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

Luxe 3bd Allston - Brookline, MA
No reviews

Luxe 3bd Allston

apartment, Boston
This family-friendly Allston flat is conveniently located 2.6 kilometres from Harvard Square and 2.3 kilometres from Harvard University, with John F. Kennedy Park 1.6 kilometres away and Brattle Theatre 2 kilometres distant.
This spacious 138 square metre apartment offers three bedrooms, two bathrooms, air conditioning, complimentary WiFi, and free private parking, accommodating up to 14 guests with a fully equipped kitchen including a fridge, microwave oven, and dishwasher.
Home-like 4br-3ba Apt | Near Ashmont Station (New) - Brookline, MA
10 21 reviews

Home-like 4br-3ba Apt | Near Ashmont Station (New)

apartment, Boston
This Dorchester apartment, a 7-10 minute walk from Ashmont Red Line station, offers easy access to Boston city centre and is situated approximately 0.8 km from Highway 93.
Sleeping up to 12 guests comfortably in four bedrooms and with three bathrooms, this family-friendly property features a modern open-plan kitchen, living and dining area, private garden, parking, and high-speed internet access.
Chic 3br1.5ba City Stay - Near T + Parking - Brookline, MA
No reviews

Chic 3br1.5ba City Stay - Near T + Parking

apartment, Boston
This 3-bedroom flat in Boston's Dorchester district is a convenient 7-10 minute walk from the Savin Hill T station, providing easy access to the city's attractions.
This family-friendly accommodation offers off-street parking, air conditioning, a kitchen with essential appliances, and a terrace, comfortably sleeping up to 11 guests with its adaptable futon sofas.
Hyatus Luxury Residences Boston Everett Signature Collection - Brookline, MA
9.6 7 reviews

Hyatus Luxury Residences Boston Everett Signature Collection

apartment, Everett
This Everett flat is located 3.6 kilometres from Cambridge College and 5.9 kilometres from North Station and TD Garden, with Boston Logan International Airport a mere 4 kilometres away.
This pet-friendly apartment offers 600 square metres of space for up to 7 guests, featuring a private terrace, bar, barbecue facilities, air conditioning, a fully equipped kitchen with a refrigerator and coffee machine, a communal lounge, a swimming pool, and on-site fitness centre, with free Wi-Fi throughout.

Best Brookline, MA holiday rentals with parking

1 Free Parking Spot Coolidge Corner 1 Bed Airbnb - Brookline, MA
9.9 63 reviews

1 Free Parking Spot Coolidge Corner 1 Bed Airbnb

apartment, Brookline
This Brookline apartment is ideally located just 0.16 kilometers from Brookline Village’s T subway station, offering easy access to Fenway Park, Kenmore Square, and Back Bay.
The one-bedroom, one-bathroom flat sleeps three guests and includes amenities such as free Wi-Fi, parking, and toiletries; its proximity to Coolidge Corner provides numerous shops, restaurants, and the John F. Kennedy Presidential Library and Museum.
Family Friendly Neighborhood Spacious 3-bedrooms, 2 Baths,  Parking, Near Train. - Brookline, MA
8.0 1 review

Family Friendly Neighborhood Spacious 3-bedrooms, 2 Baths, Parking, Near Train.

apartment, Brookline
This three-bedroom flat is located in Brookline's Aspinwall Hill, 160 metres from Washington Square and a short walk to the C and D green lines for easy access to Boston's attractions.
This apartment sleeps six guests and offers two bathrooms, air conditioning, Wi-Fi, parking and a fully equipped kitchen, with Fenway Park and Boston Common within easy reach.
Victorian Condo - Brookline, MA
9.6 271 reviews

Victorian Condo

apartment, Boston
This four-bedroom flat is situated in a residential area a 15-minute drive from downtown Boston, with Fenway Park just 2 miles away. This property has received excellent ratings for its location, cleanliness, and overall experience, making it a great choice for travellers seeking a comfortable and convenient stay.
The 130 square metre apartment comfortably accommodates up to eight guests and features a spacious living room, a fully equipped kitchen, two bathrooms, and a private terrace. Guests can enjoy amenities such as laundry facilities, air conditioning, a jacuzzi, and a garden, as well as easy access to local restaurants and major attractions.
Remodeled Spacious Apartment In Perfect Location - Brookline, MA
10 31 reviews

Remodeled Spacious Apartment In Perfect Location

apartment, Boston
This apartment is located in Allston, a lively neighbourhood just a mile from Paradise Rock Club and within two miles of both Harvard University and Boston University. It has received excellent ratings from previous guests.
This three-bedroom flat can accommodate up to six guests and features a fully equipped kitchen, a modern living area, and a spa. Amenities include free WiFi, air conditioning, parking, and access to a range of nearby activities and attractions.

