Holiday Rentals in Brookline, MA

1019 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Brookline, MA holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Holiday rentals and Airbnb offers in Brookline, MA

Best family friendly Brookline, MA holiday rentals

Among the 1019 accommodations in Brookline, MA, here are the 4 best family friendly rentals

Boston Landing Stays - Brookline, MA
8.1 115 reviews

Boston Landing Stays

apartment, Boston
This Boston apartment, situated approximately 1.6km from Harvard Square and 3.2km from the Brattle Theatre, offers convenient access to Cambridge and Boston city centre.
The 75 square metre self-catering flat features a fully equipped kitchen, private patio, free Wi-Fi, one bathroom, and parking, sleeping up to [Number of guests needs to be specified, e.g., four people comfortably].
Upscale 1br Mit Harvard Wifi Gym W D Parking! - Brookline, MA
No reviews

Upscale 1br Mit Harvard Wifi Gym W D Parking!

apartment, Cambridge
This two-bedroom Cambridge apartment, situated in Central Square, offers easy access to Kendall Square, MIT, Harvard Square, and Downtown Boston, all within a 10-15 minute journey.
The 60 square metre flat includes a fully equipped kitchen, in-unit laundry, a garden, parking, and accommodates up to five guests, with access to a fitness centre, business centre, and club room.
3br2bth Parking, Cambridge/boston, W/d, Subway,a/c - Brookline, MA
9.6 19 reviews

3br2bth Parking, Cambridge/boston, W/d, Subway,a/c

apartment, Somerville
This three-bedroom Cambridge dwelling, situated in Ward Two, is less than 1.6km from the Cambridgeside Galleria and Museum of Science, and under 3.2km from MIT and Harvard University, offering easy access to public transport.
The 102 square metre property boasts two bathrooms, in-unit laundry, free Wi-Fi, a garden, parking, and sleeps up to seven guests, making it ideal for families or groups visiting Cambridge.
Brighton 2br Loft | T Access, Near Bu And Bc - Brookline, MA
9.8 71 reviews

Brighton 2br Loft | T Access, Near Bu And Bc

apartment, Boston
This Brighton loft apartment, situated in a quiet street near a park and close to several universities in Boston, Massachusetts, offers a peaceful retreat.
The two-bedroom, one-bathroom flat sleeps four guests and features a fully equipped kitchen (fridge, freezer, microwave), air conditioning, and Wi-Fi; limited parking is available, and access is via two flights of stairs.

Best Brookline, MA holiday rentals with parking

Harvard/mit 2br/2ba + 2 Parking By Central Sq - Brookline, MA
9.4 31 reviews

Harvard/mit 2br/2ba + 2 Parking By Central Sq

apartment, Cambridge
This two-bedroom apartment is located in the Port district of Cambridge, just a short walk from Central Square and Inman Square, and within easy reach of Harvard University, MIT, and the Red Line T. It has consistently received excellent reviews from previous guests.
The apartment offers a spacious open-plan living area with a private porch, catering to a maximum of five guests. It is fully equipped with a kitchen, washer/dryer, high-speed Wi-Fi, and two parking spaces, and features a Jacuzzi tub and a private deck with outdoor seating.
Min>coolidge: Full Kitchen- 2 - Brookline, MA
No reviews

Min>coolidge: Full Kitchen- 2

apartment, Brookline
This Brookline flat is located in the Coolidge Corner South Side district, 7 minutes' walk from the Coolidge Corner Theatre and 6 minutes' walk from the Coolidge Corner streetcar stop, with Fenway Park a 4-minute drive away.
This 2-bedroom, 1-bathroom apartment accommodates up to 4 guests and offers a fully equipped kitchen, Wi-Fi, air conditioning, and on-site laundry facilities.
Central Space To Balance Life Work Play 7 Sleeps - Brookline, MA
9.4 18 reviews

Central Space To Balance Life Work Play 7 Sleeps

apartment, Cambridge
This Cambridge apartment, situated in a central location, is a 3-minute walk from the Central Square Theatre, an 11-minute walk from the Massachusetts Institute of Technology (MIT), and close to Inman Square and the University of Cambridge.
This 93 square metre (1000 square foot) self-catering property features two bedrooms sleeping up to seven guests, two bathrooms, a fully equipped kitchen, in-unit laundry, free Wi-Fi, on-site fitness centre, garden, and parking, making it ideal for groups visiting Cambridge.
3br  Cozy Boston Condo, Near T - Brookline, MA
9.8 89 reviews

3br Cozy Boston Condo, Near T

apartment, Boston
This Jamaica Plain apartment, a short walk from the 'T' subway providing easy access to Boston's attractions, offers a convenient base for exploring the city.
The three-bedroom, two-bathroom property boasts an open-plan layout, sleeping up to seven guests comfortably and includes amenities such as a fully equipped kitchen, high-speed internet, and off-street parking – a valuable asset in Boston.

