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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.

Charming Boston Single Fam Home Near Commuter Rail - Brookline, MA
9.9 44 reviews
Brookline, MA
12/22 – 01/02
$307/nighttotal: $3377 (11 )

Charming Boston Single Fam Home Near Commuter Rail

1 2
apartment , Boston
This West Roxbury apartment rental is conveniently located near the commuter rail, Longwood Medical Area, and Centre Street's shops and restaurants.
The three-bedroom, one-bathroom unit features a finished basement gym (Peloton and weights), a fenced backyard, and accommodates up to five guests with a king, queen, and twin beds; a well-equipped kitchen with island seating and dining area completes this family-friendly Boston lodging option.
Luxe 3bd Allston - Brookline, MA
Brookline, MA
07/13 – 07/14
$1156/nightfor 1 night

Luxe 3bd Allston

3 5
apartment , Boston
This 3-bedroom, 2-bathroom rental unit is located in Boston's Allston neighborhood, 1.6 miles from John F. Kennedy Park and 2 miles from Harvard Square.
This 1490 square foot residence accommodates up to 14 guests and features air conditioning, free WiFi, a fully equipped kitchen with a dishwasher, and complimentary private parking.
2 Bdrm Apt W/ Tower In Jp Victorian - Brookline, MA
9.9 530 reviews
Brookline, MA
12/22 – 01/02
$218/nighttotal: $2398 (11 )

2 Bdrm Apt W/ Tower In Jp Victorian

2 2
apartment , Boston
This apartment in Boston is a family-friendly accommodation with an excellent user, location, and cleanliness rating. It is ideal for 4 guests and offers a fully equipped kitchen, air conditioning, a garden, and parking.
The apartment is conveniently located in Boston, within walking distance of many landmarks and attractions. Guests can enjoy the city's vibrant atmosphere and explore its rich history and culture.
Skyrise Two Stories - Centrally Located - Brookline, MA
9.5 194 reviews
Brookline, MA
07/13 – 07/14
$529/nightfor 1 night

Skyrise Two Stories - Centrally Located

1 5
apartment , Brookline
This Brookline apartment is conveniently located within a mile of Longwood Medical Area, Brigham and Women's Hospital, and Children's Hospital Boston, making it ideal for families visiting patients or medical professionals working in the area. The apartment has excellent user, location, and cleanliness ratings, making it a comfortable and enjoyable place to stay.
The apartment offers 1,500 square feet of space with 4 bedrooms and 2 bathrooms. Guests can enjoy a fully equipped kitchen, a garden, free WiFi, and a Smart TV, providing everything needed for a comfortable and convenient stay.

Best Brookline, MA vacation rentals with parking

2min->coolidge&greent/king Bed/full Kitchen/arcade - Brookline, MA
Brookline, MA
12/22 – 01/02
$503/nighttotal: $5533 (11 )

2min->coolidge&greent/king Bed/full Kitchen/arcade

2 2
apartment , Brookline
This Brookline apartment rental is located in Coolidge Corner's South Side, a three-minute walk from the Green Line T station providing easy access to Downtown Boston, Fenway Park, and the Longwood Medical Area.
The two-bedroom unit features a 65-inch 4K Smart TV, a fully equipped kitchen, a Galaga arcade game in the second bedroom, and accommodates up to five guests, with daily parking available for $30 at a nearby lot.
4br 3bath Harvard Mit Home - Brookline, MA
Brookline, MA
08/31 – 09/01
$1473/nightfor 1 night

4br 3bath Harvard Mit Home

4 4
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.
3-bedroom Apt-7b2 20-minuite To Downtown Boston - Brookline, MA
Brookline, MA
07/13 – 07/14
$582/nightfor 1 night

3-bedroom Apt-7b2 20-minuite To Downtown Boston

3 5
apartment , Boston
This 3-bedroom residence in Boston is located 3.6 miles from the Museum of Fine Arts and 6.2 miles from Logan Airport, offering a residential feel with reasonable access to key city attractions.
This 1500 square foot apartment accommodates up to 13 guests with 3 bedrooms and 3 bathrooms, featuring free WiFi, a full kitchen, air conditioning, and private parking, and is situated 20 minutes from downtown Boston.
2 Bedroom Boston Condo In Jamaica Plain With Parking - Brookline, MA
9.7 161 reviews
Brookline, MA
12/22 – 01/02
$326/nighttotal: $3586 (11 )

2 Bedroom Boston Condo In Jamaica Plain With Parking

2 2
apartment , Boston
This Egleston Square Condo is located in Jamaica Plain, a charming neighborhood with easy access to Boston's Orange Line subway, providing quick access to the city center and its attractions. The apartment has excellent user, location, and cleanliness ratings.
This two-bedroom, one-bathroom rental can comfortably accommodate five guests. The condo offers a fully equipped kitchen, a spacious living room with a flat-screen TV, and access to a yard, BBQ, and bicycles for outdoor enjoyment.

