Vacation rentals in Brookline

Guest suite in Jamaica Plain

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, 234 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.

Superhost

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, 288 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.

4.84 out of 5 average rating, 293 reviews

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.

Apartment in Brookline

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!

4.92 out of 5 average rating, 345 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.

Superhost

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

4.86 out of 5 average rating, 238 reviews

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.

4.96 out of 5 average rating, 437 reviews

A spacious living area features soft furnishings with patterned upholstery and a light-colored coffee table. Natural light filters through the large windows draped with sheer curtains. The kitchenette is visible, along with a small dining table and chairs, creating a welcoming environment.

Apartment in West Newton

Sunny apartment in gracious Victorian

Relax into your Boston stay! We offer a sunny in-law apartment on the first floor of a gracious owner-occupied Victorian house. Quiet, safe residential neighborhood. Private entrance. Spacious bedroom, living room with sofabed, kitchenette & bath. Strong Wi-fi. Driveway parking. Contactless check-in, Easy access to Boston, Cambridge, Rts. 128 & 90, and Charles River bike path. Let us welcome you!

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.

4.88 out of 5 average rating, 556 reviews

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.

Condo in Jamaica Plain

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).

4.96 out of 5 average rating, 368 reviews

A spacious living area features a high wood-beamed ceiling and large windows overlooking greenery. A comfortable couch and plush chairs are arranged around a coffee table. A staircase leads to a loft area, and a flat-screen TV is visible in the background.

Apartment in Fort Hill

Light-Filled Luxury Apartment with View

Beautiful top floor luxury apartment in stately Victorian home. Extraordinary views of historic park as your front yard! Your own entrance through a private garden. Apartment is a studio-style open living space with full kitchen, living area, and bedroom bay with queen bed. Also includes loft bedroom with 2 twin beds.

Guest suite in Newton Corner

A spacious living area features a sectional sofa and a wooden coffee table on a patterned rug. A single armchair in a rich hue complements the brick chimney, while natural light enters through a large skylight, enhancing the comfortable atmosphere.

4.98 out of 5 average rating, 685 reviews

Spacious suite with private entrance, parking spot

Spacious suite on the third floor of a Victorian home. Private entrance. Off-street parking for one car. Short walk to Boston express bus and other bus lines to Fenway, downtown, Cambridge and other areas. Less than two miles from Boston College. Seven miles from the center of Boston.

Vacation rentals for every style

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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

An open layout kitchen and dining area is displayed, featuring warm wooden cabinetry and a granite countertop. A dining table with four chairs is complemented by a small sofa. The floor showcases polished hardwood, and a large window allows natural light to brighten the space.

Condo in Longwood

4.65 out of 5 average rating, 354 reviews

Modern, Cozy 2 Bedroom in Brookline

Apartment in West Roxbury

A compact kitchenette features a vibrant red refrigerator alongside a small microwave and sink. Modern cabinetry provides storage for dishes and kitchen essentials, while decorative items add a touch of character to the space.

4.96 out of 5 average rating, 28 reviews

Cozy studio near-Train&Bus, safe area in Boston

A well-appointed studio features a spacious bed with a light gray blanket, complemented by decorative pillows. A vibrant piece of artwork adorns the wall above, while natural light streams through the window. A closet and modern furnishings enhance the inviting atmosphere.

Loft in Coolidge Corner

4.75 out of 5 average rating, 248 reviews

Steps to the Green Line & Minutes from Boston!

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

A spacious bedroom is illuminated by natural light from large windows. A king-size bed with neatly arranged linens is centered in the room. An office area with a desk is positioned near the window, and two bedside lamps provide additional lighting beside the bed.

4.96 out of 5 average rating, 23 reviews

①min>Coolidge | King Bed|Full Kitchen|Laundry

4.95 out of 5 average rating, 21 reviews

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.

Townhouse in Brookline

Sunlit Brookline Victorian.

A cozy living area is furnished with a fabric sofa, accent chairs, and decorative pillows. A small wooden stool and a rectangular ottoman complement the seating. A flat-screen television is mounted on the wall, while light-colored curtains frame a window, enhancing the inviting environment.

5 out of 5 average rating, 16 reviews

1 FREE parking spot, Coolidge Corner 1 bed