
Holiday rentals in Brookline
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Top-rated holiday rentals in Brookline
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2 BR APT w/ parking near MIT/Harvard/BU/Fenway
STUNNING, RENOVATED 2 BEDROOM APARTMENT! Keyless entry self-checkin, free street parking. Luxurious getaway with 2 queen memory foam beds, 1 full sofa bed, cable TV, WiFi, walk-in shower, fully equipped kitchen with stainless steel appliances, in unit washer/dryer, hardwood & marble flooring throughout, new heating system. Next to MIT, Harvard, BU, Kendall, Boston, Fenway Park, Red & Green lines, Flour Bakery, Whole Foods & Trader Joes. This 1st floor unit is immaculate & professionally cleaned

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

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

Lovely Boston studio with bedroom and city views!
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.

New Spacious 2B2B Apartment, One Free Parking Spot
Newly renovated spacious 2B2B apartment in the center of Brookline. Steps away from T-Stop, restaurants, cafés, groceries and more. Near Coolidge Corner, Longwood Medical Area, Fenway and BU. Comes with one free parking spot and quality linens, towels, cookware and tableware. It is on garden-level but all windows are above ground. Pets friendly with extra charge $100/pet/stay. Professionally cleaned & sanitized. Separated Air conditioning and heating system to avoid the crowds at hotel.

A Brookline Sanctuary
You're in the heart of Brookline! LOCAL: Minutes away from a French bakery , Thai restaurant, taqueria, liquor store and small grocery store. More restaurants, cafes and bars down the street in Coolidge Corner and Washington Sq. BOSTON: 5-minute walk to subway stop. 10-min subway ride to Fenway Park. Direct subway to tourist spots! Easy transfer to Cambridge . Perfect for visiting Boston, a friend, a student or colleges. Enjoy the entire floor to yourself with a private entrance!

Conveniently Located Private Garden Apartment
Garden-level apartment next to public park, yet convenient to Newton Centre, Chestnut Hill, Boston College, Longwood Medical Area, and public transit. Easy access to Boston area attractions. Sleep late in a comfy bedroom with blackout shades, relax in front of the 55" HDTV, whip up a quick meal in the kitchenette, or enjoy the outdoors sitting on the patio. Come and go as you please with a private entry. Great for quick visits or extended stay. Newton Short Term Rental - STRA-23

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.

Gorgeous Beacon Hill 1BR | 1BA
Come stay at our lovely condo in the heart of Boston's most desirable neighborhood, Beacon Hill! Our newly renovated 1 bedroom | 1 bathroom condo comfortably sleeps three adults and comes with everything you need for an enjoyable stay. Whether you want to walk the Freedom Trail, visit a relative at Mass General, or shop on Newbury St, you will find it all within walking distance. You could not be more centrally located to take in all the city has to offer.

Historic Brookline 3BR w/ Parking
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 $135 one-time fee. Experience the peaceful charm of Brookline from our cozy 3-bedroom apartment, just minutes from the heart of Boston. Perfect for families or small groups seeking comfort, convenience, and a touch of local character.
Popular amenities for Brookline holiday rentals
Other great holiday rentals in Brookline

Walk to Harvard/MIT/BU Near NEU/MGH Comfy & Quiet

Bright 1st-Fl 2BR Near Hospitals

Union Haus - Entire Home|2 King Suites|sleeps 12

Boston Buccaneer Retreat

Sunlit Brookline Victorian.

Steps to the Green Line & Minutes from Boston! #38

1400sqft:1 min>T&Washington Sq/Sleeps8/4Bed2Bath

Modern Brownstone - walk to Longwood Medical Area!
When is the best time to visit Brookline?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $152 SGD | $154 SGD | $170 SGD | $195 SGD | $210 SGD | $201 SGD | $190 SGD | $196 SGD | $191 SGD | $209 SGD | $164 SGD | $153 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.
Quick stats about holiday rentals in Brookline

Total holiday rentals
Explore 1,080 holiday rentals in Brookline

Nightly prices starting at
Brookline holiday rentals start at $38 SGD per night before taxes and fees

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

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

Pet-friendly holiday rentals
Find 240 rentals that welcome pets

Holiday rentals with a pool
90 properties feature pools

Rentals with dedicated workspaces
560 properties have a dedicated workspace

Wifi availability
1,060 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
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