Frequently asked questions about holiday rentals in Brookline, MA

  • What should a first-time visitor not miss in Brookline, MA?

    Brookline has a lot to offer, but for a first-timer, you can't go wrong with a visit to the iconic Coolidge Corner Theatre, a historic cinema with a charming art deco feel. Take a stroll through the picturesque Larz Anderson Park, with its beautiful gardens and historic mansion. And if you're a fan of art, the Brookline Arts Center is a must-see, showcasing local talent and hosting engaging exhibitions.
  • What are the best Airbnb and vacation rentals in Brookline, MA?

  • Which neighborhood in Brookline, MA should you consider for a vacation rental?

    Coolidge Corner is a popular choice for visitors, with its vibrant atmosphere, independent shops, and restaurants. It's close to the Green Line T station, making it easy to explore Boston. For a more residential feel, consider the peaceful and family-friendly neighbourhood of Chestnut Hill, known for its tree-lined streets and proximity to the beautiful Chestnut Hill Reservoir.
  • What are the most popular Airbnbs in Brookline, MA?

  • What are the top family-friendly attractions in Brookline, MA?

    The Larz Anderson Park is perfect for families, with its sprawling grounds, playground, and the Larz Anderson Auto Museum. The Brookline Public Library offers a variety of children's programmes and events, and the Brookline Recreation Department organises numerous activities for families throughout the year.
  • What are the best vacation rentals with a pool in Brookline, MA?

  • When is the best time to book a vacation rental in Brookline, MA?

    To avoid the peak season crowds and higher prices, consider booking your vacation rental in the shoulder seasons, such as spring (April-May) or autumn (September-October). However, if you're looking for a lively atmosphere, summer (June-August) offers many outdoor events and festivals.
  • What are the best rentals for families and kids in Brookline, MA?

  • What events or festivals should visitors check out in and around Brookline, MA?

    The annual Brookline Open Studios is a great opportunity to explore the local art scene, while the Brookline Farmers Market offers fresh produce and local crafts. In nearby Boston, you can catch the Boston Pops Fireworks Spectacular on the Fourth of July or the Boston Marathon in April, a truly iconic event.
  • What are the best rentals or Airbnbs with a jacuzzi in Brookline, MA?

    The best vacation rentals or Airbnb with a jacuzzi in Brookline, MA are Ultraluxe Apt In Boston Brownstone In Prime Area, Beautiful Clean Bright Corner Unit and Walking To Fenway Sunny Perfect Home.

  • What are the best budget-friendly activities in Brookline, MA?

    Brookline has many free activities, including a walk around the picturesque Chestnut Hill Reservoir, a visit to the Brookline Public Library, or enjoying the outdoor concerts and events at Larz Anderson Park. The Brookline Farmers Market is also a great way to experience local culture without breaking the bank.
  • What are the best restaurants with local dishes in Brookline, MA?

    For a taste of New England, try the classic clam chowder at The Publick House, a historic tavern with a warm atmosphere. If you're looking for something more contemporary, The Blue Room offers a modern take on American cuisine with fresh, seasonal ingredients. And for a casual bite, The Spot serves up delicious sandwiches and salads.
  • What are the best walking or cycling routes in Brookline, MA?

    A walk or cycle along the Emerald Necklace, a chain of parks connecting Brookline to Boston, is a great way to enjoy the natural beauty of the area. The paved path around the Chestnut Hill Reservoir offers scenic views and is ideal for a leisurely stroll or bike ride. For a more challenging ride, try the paved bike path along the Charles River, which stretches for miles.
  • Are there pet-friendly attractions in Brookline, MA?

    Larz Anderson Park is a great place to take your furry friend for a walk, with its large open spaces and walking trails. Many of the restaurants in Coolidge Corner also have outdoor seating where you can enjoy a meal with your pet.
  • What are the benefits of choosing a vacation rental in Brookline, MA?

    Vacation rentals offer more space and privacy compared to hotels, making them ideal for families or groups. They often come with kitchen facilities, allowing you to prepare your own meals and save on dining costs. Additionally, they provide a more authentic experience, allowing you to live like a local and enjoy the neighbourhood.
  • What are the top sports attractions and facilities in Brookline, MA?

    Brookline is home to the iconic Brookline Country Club, which has hosted numerous prestigious golf tournaments, including the US Open. The town also boasts several public parks with sports facilities, including tennis courts, basketball courts, and baseball fields. For a more casual experience, the Brookline Recreation Department offers a variety of sports programmes and activities for all ages.

