
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.

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. We declined ALL requests for dates >6 mos ahead/not open yet

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.

Cozy Apartment - BU/Fenway/Longwood- Free Parking!
Our cozy apartment is located on a quiet street, steps from many popular restaurants, cafes and bars. One parking spot is also provided! Located only a 5 minute walk to the Green Line subway, 2 miles to Downtown Boston, 0.3 miles to Boston University, 0.5 miles to Fenway, and 0.5 miles to Longwood (Beth Israel, Brigham & Women’s, Dana Farber and Children’s Hospital). We're also less than a mile from many of the cities best attractions - Kenmore Square, Newbury St, Back Bay and so much more.

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

New 3 bedroom, 2 bath unit, meadow view!
Located on the 2nd floor of a brand-new building, this modern unit is perfect for family and group trips! Living in this quiet, residential neighborhood, you will be minutes away from many universities (BC, BU, Harvard, MIT, NEU, etc.), downtown Boston, and many major attractions (Boston Common, Newbury Street, Freedom Trail, etc.). Relax and enjoy the peaceful meadow views at the back of the building. Subway stations, bus stops, and restaurants and grocery store are within walking distance!

2 Bed Apartment-BU/Fenway/Longwood -free parking!
Our spacious 2 bedroom apartment is set on a quiet street in a vibrant area. We are located steps from many popular restaurants, cafes and bars. One parking spot is also provided! Located just 2 miles west of Downtown Boston, 0.3 miles to Boston University, 0.5 miles to Fenway Park, 0.5 miles to Longwood Medical, & 5 minute walk to the Green Line subway. We're also less than a mile from many of the cities best attractions including Kenmore Square, Newbury st, Back Bay and so much more!

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.

1 free parking spot - Walk to subway - Location!
Beautiful 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!

Pretzel Factory Loft w/Peloton
Creative loft style house that is home to a fashion designer and her family! Two floor loft like living very centrally located in Brookline MA. Very centrally located in Brookline Village. A few minutes walk to the T and very close to the hospital district. Whole house perfect for the whole family with fast Wifi and garage parking. Search for 'Everywhere Architecture' & click on 'White Place' to see more pictures!

Luxury 2B1B Apt. Amazing Location
Completely renovated 2B1B apartment in the central of Brookline. The full kitchen has everything you need. One king bed in the master bedroom, two full beds in the second bedroom. This is a Garden-level unit with a free parking space. A short walk to T-Stop, restaurants, cafés, groceries and more. About 1 mile to Longwood Medical Area, Fenway and BU. Our places are professionally cleaned & sanitized.

Private Carriage House near Newton Center and BC
Large studio above garage with private entrance located on famous Heartbreak Hill. Kitchenette with Fridge, Microwave, Keurig and full bathroom. Less than 1 mile to Boston College and just minutes to Cambridge and Boston. Easy walk to public transportation and Newton Center with great restaurants, bars, parks, and shopping. Free off-street parking.
Popular amenities for Brookline vacation rentals
Stay near Brookline's top sights
Other great vacation rentals in Brookline

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee

All the comforts of home, quiet city neighborhood

2Bedroom - WALK to subway, hospitals, food, & more

①min>Coolidge | Full Kitchen- 2

A Brookline Sanctuary

Cozy studio apartment in Jamaica plain!

Washer+Dryer+Parking!*Private suite*Cul de sac*

Location - Walk to Subway - Safe and clean
Quick stats about vacation rentals in Brookline
Total rentals
1K properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
47K reviews
Family-friendly rentals
410 properties are a good fit for families
Pet-friendly rentals
240 properties allow pets
Rentals with a pool
100 properties have a pool
Frequently Asked Questions
Where should I stay in Brookline?
Make yourself at home in Brookline by choosing from our most frequently booked neighborhoods. We have over 1,770 vacation rentals in Longwood, over 1,770 vacation rentals in Chestnut Hill, and over 1,770 vacation rentals in North Brookline.
Are there vacation rentals with a dedicated workspace in Brookline?
Yes! Work meets play with ease at over 550 vacation rentals in Brookline featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Brookline?
Four-legged friends are welcome in Brookline. Choose from more than 260 vacation rentals for guests traveling with pets.
Do apartment rentals in Brookline have a bbq area?
Absolutely! We offer over 20 apartment rentals with a bbq area in Brookline. Enjoy a tailored experience with all the comforts you desire.
Are there Brookline apartment rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 100 apartment rentals with pools in Brookline, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly house rentals in Brookline?
Brookline has more than 80 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do hotel rentals in Brookline have wifi?
Absolutely! We offer over 20 hotel rentals with wifi in Brookline. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Brookline have a gym?
Absolutely! We offer over 140 apartment rentals with a gym in Brookline. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in bed and breakfast rentals in Brookline?
Experience the best of Brookline with our bed and breakfast rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for Boutique Hotel Rentals in Brookline?
Enhance your stay in our Boutique Hotel Rentals with the most popular amenities: over 10 homes with a gym, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
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