Holiday Rentals in Brookline, MA

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Brookline, MA holiday rentals
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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

Central Square 2br Penthouse Near Mit & Harvard To Balance Life, Work Play Sleep 7! - Brookline, MA
No reviews

Central Square 2br Penthouse Near Mit & Harvard To Balance Life, Work Play Sleep 7!

apartment, Cambridge
This two-bedroom Cambridge apartment, ideally located in Central Square, is a five-minute walk from the Central Square underground station and a short drive from Harvard Square and Fenway Park.
The 94 square metre property boasts two bathrooms, sleeps eight guests, and includes amenities such as Wi-Fi, air conditioning, a fireplace, in-unit laundry, and garage parking.
New Spacious 2b2b Apartment, One Free Parking Spot - Brookline, MA
9.9 287 reviews

New Spacious 2b2b Apartment, One Free Parking Spot

apartment, Brookline
This Brookline apartment is ideally located near Coolidge Corner, offering easy access to Boston's T-system and proximity to the Longwood Medical Area, Fenway Park, and Boston University.
The recently renovated two-bedroom, two-bathroom flat sleeps six guests and includes a fully equipped kitchen, free parking, and individual climate control; pet-friendly (surcharge applies).
Vintage 5br Apt In Boston With Free Parking - Brookline, MA
9.7 3 reviews

Vintage 5br Apt In Boston With Free Parking

apartment, Boston
This spacious 5-bedroom flat in Boston offers convenient access to Harvard University and Harvard Square, located approximately 4 kilometres away, with Brattle Theatre and Central Square Theatre also within 4 kilometres.
This substantial property boasts 167 square metres of living space, accommodating up to 22 guests with its five bedrooms and two bathrooms, and includes private parking and a balcony.
Luxe 2br Townhouse | Kendall Sq/mit | Private Entry - Brookline, MA
10 2 reviews

Luxe 2br Townhouse | Kendall Sq/mit | Private Entry

apartment, Cambridge
This luxury 130 square metre flat in East Cambridge offers direct shuttle access to Lechmere Station, placing guests approximately 800 meters from the FIFA World Cup 2026 Fan Zone and a short distance from Harvard Square.
This 2-bedroom, 2-bathroom residence accommodates up to six guests with a fully equipped Chef's Kitchen, spa-like bathrooms, resort-style courtyard with a fire pit and BBQ grill, and executive-ready amenities including 1GB fibre WiFi and a dedicated workspace.

Best Brookline, MA holiday rentals with parking

Upscale 1br Near Mit Harvard With Parking - Brookline, MA
9.0 3 reviews

Upscale 1br Near Mit Harvard With Parking

apartment, Cambridge
This Cambridge apartment, situated near Central Square, offers easy access to MIT, Harvard University, and Inman Square, all within a short walking distance.
The 79 square metre, one-bedroom flat sleeps seven guests and includes a fully equipped kitchen, garden, fitness centre, parking, and free Wi-Fi.
2 Free Parking Spots- In Unit Washer/dryer - Brookline, MA
9.7 98 reviews

2 Free Parking Spots- In Unit Washer/dryer

apartment, Brookline
This Brookline apartment is ideally located just 0.16 kilometres from a T subway station, providing easy access to Boston attractions such as Fenway Park and Kenmore Square.
The one-bedroom flat offers a fully equipped kitchen, in-unit laundry, garage parking, and sleeps four guests comfortably, thanks to a pull-out sofa bed; basic toiletries are provided.
2 Br | 1 Ba  Close To Dwtn & Medical, Free Prkg - Brookline, MA
9.6 286 reviews

2 Br | 1 Ba Close To Dwtn & Medical, Free Prkg

apartment, Boston
This two-bedroom apartment is located in Jamaica Plain, just 8km from downtown Boston and the Longwood Medical area, offering easy access to the city's attractions and amenities. The property has consistently received excellent reviews from guests, highlighting its cleanliness, location, and overall value.
The apartment features a spacious living area and a fully equipped kitchen, comfortably accommodating up to four guests. Guests can enjoy the shared garden, complete with a patio, barbecue, and a friendly dog on the upper floor.
The Drew : Vibrant  Comfortable  W/d  City View - Brookline, MA
9.6 124 reviews

The Drew : Vibrant Comfortable W/d City View

apartment, Boston
This apartment is conveniently located just a 5-minute walk from the T, making it easy to explore Boston College, Harvard, and the city centre, all within a few kilometres. It has received excellent ratings for location, cleanliness, and overall experience.
This comfortable flat sleeps up to four guests and features a separate bedroom with a sliding door, giving the feel of a full one-bedroom apartment. Guests can enjoy luxurious amenities such as a 24/7 concierge, a gym, and a sky lounge with panoramic city views.