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

Beacon Hill: The Aldrich House - Brookline, MA
No reviews

Beacon Hill: The Aldrich House

apartment, Boston
This spacious four-bedroom flat is situated in Boston's historic Beacon Hill, offering excellent access to Boston Common (200 metres), Boston Public Garden (600 metres), and The Freedom Trail (500 metres).
This property boasts 557 square metres of floor area, accommodates eight guests, and includes amenities such as Wi-Fi, air conditioning, a private terrace, and on-site parking.
Perrin Place Unit 3 - Brookline, MA
8.6 35 reviews

Perrin Place Unit 3

apartment, Boston
Perrin Place Unit 3, a three-bedroom Boston flat, is conveniently located near Back Bay, approximately 3.8 km from the Hynes Convention Centre, 3.2 km from the Museum of Fine Arts, and under 5 km from both the John F. Kennedy Presidential Library and Museum and Fenway Park.
This 11-square-metre apartment sleeps 11 guests, boasting two bathrooms, a fully equipped kitchen with dishwasher, free Wi-Fi, and a private balcony; nearby opportunities for skiing and cycling are available.
Newly Renovated 4br Boston Apt W/ Kid Friendly - Exclusive Fifa 2026 Deal 90/2 - Brookline, MA
10 1 review

Newly Renovated 4br Boston Apt W/ Kid Friendly - Exclusive Fifa 2026 Deal 90/2

apartment, Boston
This Dorchester apartment is situated a 6-minute drive from the JFK Presidential Library and Museum and a 5-minute drive from Franklin Park Zoo, with Fields Corner underground station a 12-minute walk away for city exploration.
This spacious 4-bedroom, 2-bathroom flat accommodates up to 15 guests and offers amenities including air conditioning, free Wi-Fi, a fully equipped kitchen, and on-site parking, with laundry facilities and linens provided for your convenience.
Contemporary Farmhouse-style Retreat | Near T - Brookline, MA
9.6 19 reviews

Contemporary Farmhouse-style Retreat | Near T

apartment, Boston
This five-bedroom Roxbury flat is situated 0.8km from Franklin Park Zoo and 3.9km from Northeastern University, offering easy access to public transport.
The smoke-free property sleeps nine guests and boasts two bathrooms, a fully equipped kitchen including a dishwasher, in-unit laundry, and a private balcony; nearby attractions include the Longwood Medical Area and MCPHS University.

Best Brookline, MA holiday rentals with air conditioning

Comfy Oasis - Brookline, MA
9.9 71 reviews

Comfy Oasis

apartment, Boston
This apartment is situated in a quiet residential area of Boston, just a short distance from popular attractions like Franklin Park Zoo and Wollaston Beach. The apartment has been rated excellent for cleanliness and location, and very good overall.
The self-catering property has four bedrooms and two bathrooms, comfortably sleeping up to ten guests. It comes equipped with a full kitchen, air conditioning, a garden, and parking, making it a great choice for families or groups of friends visiting the city.
5br|3b  Families & Group  Hospitals  Downtown - Brookline, MA
9.6 23 reviews

5br|3b Families & Group Hospitals Downtown

apartment, Boston
This South Boston flat offers convenient access to transport links, being a 1.2-kilometre walk to Andrew Station and a 0.8-kilometre walk to South Bay Centre for amenities, with waterfront parks and beaches a 5-kilometre drive away.
This family-friendly five-bedroom flat sleeps up to eleven guests and features a fully equipped kitchen, in-unit laundry, central air conditioning, fast Wi-Fi, and smart lock self-check-in for a comfortable stay.
5es Remodeled Expansive Home, Off Street Parking - Brookline, MA
8.5 138 reviews

5es Remodeled Expansive Home, Off Street Parking

apartment, Milton
This five-bedroom house rental in Milton, Massachusetts, is situated within 16km of downtown Boston, offering easy access to public transport and local amenities.
Sleeping ten guests, this first-floor property boasts two bathrooms, a fully equipped kitchen including a fridge, microwave, and dishwasher, plus off-street parking; nearby shops and restaurants provide further convenience.
Renovated 1bed, Steps To Mbta, Shops & Restaurants - Brookline, MA
9.7 21 reviews

Renovated 1bed, Steps To Mbta, Shops & Restaurants

apartment, Brookline
This one-bedroom flat is located just a short distance from Coolidge Corner in Brookline, offering easy access to shops, restaurants, and public transport. The property has received excellent ratings for location, cleanliness, and overall user experience.
The flat is fully furnished and renovated, comfortably accommodating up to three guests. Amenities include a spacious living room with a workspace, a private outdoor space, a queen-sized bed, an en suite bathroom, and a fully equipped kitchen.
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