Holiday rentals in Brookline

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Top-rated holiday rentals in Brookline

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Top guest favourite
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.
Guest suite in Jamaica Plain
4.92 out of 5 average rating, 247 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 w/ sink. No stove or cooking. DO NOT request >6 mos ahead. Insta-Book when calendar opens

Guest favourite
The spacious studio features a wooden sleigh bed with a patterned comforter. A cozy seating area includes two modern chairs and a small table near a large window draped with light-colored curtains. An ornate mirror stands against a wall, reflecting the warm wood tones in the room.
Flat in Coolidge Corner
4.83 out of 5 average rating, 115 reviews

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

Top guest favourite
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.
Flat in Coolidge Corner
4.96 out of 5 average rating, 53 reviews

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!

Top guest favourite
A lush garden filled with various plants and trees is viewed, with sunlight filtering through the branches. An assortment of colorful items can be seen among the greenery, creating a vibrant and natural environment. Nearby buildings are visible, set back from the garden.
Home in Jamaica Plain
4.89 out of 5 average rating, 336 reviews

Treetop Haven in the City

This is a sweet, cozy space that is not fancy but homey. You will have everything you need for a comfortable stay including a complete kitchen with everything you will need to make your own meals. We are conveniently located, near the subway and buses, supermarkets, restaurants, and coffee shops. We are within two blocks of the jewel of the Emerald Necklace, Jamaica Pond, and other green spaces. Read our reviews so you can see what previous guests have loved about Treetop Haven.

Top guest favourite
A cozy living area is presented with a comfortable gray sofa and a dark wooden coffee table. A small dining table with two chairs is positioned near the patio doors, which are flanked by light curtains. A patterned area rug adds warmth to the hardwood floor.
Flat in Newton
4.92 out of 5 average rating, 386 reviews

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

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.
Apartment in Brookline
4.85 out of 5 average rating, 253 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.

Top guest favourite
Flat in Coolidge Corner
4.95 out of 5 average rating, 292 reviews

Luxury 2B1B Apt. One Free Parking Spot

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. Pets friendly with extra charge $100/pet/Stay. Our places are professionally cleaned & sanitized.

Top guest favourite
A cozy outdoor patio area is framed by a wooden fence and surrounded by greenery. Vibrant yellow chairs and a matching table are positioned on brick pavers, inviting relaxation. The natural setting includes stones and plants, creating a tranquil garden space.
Guest suite in Jamaica Plain
4.89 out of 5 average rating, 142 reviews

Urban Guest Suite

Come stay at the guest suite in our quirky, historic home in Jamaica Plain, one of Boston's most diverse and exciting areas. The suite is on the ground floor with a private patio and private entrance. Guests enjoy their own private space with a bathroom, queen size bed, and work area. Located 2 blocks away from the Stony Brook Orange line “T” and a 10 minute walk to local restaurants and super markets.

Top guest favourite
Flat in Brookline
4.84 out of 5 average rating, 31 reviews

The Garden Apartment

Conveniently located in the heart of Brookline. Private entrance. Lovely garden with outdoor furniture in a quiet neighborhood. Kitchenette with refrigerator, microwave, washer and dryer. TV, Wifi, and private bath. Parking available. Walking distance to shops and restaurants. Easy access to downtown Boston. Two Green Line T-stops are each 0.4 miles away. Maximum two people.

Top guest favourite
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.
Apartment in Brookline Village
4.97 out of 5 average rating, 115 reviews

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.

Top guest favourite
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.
Apartment in Jamaica Plain
4.89 out of 5 average rating, 581 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).

Guest favourite
Guest suite in Brookline
4.88 out of 5 average rating, 273 reviews

Brookline Home with a Garden

The 1 bedroom apartment is in the basement of our single family home. There is free parking. It is equipped with its own entrance, bathroom, kitchenette, porch, and garden. There is 1 queen bed in the bedroom and 1 full bed in the studio living area. ***No kids under the age of 3 the family lives upstairs, there will be some noise,

Popular amenities for Brookline holiday rentals

When is the best time to visit Brookline?

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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

Destinations to explore