
Holiday rentals in Brookline
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Quick stats about holiday rentals in Brookline

Total holiday rentals
Explore 1,030 holiday rentals in Brookline

Nightly prices starting at
Brookline holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 50,620 verified reviews to help you choose

Family-friendly holiday rentals
390 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 240 rentals that welcome pets

Holiday rentals with a pool
80 properties feature pools

Rentals with dedicated workspaces
570 properties have a dedicated workspace

Wifi availability
1,010 of Brookline holiday 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
Top-rated holiday rentals in Brookline
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

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! Entire apartment. No shared spaces. 100% private. Parking included.

Sunlit Brookline Victorian.
Centrally located on a quiet residential street within a short, pleasant walk to local shops, cafes, restaurants, museums, Boston College, Boston University, Longwood Medical area, and Fenway Park. Washington Square T-stop is around the corner, connecting with the rest of metro Boston. Whole Foods, Trader Joe's, and Star Market are within 10 minutes walk. An easy ride to Logan Airport or historical towns of New England. Free two car garage parking, back porch dining area.

The Galen: Luxe Leisure • Elevated • Amenities!
Experience Boston in this beautiful 2BR unit near the heart of the city! Just a 5 min walk from the T and close to Boston College/Harvard, you can tastefully engage with all of Boston. Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 50” Roku TV Master Bedroom -> Fully Stocked Kitchen -> Washer & Dryer -> 1 Queen Bed -> 1 Full Bed -> 1 Rolling Twin Bed Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

Kasa Boston at Fenway | Two Bedroom
With its prime location and exceptional amenities, Kasa Boston at Fenway is the ideal home in the heart of the city. Enjoy our fully furnished apartments with kitchens, in-unit laundry, and access to the fitness center. Just steps from Fenway Park, the Longwood Medical Area, restaurants and attractions, it’s perfect for short visits or extended stays. Our tech-enabled apartments offer 24/7 guest support through our Virtual Front Desk accessed via mobile device.

Coolidge Corner-1st Floor-Close to the Subway!
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.

Steps to the Green Line & Minutes from Boston! #28
In the heart of Coolidge Corner right off the Green Line, our picturesque studio apartment is a quick train ride to Fenway, Faneuil Hall and the Back Bay. Our space is perfect for solo adventures, business travel, or visiting students at the many neighboring universities. Sleep comfortably on pillow-top mattresses. Other features include heated bathroom floors and shared beautiful stainless steel full kitchens with crafted Italian Granite counter tops.

Walk- Close to Public Transp - Family Neighborhood
Beautiful and spacious 2 beds / 1 bathroom apartment in a family friendly neighborhood. Location location location! A few mins walking to T (subway). Super safe and one of the coolest neighborhoods in town. Walk everywhere! This super convenient neighborhood is steps from local gems: Trader Joe's, Target, and the vibrant Coolidge Corner Theatre. Hop on the T and you'll be only 4 stops away from Fenway Park, Kenmore Square, and Back Bay.

Beautiful Top floor apartment
Located in Washington Square. Easy walk to 3 train lines. Close to Boston College. Mecca for several award winning restaurants and beautiful quiet tree lined streets. Top floor of owner occupied home newly renovated with new furnishings and a private bath. There are 2 bedrooms and a large living room with a tv and upright piano. There is a kitchenette with a new convection oven, Air fryer, Espresso machine and fully stocked kitchen.

1 free parking spot - Walk to subway - Location!
Lovely apartment in the heart of Boston. Prime location. Very safe & one of the coolest neighborhoods in town. Hop on the T and you'll only be a few stops away from Fenway Park, Kenmore Square, & Back Bay. 1 Free parking spot included. Close to Boston University, BC, Downtown, Cambridge, John F. Kennedy Birthplace Museum, Coolidge Corner, Longwood Medical Area, supermarkets, restaurants, bars, theater, shops, stores, and more!

King Bed | 3 min > Washington Sq | 1 min >T
I've hosted & co-hosted for 4 years. All questions are answered here so you can make an informed decision. 🐾 Pet-Friendly Stay! We welcome pets under 20 pounds for a $175 one-time fee. Guests will be responsible for any damages caused by their pets. Experience the peaceful charm just outside of Boston from our cozy 1-bedroom apartment, located on the 3RD FLOOR about 40 steps (please note: NO elevator access).
Popular amenities for Brookline holiday rentals
Other great holiday rentals in Brookline

Private room at Coolidge corner, near Subway

Cozy quiet room C (NearBU/Fenway/Downtown/HMS)

2 FREE parking spots- In unit washer/dryer

①min>Coolidge | Full Kitchen- 2

Queen Ann Brookline B&B M605 #2

Beautiful room, historic home, fantastic location.

Boston Children's, Beth Israel, Dana Farber, Brigham

Coolidge corner entire 1bed apt
When is the best time to visit Brookline?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $155 SGD | $151 SGD | $164 SGD | $199 SGD | $215 SGD | $206 SGD | $194 SGD | $201 SGD | $195 SGD | $214 SGD | $168 SGD | $157 SGD |
| 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.
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- Fenway Park
- Harvard University
- Hampton Beach
- TD Garden
- Gillette Stadium
- Boston Common
- Boston Seaport
- Revere Beach
- Brown University
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- New England Aquarium
- Onset Beach
- MIT Museum
- Canobie Lake Park
- Crane Beach
- Duxbury Beach
- North Hampton Beach
- Boston College
- Roxbury Crossing Station
- Northeastern University
- Quincy Market
- Tufts University
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