Popular destinations

Best Brookline, MA holiday rentals with a balcony

The Only 4 Bedroom Apartment W/ Roofdeck In Boston!  8min From Fenway Park, Close To Universities! - Brookline, MA
9.6 4 reviews

The Only 4 Bedroom Apartment W/ Roofdeck In Boston! 8min From Fenway Park, Close To Universities!

apartment, Boston
This four-bedroom flat is located in Boston's Fenway district, a 5-minute walk from Fenway Park, with Back Bay, Brookline, The Fens, and the Charles River Esplanade all within an 8-minute stroll.
This top-floor apartment in a historic 120-year-old building accommodates up to eight guests and features a furnished roof deck offering city views from May to October, alongside a kitchen with a fridge, microwave, and dishwasher, and air conditioning.
The Harvard Loft With Game Room And Free Parking Near Harvard Square - Brookline, MA
No reviews

The Harvard Loft With Game Room And Free Parking Near Harvard Square

house, Cambridge
The Harvard Loft offers a prime Old Cambridge location, a 10-minute walk to Harvard University and an 11-minute walk to Harvard Square, with John F. Kennedy Park 1.2 kilometres away.
This spacious 4-bedroom property provides accommodation for 12 guests, featuring air conditioning, free Wi-Fi, a fully equipped kitchen with a dishwasher and oven, and an in-unit washing machine, all spread across 1000 square meters.
Arboretum Retreat City Of Boston - Brookline, MA
9.4 8 reviews

Arboretum Retreat City Of Boston

apartment, Boston
This renovated basement flat in Roslindale, Boston, offers easy access to Boston's cultural attractions such as the Museum of Fine Arts and Berklee College of Music, though precise distances are not specified.
The two-bedroom, one-bathroom apartment sleeps four guests and features a well-equipped kitchen with new appliances, a spa-like bathroom with a double-head shower, and on-demand cleaning services; six wide stairs provide easy access.
Boston Historical Urban Oasis - Brookline, MA
8.8 10 reviews

Boston Historical Urban Oasis

apartment, Boston
This seven-bedroom apartment in Allston is just a two-minute walk from the Green Line train station, offering easy access to downtown Boston, Harvard, and MIT. The property has a very good user rating and is ideal for groups or families visiting the city.
The apartment is fully furnished and spacious, with two full bathrooms and one half bathroom, accommodating up to ten guests. Guests can enjoy a range of amenities, including a garden, laundry facilities, parking, and a kitchen equipped with a fridge, microwave oven, and dishwasher.

Best Brookline, MA holiday rentals with air conditioning

3br2bth Parking Cambridge Boston W&d Subway Ac - Brookline, MA
9.8 16 reviews

3br2bth Parking Cambridge Boston W&d Subway Ac

house, Somerville
This Somerville holiday home is situated near Inman Square, approximately 1.9km from the Central Square Theatre, 2.3km from the Massachusetts Institute of Technology (MIT), and a short distance from Cambridge College and the Peabody Museum.
The 102 square metre property offers three bedrooms, two bathrooms, sleeps thirteen guests, and includes free Wi-Fi, private parking, and a fully equipped kitchen with a dishwasher.
Upscale Penthouse Near Mit Harvard Central Square - Brookline, MA
8.5 9 reviews

Upscale Penthouse Near Mit Harvard Central Square

apartment, Cambridge
This one-bedroom apartment is located in Cambridge, a short walk from Central Square and within easy reach of both Harvard University and the Massachusetts Institute of Technology.
The 70 square metre flat is equipped with a fully-equipped kitchen, a washing machine, a TV, and a garden, and it can accommodate up to 9 guests.
Nice 2bd/1.5ba Near Bu D53e - Brookline, MA
10 1 review

Nice 2bd/1.5ba Near Bu D53e

apartment, Brookline
This three-bedroom apartment in North Brookline is a short walk from Boston University and the Amory Green Line station, providing easy access to major hospitals such as Dana-Farber Cancer Institute and Beth Israel Deaconess Medical Center.
The 84-square-metre (904 square feet) self-catering flat features two bathrooms, a king-size bed and two queen-size beds, accommodating up to four guests, and includes a fully equipped kitchen with a fridge, microwave, and dishwasher, plus in-building laundry facilities (charges apply).
Historic-esque House Modernized - Brookline, MA
9.8 375 reviews

Historic-esque House Modernized

apartment, Boston
This spacious four-bedroom apartment is located in the Brighton neighbourhood of Boston, just a short walk from Brighton Centre and a five-mile drive from the city centre. The property has received excellent ratings for its location, cleanliness and overall experience.
The apartment spans 205 square metres and comfortably accommodates up to 12 guests. The property offers a range of amenities including a private garden, a terrace, a spa, parking, and a fully equipped kitchen.
©2026 cozycozy.com