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Brookline, MA vacation rentals
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Best Vacation rentals and Airbnb offers in Brookline, MA

Choose the Right Family-Friendly Vacation Rentals in Brookline, MA

The right family vacation rental in Brookline, MA makes all the difference, keeping you close to top city attractions.

Duplex Rooftop Near Mit/kendall/harvard With 2 Free Parking! - Brookline, MA
10 3 reviews
Brookline, MA
12/22 – 01/02
$906/nighttotal: $9966 (11 )

Duplex Rooftop Near Mit/kendall/harvard With 2 Free Parking!

3 2
apartment , Cambridge
This 3-bedroom, 2-bathroom apartment is located in Cambridge's Wellington-Harrington district, offering easy access to major squares, a 12-minute walk to Kendall Square and MIT, and a 4-minute drive to Harvard Square.
This family-friendly rental accommodates up to 9 guests and features a private outdoor terrace with a fire pit, a fully equipped kitchen with a lobster pot, and in-unit laundry, perfect for exploring the area.
Luxe 3br Apartment At Mit Harvard With Free Parking - Brookline, MA
8.6 6 reviews
Brookline, MA
12/22 – 01/02
$1044/nighttotal: $11484 (11 )

Luxe 3br Apartment At Mit Harvard With Free Parking

3 2
apartment , Cambridge
This Cambridge apartment is conveniently located within a short walk of Inman Square, Central Square Theatre, and MIT, offering easy access to the city's vibrant cultural scene. The apartment consistently receives excellent ratings for cleanliness, location, and overall user experience.
The 3-bedroom apartment provides 900 square feet of space, comfortably accommodating up to 6 guests. Amenities include free Wi-Fi, parking, a fully equipped kitchen with a dishwasher, air conditioning, a flat-screen TV with streaming services, and a Wii U, ensuring a comfortable and enjoyable stay.
Comforts Of Your Home In Tranquility By Harvard/mit - Brookline, MA
10 6 reviews
Brookline, MA
12/22 – 01/02
$696/nighttotal: $7656 (11 )

Comforts Of Your Home In Tranquility By Harvard/mit

3 2
apartment , Cambridge
This Mid-Cambridge apartment rental is conveniently located near Harvard Square, offering easy access to Harvard University and its surrounding attractions.
This 2,060-square-foot unit sleeps eight guests comfortably in four bedrooms (three queen, two XL twin beds) and includes two bathrooms, a full kitchen with dishwasher, in-unit laundry, a private porch, free Wi-Fi, and parking.
Huge Classy 3br Apt W/parking, Sleeps 7 - Brookline, MA
9.2 81 reviews
Brookline, MA
07/13 – 07/14
$505/nightfor 1 night

Huge Classy 3br Apt W/parking, Sleeps 7

1 5
apartment , Cambridge
This Cambridge apartment rental is located in a quiet, park-filled neighborhood near Harvard University, MIT, the Charles River, and Boston University, providing easy access to the Green and Red lines of the MBTA subway and a short walk to Central Square.
The spacious, architect-designed two-level unit features four bedrooms, two bathrooms, in-unit laundry, on-site parking, and a private porch overlooking a garden, comfortably accommodating seven guests with amenities including a refrigerator, freezer, microwave, and dishwasher.

Best Brookline, MA vacation rentals with parking

World Cup Group Stay 5br Sleeps 16 Near Train Downtown\n - Brookline, MA
9.4 381 reviews
Brookline, MA
06/25 – 06/28
$1003/nighttotal: $3009 (3 )

World Cup Group Stay 5br Sleeps 16 Near Train Downtown\n

3 7
apartment , Boston
This house is located in Dorchester, a residential neighborhood in Boston, within a 3-mile radius of the University of Massachusetts Boston, Northeastern University, and the Boston Museum of Fine Arts. Guests have consistently rated the house excellent for cleanliness, location, and overall experience.
The house has 5 bedrooms, making it suitable for larger families or groups. Amenities include free Wi-Fi, a fully equipped kitchen, a terrace, a garden, a spa, a restaurant, and parking.
1 Free Parking Spot, Coolidge Corner 1 Bed - Brookline, MA
Brookline, MA
12/22 – 01/02
$268/nighttotal: $2948 (11 )

1 Free Parking Spot, Coolidge Corner 1 Bed

1 2
apartment , Brookline
This pet-friendly one-bedroom flat in North Brookline offers a private apartment experience, located one block from the T for convenient access to Fenway Park, Kenmore Square, and Back Bay, with exceptional walkability to Coolidge Corner's markets, restaurants, and shops.
This Brookline apartment includes free parking, a full kitchen with a fridge, microwave, and dishwasher, air conditioning, and a desk for remote work, accommodating up to two guests with an 11:00 AM check-out.
Spacious Home ~Families & Groups~ Parking~backyard - Brookline, MA
10 134 reviews
Brookline, MA
07/13 – 07/14
$929/nightfor 1 night