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 4 Bed 2.5 Bath Home Near Harvard With Free Parking - Brookline, MA
10 58 reviews
Brookline, MA
08/31 – 09/01
$870/nightfor 1 night

Modern 4 Bed 2.5 Bath Home Near Harvard With Free Parking

4 4
apartment , Boston
This modern condo is located in the Allston neighborhood of Boston, just a short distance from Harvard University and MIT, and a 10-minute drive from downtown Boston and Fenway Park. It has excellent user ratings and is a perfect choice for families or groups looking for a comfortable and convenient stay. This 2,500 square foot home has 4 bedrooms and 3 bathrooms, comfortably accommodating up to 12 guests. The condo offers a fully equipped kitchen, a private backyard patio with a fire pit and BBQ grill, a Jacuzzi, and a washer/dryer, ensuring a comfortable and enjoyable stay.
Harvard/mit: Most Loved By Repeat Guests & Long-term Guests! - Brookline, MA
9.4 3 reviews
Brookline, MA
12/22 – 01/02
$380/nighttotal: $4180 (11 )

Harvard/mit: Most Loved By Repeat Guests & Long-term Guests!

2 2
apartment , Cambridge
This Mid-Cambridge rental is minutes from Harvard Square, providing easy access to Boston via public transportation and proximity to cultural attractions like the Museum of Science and Berklee College of Music.
The 640-square-foot, two-bedroom, one-bathroom apartment features a renovated interior with original wood floors, 15-foot ceilings, a terrace, a garden, parking, and accommodates up to four guests; amenities include a dishwasher, microwave, refrigerator, air conditioning, and internet access.
The Harvard Loft - Brookline, MA
Brookline, MA
12/22 – 01/02
$1212/nighttotal: $13332 (11 )

The Harvard Loft

4 2
house , Cambridge
The Harvard Loft is a spacious vacation home located in Old Cambridge, a 10-minute walk from Harvard University and 11 minutes from Harvard Square, with John F. Kennedy Park 0.9 miles away.
This 10,760 square foot house offers 4 bedrooms, accommodates up to 12 guests, and features a fully equipped kitchen with a dishwasher and oven, in-unit laundry, air conditioning, and free WiFi.
Modern Boston Condo | Near T - Brookline, MA
9.0 2 reviews
Brookline, MA
12/22 – 01/02
$1009/nighttotal: $11099 (11 )

Modern Boston Condo | Near T

5 2
apartment , Boston
This 5-bedroom, 2-bathroom Jamaica Plain apartment is a 10-12 minute walk to the Forest Hills Orange Line station, offering a 15-minute commute to downtown Boston, and is a 5-minute walk to Franklin Park Arboretum.
This rental unit accommodates up to 10 guests with a fully stocked kitchen featuring a fridge, microwave, and dishwasher, plus high-speed internet and air conditioning, and offers a terrace/balcony for enjoying the surroundings.

Best Brookline, MA vacation rentals with air conditioning

Stylish Studio On Newbury Street, #10 - Brookline, MA
9.3 993 reviews
Brookline, MA
12/22 – 01/02
$191/nighttotal: $2101 (11 )

Stylish Studio On Newbury Street, #10

1 2
studio , Boston
This studio apartment is located on Newbury Street in Boston's Back Bay neighborhood, a short walk from Fenway Park and the Massachusetts Institute of Technology, putting you right in the heart of the city's cultural scene. Guests have consistently rated the studio excellent for its location, cleanliness, and overall experience.
The studio comfortably accommodates two guests and features a fully equipped kitchenette with a microwave and toaster, allowing you to prepare light meals and snacks. Enjoy the convenience of free Wi-Fi, air conditioning, and city views from the studio, making your stay in Boston both comfortable and enjoyable.
2-bedroom Quiet Cambridge, Sleeps Up To 5 - Brookline, MA
9.9 147 reviews
Brookline, MA
08/31 – 09/01
$463/nightfor 1 night

2-bedroom Quiet Cambridge, Sleeps Up To 5

1 4
apartment , Cambridge
This Cambridge apartment rental boasts a central location between Harvard University and the Massachusetts Institute of Technology (MIT), within walking distance of Kendall Square and the Charles River.
The two-bedroom, one-bathroom unit features an open-concept living/dining area, a fully equipped kitchen with dishwasher, a private patio with grill, and off-street parking for one car; it comfortably sleeps five guests with a queen bed, double bed, and inflatable queen-sized air mattress.
Cozy Stay Near Harvard/bu/bc With Parking - Brookline, MA
9.7 447 reviews
Brookline, MA
08/31 – 09/01
$313/nightfor 1 night

Cozy Stay Near Harvard/bu/bc With Parking

1 4
apartment , Boston
This apartment is located in the Allston/Brighton neighborhood, just a short drive from Downtown Boston and popular attractions like Fenway Park, Harvard University, and the Museum of Fine Arts. The apartment consistently receives excellent ratings for cleanliness, location, and user experience.
This comfortable one-bedroom unit sleeps up to six guests and features a fully equipped kitchen, air conditioning, parking, and private entrance. The apartment is near public transportation, making it easy to explore all that Boston has to offer.
Luxury 2br | Free Parking | Harvard/bu | Roku Tv - Brookline, MA
9.8 13 reviews
Brookline, MA
08/31 – 09/01
$507/nightfor 1 night

Luxury 2br | Free Parking | Harvard/bu | Roku Tv

1 4
apartment , Boston
This 2-bedroom, 1-bathroom apartment is located in Boston's Allston neighborhood, approximately 5 miles from Downtown Boston and minutes from Harvard University, Fenway Park, and the Charles River.
This spacious 1000 sq. ft. unit accommodates up to 5 guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning, 400 Mbps Wi-Fi, HDTVs in each room, and on-site parking.
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