
Vacation rentals in Brookline
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Top-rated vacation rentals in Brookline
Guests agree: these stays are highly rated for location, cleanliness, and more.

Artistic charm in hip J.P.
It's a quaint efficiency apartment with a private entrance, private bathroom, full kitchen, eat in area and a work space. The bedroom is roomy with a comfy bed perfect for a single traveler or a couple. The apartment is thoroughly cleaned for each guest and all bedding is washed prior to your stay. 5 minute walk to the MBTA train downtown. 10 walk to the bus to hospitals and Museum of Fine Arts. Close to Jamaica Pond and many parks, restaurants, Sam Adams Brewery, grocery shops and bike rentals.

Ann and Esther's Cozy Studio near the Heart of JP
This airy and light private studio is set in a beautiful, secluded backyard/garden. Close to restaurants, shops and acres of green space. Your reservation confirms that you have read "Other Things to Note" in The Space section below and "House Rules" before booking. Guests can only book for themselves. We are 5-7 minutes from the 39 bus and 15 from the Orange line. There is microwave, fridge, counter w/ sink. No stove or cooking. DO NOT request >6 mos ahead. Insta-Book when calendar opens

Newly renovated Brookline 1bd Apartment
Private, fully updated apartment in the heart of Brookline Village near Longwood Medical Center. Enter through a private entryway. The unit has a full kitchen, dishwasher, oven and a refrigerator. The living room has a couch and tv with cable. Unit includes washer-dryer, wifi, and utilities. Many restaurants/ shops/ grocery minutes from away. Close access to public transportation. We live upstairs with 2 young kids. Guests may hear them around 7am. Brookline Short Term Rental License # 2023-1

Brookline - Mod Apartment in Classic Neighborhood
So convenient! Walk to Boston U., Coolidge Crnr, Fenway Park and Allston Village for shopping, restaurants, entertainment. Just 3 miles from downtown. 2 blocks from MBTA Station-easy commute to Longwood Med Ctr, Harvard, MIT, Boston College, the Financial District and more. Beautiful, spacious, newly renovated one bedroom apartment – open floor plan, fabulous kitchen and spa bathroom. Designer furnishings throughout and fully equipped. Ideal for the long term biz traveler or couples on holiday.

Peaceful Country Home, Dover, Ma: Private Entrance
Graceful country oasis in a renovated 125 year old historic home, 35 minutes driving time from downtown Boston. (Important-stair climbing required to reach bedroom suite.) I welcome quiet, mature guests as this is a very peaceful (non-party)environment. We are located on a scenic road in sophisticated Dover, Ma, a commuter/country setting, with miles of hiking trails and roads ideal for cycling. I have owned and loved this home for 35 years and take great joy in its charm and outdoor spaces.

1 FREE parking spot - Coolidge Corner-Close to T
Beautiful flat in the heart of Coolidge Corner. Prime location, a few blocks to the T (subway). Very safe & one of the coolest neighborhoods in town. Hop on the T & you'll only be a few stops away from Fenway Park, Kenmore Sq. & Back Bay. Close to Boston Uni., BC, Downtown, Cambridge, John F. Kennedy Birthplace Museum, Coolidge Corner, Longwood Medical Area, supermarkets, restaurants, bars, theater, shops, stores & more! 1 shampoo/conditioner/shower gel/lotion. 1 loofah & 2 toothbrushes inc

Fully-Equipped 2nd Floor 1-Bed 1-Bath Apt
Discover serenity in this fully-stocked, 2nd floor unit within a Victorian home in JP. Located on a quiet street near transportation and dining options, it offers access to key destinations like Longwood Medical Area and Downtown Boston. Featuring one bedroom, a cozy living room w/ TV, fully-equipped kitchen, and bathroom, plus a spacious private deck. Rest easy on a plush king-size Tempurpedic bed & a full-sized pullout couch fitting 1 adult or 2 children. Central air for increased comfort.

