Vacation rentals in Brookline

Guest suite in Jamaica Central - South Sumner

A spacious studio features a comfortable bed with a decorative pillow against the warm wood headboard. Soft, natural light fills the room, highlighting the wooden floors and cozy seating area. A kitchenette is visible in the background with cabinets and a small coffee setup.

4.92 out of 5 average rating, 233 reviews

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 and sink but no stove or cooking. Pls don't request to book more than 6 months in advance.

5 out of 5 average rating, 113 reviews

The living area features a high, sloped ceiling with exposed wooden beams. A comfortable sectional sofa is complemented by colorful cushions. A coffee table is positioned in front of the sofa, while a television is situated nearby, enhancing the inviting space with soft lighting from a floor lamp.

Apartment in Allston

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.

Apartment in Fenway-Kenmore

A living room features light green walls and hardwood flooring. A gray sofa is complemented by colorful accent pillows. A round table with a decorative item is visible beside a patterned chair. Natural light enters through a nearby window, enhancing the cozy atmosphere.

4.81 out of 5 average rating, 287 reviews

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.

Apartment in Fenway-Kenmore

A spacious living room features a large sectional couch and a coffee table on a decorative area rug. An elegant chandelier hangs from the ceiling, while decorative wall art adds character. A lamp provides soft lighting next to the couch, enhancing the cozy atmosphere.

4.84 out of 5 average rating, 292 reviews

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!

4.82 out of 5 average rating, 302 reviews

A modern kitchen is equipped with stainless steel appliances, including a microwave and stove. Dark cabinetry contrasts with the light countertops, which are complemented by a granite finish. A coffee maker and kettle are visible, alongside a red pot on the stove.

Guest suite in Brighton

Large Studio Apt w/ Full Kitchen & Bath + Parking!

Close to all Universities, Hospitals and Tourist Sites. Walk to the Green Line T (subway) and tons of bus routes. Gourmet kitchen fully stocked. Hotel style bathroom. Queen size bed with nice mattress + well appointed furniture. Off street parking included! Registered Short Term Rental. This Boston location can't be beat for the price. Close to Boston College, Harvard University, Boston University. Walk to restaurants, coffee, and shops. Quick access to I90 and Storrow Drive.

4.92 out of 5 average rating, 344 reviews

A well-lit room features a light-colored wall and a window with sheer curtains. A sleek desk and chair are positioned beside a white dresser. A framed artwork is displayed on the wall, adding a touch of character to the space.

Guest suite in Brighton

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

Bright spotless studio with private entrance to the ground level of a single family home. Ample street parking. Peaceful family neighborhood minutes from the Green line. Near BU, BC, St. E's, Coolidge Corner, Cleveland Circle, Washington Square. 30 minutes from downtown Boston. Ideal for professionals, tourists, student, or visiting parents. Hassle free with all basic amenities. Micro kitchen (no stove or oven), Central air, heat, Wi-Fi, private washer/dryer.

4.86 out of 5 average rating, 238 reviews

The modern kitchen features light-colored cabinetry and sleek countertops. Oversized windows allow ample natural light, illuminating the dining area. A central table accommodates seating for six, and various appliances are neatly arranged on shelves and counters, enhancing the functionality of the space.

Condo in Brookline

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.

Guest suite in Jamaica Plain

A cozy corner is visible, featuring an upholstered chair beside a vintage table lamp. Two skylights allow natural light to fill the space. A small table holds plants, and colorful rugs create a warm atmosphere while leading to an inviting bedroom beyond.

4.97 out of 5 average rating, 304 reviews

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.

4.92 out of 5 average rating, 139 reviews

A spacious living area features a mix of comfortable seating, including a large sofa and a cozy armchair. Natural light streams through multiple windows covered with woven shades. Shelves filled with books and decorative items line one wall, while a light-colored rug adds warmth to the concrete floor.

Home in Brookline

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!

