due to their parks, schools, and family-friendly events.
Brookline is charming year-round, but spring and fall offer comfortable temperatures and vibrant foliage perfect for exploring.
Brookline offers a range of rentals from cozy apartments in Coolidge Corner to luxury homes in Chestnut Hill.
Vacation rentals provide more space and local charm often at a better price. Homes in Brookline offer unique access to local culture and amenities.
Coolidge Corner and Brookline Village offer local shops, art galleries, and dining options representing a mix of cultures and stories.
Houfy is a direct booking platform where guests contact hosts directly, paying the listed price upfront.
Yes, Houfy prioritizes secure transactions and communication between travelers and hosts, with robust verification systems in place.