The Watkins : Elevated Cozy • W/D • Amenities!
Experience Boston in a beautiful luxe jr. 1 bedroom unit! Just a 5 min walk from the T and close to Boston College/Harvard, you can engage with all of Boston and tastefully long term. Unit Features -> Blazing Fast WiFi -> 65” SmartTV with Streaming -> Fully Stocked Kitchen -> Washer & Dryer -> Comfortable Queen Bed ->Game rooms all across the property Ideal for business travelers, couples, nurses, those in hospital treatment and everyone looking to experience Boston in comfort and peace.

Coolidge Corner-Walk to Subway-Safe and clean
1 Free Parking Spot! Located just a few blocks from the T (subway). Boston University is right around the corner, and Coolidge Corner, with its cafés, restaurants, theaters, and shops. Hop on the T and you’re only a few stops from Fenway Park, Kenmore Square, and Back Bay. The Longwood Medical Area is also nearby, making it an ideal location for students, professionals, and visitors alike. With supermarkets, coffee shops, pharmacies, and local bars all within walking distance.

Walk to Subway - One Free Parking Spot - Location!
Beautiful 2 bedroom/1 bathroom apartment in Coolidge Corner with a 1 free parking spot! In front of public transportation (Green Line). Walk to great restaurants, cafés, Trader Joe’s, Stop & Shop, local shops, and the Coolidge Theatre. Enjoy quick access to Longwood, BU, BC, Fenway, and downtown Boston. The apartment offers cozy bedrooms, and a well-equipped kitchen, ideal for work trips, medical stays, or exploring the city comfortably, conveniently, and with ease.

Luxurious Townhouse Close to Coolidge Corner
This elegant Châteauesque penthouse was originally built circa 1890 and has been gut-renovated to its full grandeur. The kitchen and dining area features oversized windows that flood the space with natural sunlight. The chef’s kitchen is perfect for cooking and entertaining. Four beautiful and spacious bedrooms for guests to rest and relax. One parking space for a compact car is included for guests as well as easy walk to the T and an easy train ride downtown.

Private & serene getaway in beautiful JP
Quiet, private & serene walk-up 3rd floor apt. Separate entrance, full bath & kitchenette. Bright and spacious. 3 blocks from the center of JP with great restaurants and shopping. 5 min. walk to the 39 bus to Longwood Area and Back Bay. 15 min. walk to the Orange Line T (subway); 1/2 block from Jamaica Pond. 5 min. walk to the Arboretum. Our space is NOT good for people with large luggage! Tons (truly) of street parking, no permit or restrictions.
Popular amenities for Brookline vacation rentals
Other great vacation rentals in Brookline

Charlesgate Suites: Renovated & Ready To Host You!

The Enchanted Willow Storybook Boston Escape 3BDR

Steps to the Green Line & Minutes from Boston! #28

Victorian Treetop Apartment - Close to Everything!

A Brookline Sanctuary

All new 2-bedroom garden apartment on great block.