Spacious Home ~Families & Groups~ Parking~backyard

1 5
apartment , Boston
This spacious Boston Airbnb, located in a quiet neighborhood approximately 2-3 miles from Northeastern University and Fenway Park, offers easy access to major attractions.
This 3000-square-foot historic home features 5 bedrooms, 2 bathrooms, sleeps up to 12 guests, includes a fully equipped kitchen with two ovens, a fenced backyard, on and off-street parking for two cars, and modern amenities like smart TVs and laundry facilities.
Brand-new Spacious 4 Bedroom Home, Minutes From Train Station, Free St Parking - Brookline, MA
8.6 19 reviews
Brookline, MA
06/25 – 06/28
$983/nighttotal: $2949 (3 )

Brand-new Spacious 4 Bedroom Home, Minutes From Train Station, Free St Parking

4 7
apartment , Boston
This Dorchester, Boston home is located 0.6 miles from Franklin Park Zoo and within 3 miles of the University of Massachusetts Boston and Boston Medical Center.
This 4-bedroom, 3-bathroom house sleeps 10 guests and features a fully equipped kitchen, Smart TV, and free parking; enjoy easy access to public transportation.

Frequently Asked Questions about vacation rentals in Brookline, MA

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

    The Brookline Recreation Department offers a wide range of family-friendly activities, including the Brookline Teen Center, the Brookline Community Center, and the Brookline Public Library. The Larz Anderson Park is also a great place for families, with its large playground, picnic areas, and walking trails.
  • What are the best Airbnb and vacation rentals in Brookline, MA?

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

    The best time to book a vacation rental in Brookline is during the shoulder seasons, from April to May and September to October, when the weather is still pleasant but the crowds are smaller. Prices are generally lower during these months, and you'll have a better chance of finding availability.
  • What are the most popular Airbnbs in Brookline, MA?

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

    The Brookline Farmers Market, held every Sunday from June to October, is a great place to sample local produce and crafts. The Brookline Arts Center hosts a variety of art exhibitions and events throughout the year. And don't miss the annual Brookline Town Meeting, a unique event where residents gather to discuss and vote on town issues.
  • What are the best vacation rentals with a pool in Brookline, MA?

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

    Take a stroll through the beautiful Larz Anderson Park, which is free to enter. Visit the Brookline Public Library, which offers free events and programs. And explore the shops and restaurants in Coolidge Corner, which are generally more affordable than those in neighboring Boston.
  • What are the best rentals for families and kids in Brookline, MA?

  • 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 restaurant that has been serving local fare since the 18th century. Another local favorite is The Fireplace, which features a seasonal menu with fresh, locally sourced ingredients.
  • 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 walking or cycling routes in Brookline, MA?

    The Emerald Necklace, a chain of parks designed by Frederick Law Olmsted, runs through Brookline and offers scenic walking and cycling paths. The Muddy River, which flows through the Emerald Necklace, is also a popular spot for walking and biking.
  • Are there pet-friendly attractions in Brookline, MA?

    The Larz Anderson Park is a great place to bring your dog for a walk or a picnic. Many of the restaurants in Coolidge Corner have outdoor seating that is pet-friendly. And the Brookline Public Library hosts occasional dog-friendly events.
  • What are the benefits of choosing a vacation rental in Brookline, MA?

    Vacation rentals often offer more space and privacy than hotel rooms. They are also a great option for families or groups of friends, as they can accommodate larger parties. And many rentals allow pets, making them a good choice for travelers with furry companions.
  • What are the top sports attractions and facilities in Brookline, MA?

    The Brookline Recreation Department offers a variety of sports facilities, including the Brookline High School athletic fields, the Brookline Community Center, and the Brookline Public Library. The Larz Anderson Park also has a large athletic field that is used for a variety of sports.

Destinations nearby

Guest-Favorite Vacation Rentals with a Terrace in Brookline, MA

Start your morning right with a vacation rental in Brookline, MA featuring a private balcony and stunning views.