4.97 out of 5 average rating, 102 reviews

A spacious living area features a comfortable brown leather sofa and a blue armchair. A wooden coffee table sits in the center, and a 55-inch television is positioned on a console against a light blue wall. Large windows allow natural light to fill the space.

Condo in Jamaica Plain

2 Bedroom by Longwood Medical Hospitals

Perfect location for those visiting Longwood Medical area hospitals. Walkable area with a train that goes anywhere in the city, directly across from tons of green space. Enjoy a restful night sleep on a king sized memory foam mattress or full memory foam in second bedroom. You will be entertained with Roku & streaming (55in TV). Updated kitchen stocked with coffee.

Guesthouse in Chestnut Hill

A spacious studio features natural wood beams overhead and a combination of seating areas. A comfortable bed is positioned alongside a decorative side table. A dining table with chairs is visible, and light streams in through the windows, enhancing the bright and inviting atmosphere.

4.94 out of 5 average rating, 128 reviews

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.

Condo in Jamaica Central - South Sumner

A historic brick brownstone is shown from the street, featuring a classic architectural style with bay windows. The building is framed by vibrant green trees and neatly trimmed bushes, contributing to the residential charm of the neighborhood.

4.88 out of 5 average rating, 556 reviews

Historic JP Brownstone with Parking. Pets Welcome!

Located in one of Boston's best neighborhoods, this 1200 square foot bright sun filled corner unit in a 120 year old historic Brownstone is the perfect retreat. Its excellent location is just steps from the T and a short walk to Centre Street shops and restaurants. Good for couples, solo adventurers, business travelers, and furry friends (pets).

Vacation rentals for every style

Get the amount of space that is right for you

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Convenient locations with everyday essentials

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Popular amenities for Brookline vacation rentals

Monthly stays

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Brookline's top sights

Boston University123 locals recommend

Fenway Park935 locals recommend

Museum of Fine Arts1,137 locals recommend

Other great vacation rentals in Brookline

A light-filled studio features a spacious bed with plush pillows and modern bedding. A colorful art piece adorns the wall above the bed, complemented by a cozy area rug. Nearby white cabinetry and a closet offer storage solutions, enhancing the room's functionality.

Loft in Coolidge Corner

4.74 out of 5 average rating, 275 reviews

Steps to the Green Line & Minutes from Boston! #33

Apartment in Coolidge Corner

5 out of 5 average rating, 4 reviews

①min>Coolidge | Full Kitchen- 2

5 out of 5 average rating, 6 reviews

The image displays a vibrant game area featuring a vintage arcade machine alongside a stylish, modern kitchen. A cozy bedroom with a spacious bed and decorative pillows is seen, as well as a dining space with a round table and upholstered chairs.

Home in Coolidge Corner

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

Apartment in Coolidge Corner

A small dining area features a round white table with two yellow chairs. A simple floral arrangement sits atop the table. Overhead lighting brightens the space, while a colorful artwork adorns the wall. Bench seating is available along the nearby wall.

4.97 out of 5 average rating, 31 reviews

A Brookline Sanctuary

The living room is designed with a sectional sofa in a dark hue, paired with a circular coffee table. A large area rug covers the hardwood floor, while soft lighting softly illuminates the space. Tall windows are dressed with sheer curtains, allowing natural light to filter in.

Home in Brookline

4.92 out of 5 average rating, 245 reviews

Modern townhome,Boston vacation,2 bath,pkg,deck

Guesthouse in Chestnut Hill

The open living area showcases a light-filled space with a comfortable gray sofa facing a large set of glass doors that lead to a private terrace. A glass dining table is surrounded by modern white chairs, with sunflowers adding a touch of color on the counter.

4.99 out of 5 average rating, 84 reviews

Sunny 1BR w views, close to BC and Boston

Townhouse in Coolidge Corner

A charming porch is lined with wooden flooring and framed by white columns. Planters with greenery enhance the natural ambiance. Benches provide seating while sunlight filters through the canopy of surrounding trees, creating a serene outdoor space.

4.95 out of 5 average rating, 21 reviews

Sunlit Brookline Victorian.