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

3br Hotel Alternative - Walk To Kendall Square - Brookline, MA
No reviews

3br Hotel Alternative - Walk To Kendall Square

apartment, Cambridge
This three-bedroom flat is located in Cambridge's Wellington-Harrington district, a short walk from Kendall and Inman Squares, with the Green Line train 965 meters away.
Spanning 84 square meters, this residence accommodates six guests and features a fully equipped kitchen, in-unit laundry, air conditioning with individual room control, a private garden deck, and off-street parking for one vehicle.
Modern/luxury | Steps From Zoo & Golf Course - Brookline, MA
9.8 56 reviews

Modern/luxury | Steps From Zoo & Golf Course

apartment, Boston
This 4-bedroom apartment is located in Roxbury, a neighbourhood in Boston, just 3 km from Fenway Park and 5 km from Faneuil Hall Marketplace, offering a peaceful escape from the city bustle. It has received excellent reviews from previous guests.
The apartment offers ample space for families or groups of friends, comfortably accommodating up to 11 guests. Amenities include a fully equipped kitchen, a 75” 4k TV, high-speed Wi-Fi, a private gym, a terrace, and a garden.
New 9br6bth Parking Mit Harvard Boston Walk To T - Brookline, MA
10 2 reviews

New 9br6bth Parking Mit Harvard Boston Walk To T

apartment, Somerville
This Somerville apartment, situated in Ward Two, offers easy access to Boston via the Union Square T-station, an eight-minute walk away.
This spacious property boasts 2450 square metres of floor area, sleeping up to 23 guests across 10 bedrooms and 6 bathrooms, and includes three kitchens, parking for eight vehicles, and in-unit laundry facilities.
4br Mid-century Glam Retreat | Near T - Brookline, MA
No reviews

4br Mid-century Glam Retreat | Near T

apartment, Boston
This four-bedroom flat in Boston's Jamaica Plain district is a private unit within a triplex, situated 5 minutes on foot from the Franklin Park arboretum and a 15-minute commute from downtown Boston via the Green Street T stop.
This 186 square metre apartment offers accommodation for up to 11 guests, featuring a custom chef's kitchen, a private back porch, air conditioning, internet, and one off-street parking space, with Tempurpedic-quality mattresses and premium linens for comfort.

Best Brookline, MA holiday rentals with air conditioning

The Watkins : Elevated Cozy  W/d  Amenities - Brookline, MA
9.6 117 reviews

The Watkins : Elevated Cozy W/d Amenities

apartment, Boston
This studio apartment is conveniently located just 5km from Boston College and Harvard University, with easy access to public transport via the T, which is a short 5-minute walk away. The surrounding area offers a blend of academic and urban vibes, with plenty of restaurants, shops, and green spaces to explore.
The apartment has one bedroom with a queen-size bed and a fully equipped kitchen, comfortably accommodating up to three guests. Enjoy a range of amenities, including a swimming pool, garden, fitness centre, and parking, as well as access to shared lounges, kitchens, and meeting spaces within the complex.
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.
A Stylish Stay W/ A Queen Bed, Heated Floors.. #31 - Brookline, MA
9.2 540 reviews

A Stylish Stay W/ A Queen Bed, Heated Floors.. #31

apartment, Brookline
This one-bedroom apartment is conveniently located in Brookline, just a short distance from both Fenway Park and Boston University, offering easy access to the vibrant city attractions. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment is perfect for a couple, with its 28 square metres of space and a comfortable queen-sized bed. Guests can enjoy amenities such as a fully equipped kitchen, a washing machine, free Wi-Fi, and heated floors, making for a pleasant and convenient stay.
Coolidge Corner-close To The Subway-free Parking. - Brookline, MA
No reviews

Coolidge Corner-close To The Subway-free Parking.

apartment, Brookline
This 4-bedroom, 2-bathroom flat is situated in Brookline, just a few blocks from the T (subway) and adjacent to Boston University and Coolidge Corner, with quick access to Fenway Park, Kenmore Square, Back Bay, and the Longwood Medical Area.
This pet-friendly apartment accommodates up to 8 guests and includes a kitchen with a fridge, freezer, microwave, and dishwasher, along with air conditioning and a free parking space, offering excellent walkability to Coolidge Corner's shops and restaurants and convenient travel to Boston's major attractions.
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