Modern Boston Condo | Near T - Brookline, MA
10 3 reviews
Brookline, MA
12/22 – 01/02
$1009/nighttotal: $11099 (11 )

Modern Boston Condo | Near T

5 2
apartment , Boston
This Jamaica Plain rental is a 5-bedroom, 2-bathroom apartment conveniently located a 10-12 minute walk from the Forest Hills MBTA Orange Line station, providing easy access to downtown Boston and Franklin Park.
The professionally designed, open-concept unit sleeps up to 12 guests and includes a kitchen with a fridge, microwave, and dishwasher, plus keyless entry, high-speed internet, and a terrace/balcony; on-street parking is available (fees apply).
Vintage 5br Apt In Boston With Free Parking - Brookline, MA
9.7 3 reviews
Brookline, MA
12/22 – 01/02
$824/nighttotal: $9064 (11 )

Vintage 5br Apt In Boston With Free Parking

5 2
apartment , Boston
This spacious 5-bedroom dwelling is located in Boston, offering convenient access to Harvard University, Harvard Square, and Central Square Theatre, all within approximately 2.5 miles, and John F. Kennedy Park and Brattle Theatre are about 2 miles away.
This air-conditioned unit spans 1800 square feet and accommodates up to 22 guests, featuring a fully equipped kitchen with a dishwasher, free WiFi, and private parking, making it ideal for families and groups visiting Boston.
Cozy&spacious 7br Home In Malden W Free Parking - Brookline, MA
Brookline, MA
06/25 – 06/28
$1305/nighttotal: $3915 (3 )

Cozy&spacious 7br Home In Malden W Free Parking

1 7
house , Malden
This Malden house offers convenient access to Cambridge College (3.4 miles) and Boston attractions like TD Garden and Boston North Station (both 4.8 miles), with Logan Airport 4.3 miles away.
This spacious 7-bedroom home provides accommodation for up to 27 guests, featuring complimentary private parking, free Wi-Fi, a fully equipped kitchen, and a balcony.
4br 3bath Harvard Mit Home - Brookline, MA
Brookline, MA
12/22 – 01/02
$1317/nighttotal: $14487 (11 )

4br 3bath Harvard Mit Home

4 2
apartment , Cambridge
This Cambridge apartment rental is centrally located, a short walk from Central Square and Inman Square, and within a mile of Harvard Square and Harvard University.
This spacious 1,292-square-foot residence boasts two bedrooms, three bathrooms, and accommodates up to 27 guests, featuring a fully equipped kitchen, in-unit laundry, free Wi-Fi, a balcony, and parking.

Best Brookline, MA vacation rentals with air conditioning

Newly Renovated 2bed, 2bath Private Apartment, Minutes From Boston. - Brookline, MA
8.7 152 reviews
Brookline, MA
12/22 – 01/02
$197/nighttotal: $2167 (11 )

Newly Renovated 2bed, 2bath Private Apartment, Minutes From Boston.

2 2
apartment , Brookline
This newly renovated Brookline apartment boasts a prime location near Boston University (2.2 miles), the Museum of Fine Arts (2.5 miles), and Fenway Park (1.8 miles), offering easy access to Boston's attractions.
This 2-bedroom, 2-bathroom unit provides 2690 square feet of space, comfortably accommodating up to 4 guests and featuring in-unit laundry, free Wi-Fi, and a fully equipped kitchen with a microwave and refrigerator.
Stylish Studio On Newbury St, This Is Boston! #12 - Brookline, MA
9.2 311 reviews
Brookline, MA
12/22 – 01/02
$234/nighttotal: $2574 (11 )

Stylish Studio On Newbury St, This Is Boston! #12

1 2
studio , Boston
The Stylish Studio is located on Newbury Street in Back Bay, just a short walk from Boston's famous Public Garden, Museum of Fine Arts, and Fenway Park. This studio apartment has received excellent ratings for location, cleanliness, and overall experience.
The studio is a comfortable and modern space with enough room for two guests. It features a fully equipped kitchenette, a bathroom with a walk-in shower, and free WiFi, ensuring a convenient and comfortable stay.
Coolidge Corner-1st Floor-close To The Subway! - Brookline, MA
10 39 reviews
Brookline, MA
10/11 – 10/15
$353/nighttotal: $1412 (4 )

Coolidge Corner-1st Floor-close To The Subway!

1 2
apartment , Brookline
This Brookline studio apartment offers prime access to Boston University, located a 7-minute walk away, and is just a 3-minute walk to Coolidge Corner and the T subway for convenient city exploration.
This accommodation features a full kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, and on-site laundry facilities, accommodating up to 2 guests.
Beautiful Mission Hill 1bedroom - Brookline, MA
9.3 3 reviews
Brookline, MA
12/22 – 01/02
$169/nighttotal: $1859 (11 )

Beautiful Mission Hill 1bedroom

1 2
apartment , Boston
This Mission Hill apartment is located 1.6 miles from Fenway Park and a 14-minute walk from the Boston Museum of Fine Arts.
This 540 square foot residence offers one bedroom and one bathroom, accommodating up to three guests with a fully equipped kitchen, in-unit laundry, and air conditioning.
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