King Bed | 3 min > Washington Sq | 1 min >T

Boston Children's, Beth Israel, Dana Farber, Brigham
When is the best time to visit Brookline?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $165 CAD | $168 CAD | $184 CAD | $211 CAD | $228 CAD | $218 CAD | $206 CAD | $213 CAD | $207 CAD | $227 CAD | $178 CAD | $166 CAD |
| Avg. temp | -1 °C | 0 °C | 4 °C | 9 °C | 15 °C | 20 °C | 23 °C | 23 °C | 19 °C | 13 °C | 7 °C | 2 °C |
Frequently Asked Questions
What are the best places to stay in Brookline?
Accommodations near Coolidge Corner and Washington Square are frequently suggested for their walkability and access to dining, shops, and parks. Many stays feature home-like amenities suitable for couples, families, or groups.
What are the best things to do in Brookline with kids?
Families frequently visit the playgrounds and picnic spots at Larz Anderson Park and interactive programs at the Brookline Public Library. Seasonal community festivals and farmers markets are also popular with children.
What are some of the best things to do in Brookline?
Explore historic sites like the John F. Kennedy National Historic Site, stroll local farmer’s markets, or enjoy performances at the Coolidge Corner Theatre. Brookline has inviting green spaces and diverse dining options.
How is the weather in Brookline?
Brookline has cold winters around 23–39°F (-5–4°C) with some snowfall, and warm summers between 65–82°F (18–28°C). Spring and autumn usually bring mild temperatures and regular rain.
When is the best time to visit Brookline?
Late spring and early autumn are often recommended for mild temperatures and colorful foliage. Summer brings community events and outdoor dining, while winter invites quieter city moments.
What are the best places to visit in Brookline?
Explore Coolidge Corner for boutiques and cafes, the John F. Kennedy National Historic Site for local history, and Larz Anderson Park for gardens and green space. Each area has a distinct neighborhood atmosphere.
What are some hiking trails in Brookline?
Brookline has gentle walking paths in Hall's Pond Sanctuary and wooded trails in the Dane Park area. Many visitors also enjoy the scenic landscapes at Larz Anderson Park.
What are some family activities we can do in Brookline?
Families often enjoy playgrounds at Larz Anderson Park, interactive exhibits at local museums, and public library programs. Seasonal markets and community festivals provide family-friendly options throughout the year.
What are some of the best day trip ideas from Brookline?
Many travelers explore the historic sites around Boston, coastal communities, or nearby hiking areas. Popular options include local art museums, beaches, and scenic parks just outside the city.
Are there any pet friendly accommodations available in Brookline?
Many accommodations in Brookline welcome pets, especially in areas near parks and green spaces. Always confirm a place's pet policy before booking your stay.
What are some local tips for visiting Brookline?
Exploring neighborhoods on foot or by public transit is often suggested for discovering local shops and cafes. Street parking can be limited, so checking regulations ahead of time is helpful.
What is Brookline known for?
Brookline is known for tree-lined streets, historic architecture, and a mix of urban and suburban charm. The area has notable cultural sites and is home to the John F. Kennedy National Historic Site.
What are the best hidden gems to explore in Brookline?
Wander through the gardens at Larz Anderson Park or the tree-lined paths at Hall's Pond Sanctuary for quieter moments. Local bookstores and independent shops tucked in neighborhood streets invite exploration.
What are the best foods to try in Brookline?
Brookline has locally rooted flavors, including bagels, deli sandwiches, and an array of international cuisine. Bakeries and small cafes around Coolidge Corner are often suggested for pastries and coffee.
What should I bring for a trip to Brookline?
Pack layers for variable weather, especially in spring and autumn when temperatures can change quickly. Comfortable walking shoes are helpful for exploring neighborhoods and parks.
What is the nightlife in Brookline like?
Brookline's nightlife has a relaxed feel with neighborhood pubs, wine bars, and casual cafes. Live music and comedy events can be found around Coolidge Corner and Washington Square.
What are the most popular events or festivals in Brookline?
Brookline hosts community events such as outdoor summer music series, arts and craft fairs, and cultural celebrations. Seasonal farmers markets are also often recommended for local flavor.
Are there family friendly vacation rentals in Brookline?
Brookline has many vacation rentals suited for families, with options near parks, schools, and local attractions. Many stays feature kitchens and living spaces, making it easier to relax together.
Quick stats about vacation rentals in Brookline

Total vacation rentals
Explore 1,080 vacation rentals in Brookline

Nightly prices starting at
Brookline vacation rentals start at $41 CAD per night before taxes and fees

Verified guest reviews
Over 49,280 verified reviews to help you choose

Family-friendly vacation rentals
380 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 240 rentals that welcome pets

Vacation rentals with a pool
90 properties feature pools

Rentals with dedicated workspaces
560 properties have a dedicated workspace

Wifi availability
1,060 of Brookline vacation rentals include wifi access

Popular amenities for guests
Guests love Monthly stays, Gym, and BBQ grill across Brookline rentals

4.7 Average rating
Brookline stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Brookline’s top spots, include Jamaica Pond, Reservoir Station, and Brookline Village Station
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