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

Spacious Medford Gem - Brookline, MA
9.9 30 reviews

Spacious Medford Gem

apartment, Medford
This two-bedroom apartment in Medford is conveniently situated just 5 kilometres from Harvard Square, placing you within easy reach of the city's cultural attractions.
The 167 square metre property offers ample space for up to 15 guests, with a fully-equipped kitchen, free Wi-Fi, air conditioning, and private parking.
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.
2br Spacious & Comfy 43' Yacht - Heat & Ac - On The Freedom Trail - Best Nights Sleep - Brookline, MA
9.8 273 reviews

2br Spacious & Comfy 43' Yacht - Heat & Ac - On The Freedom Trail - Best Nights Sleep

boat, Boston
This boat is located in Boston, just a short distance from the Freedom Trail, Boston North Station, and TD Garden, offering easy access to the city's main attractions. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The 46-square-metre vessel comfortably sleeps up to five guests in its two bedrooms and two bathrooms. Enjoy a fully equipped kitchen, a private terrace with sea views, free Wi-Fi, and the convenience of private parking.
Spacious Sunny Charming Apartment, Patio, Parking - Brookline, MA
9.8 23 reviews

Spacious Sunny Charming Apartment, Patio, Parking

apartment, Boston
This two-bedroom flat in Boston offers a convenient urban experience, located a short distance from the city's attractions in a quiet residential area with easy access to public transport, shops, and dining.
This pet-friendly, family-suitable apartment accommodates up to six guests and features a private patio with seating and a grill, a fully equipped kitchen with a fridge, microwave, and dishwasher, and air conditioning for comfort.

Best Brookline, MA holiday rentals with parking

Charming 2-story Private Guesthouse - Brookline, MA
9.9 254 reviews

Charming 2-story Private Guesthouse

house, Newton
This charming guesthouse is located in Newton, just a short distance from Boston and close to I-90, making it a convenient base for exploring the area. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property offers a comfortable living space with a living room, solarium, bedroom, and a private deck. It can accommodate up to four guests and features modern amenities, including a well-equipped kitchen, a large backyard with a swimming pool, and access to a range of streaming services on a smart TV.
2 Free Parking Spots- In Unit Washer/dryer - Brookline, MA
No reviews

2 Free Parking Spots- In Unit Washer/dryer

apartment, Brookline
This Washington Square flat offers a prime Brookline location, situated just 160 meters from the T subway station, providing swift access to Fenway Park, Kenmore Square, and Back Bay.
This private one-bedroom flat accommodates up to four guests with a queen bed and sofa bed, featuring a fully equipped kitchen, modern amenities including a flat-screen TV, and included parking, with Boston University, Boston College, and the Longwood Medical Area within easy reach.
The Dalton - The Upton Boston, South End - Brookline, MA
9.7 329 reviews

The Dalton - The Upton Boston, South End

apartment, Boston
This charming apartment is situated in the South End, just a short walk from Copley Square, The Prudential, Newbury Street, and Boston Commons, providing easy access to the city's most popular attractions. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has one bedroom and one bathroom, and is equipped with a fully equipped kitchen, a washer and dryer, and modern amenities such as a queen-size bed, a 48" flat-screen TV, and high-speed internet. Guests can enjoy the convenience of a private apartment with a quiet setting, ideal for a comfortable stay in Boston.
Modern 1br Near Encore Zb9m - Brookline, MA
9.0 2 reviews

Modern 1br Near Encore Zb9m

apartment, Everett
This Everett apartment, situated near the Encore Boston Harbor casino (a 1.6km walk), offers easy access to Boston attractions such as the Seaport and Fenway Park (a 17-24km drive).
The 65 square metre flat comprises one bedroom, one bathroom, and accommodates three guests, boasting amenities including a fully equipped kitchen, free on-site parking, and a self-check-in system.

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

Modern/luxury | Steps From Zoo & Golf Course - Brookline, MA
9.8 57 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.
Luxury Apartments By Hyatus Boston Somerville - Brookline, MA
No reviews

Luxury Apartments By Hyatus Boston Somerville

apartment, Somerville
This Somerville flat is a short walk from the city centre, with Sullivan Square, Assembly Row Shopping Centre, and Round Corner House within easy reach.
This pet-friendly apartment offers guests a microwave oven, dishwasher, air conditioning, and access to an outdoor swimming pool, barbecue area, and on-site fitness centre, with a maximum capacity of two people.
5 Br Boston Townhouse Near Downtown Parking, Backyard & Walk To Train - Brookline, MA
10 2 reviews

5 Br Boston Townhouse Near Downtown Parking, Backyard & Walk To Train

apartment, Boston
This Dorchester, Boston flat is conveniently located near the 'T' subway, offering easy access to attractions such as Boston Common and the Boston Harbour.
The spacious five-bedroom duplex sleeps fifteen guests, boasting a fully equipped kitchen with dishwasher, in-unit laundry, driveway parking, and free Wi-Fi.
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

Simple 2 Bed 2 Bath Close To Fenway - Brookline, MA
8.8 9 reviews

Simple 2 Bed 2 Bath Close To Fenway

apartment, Boston
This Fenway-adjacent flat is conveniently located a short walk from Fenway Park and within 3.2 kilometres of Back Bay, MIT, and Boston city centre.
The 90-square-metre property boasts two bedrooms, two bathrooms, sleeps seven guests, and includes a fully equipped kitchen with microwave, free Wi-Fi, air conditioning (seasonal), and pet-friendly options (dogs allowed with a cleaning fee).
(New1f) Front-facing 1br On Newbury Street - Brookline, MA
8.5 12 reviews

(New1f) Front-facing 1br On Newbury Street

apartment, Boston
This one-bedroom flat is located in Boston's Back Bay, a short walk from Newbury Street, the Prudential Centre, and Copley Square, and is conveniently close to major hospitals and universities.
This apartment offers accommodation for two guests with air conditioning, a kitchen equipped with a fridge, freezer, and microwave, and a private bathroom, with a pack-and-play crib available upon request.
Stylish, Comfortable Luxury | Near T - Brookline, MA
9.6 58 reviews

Stylish, Comfortable Luxury | Near T

apartment, Boston
This three-bedroom, two-bathroom apartment in Boston's Savin Hill neighbourhood is conveniently located near Savin Hill T station on the Red Line, offering easy access to central Boston.
The open-plan flat sleeps eight guests, boasting a fully equipped kitchen with dishwasher, high-speed internet, air conditioning, and high-quality memory foam mattresses; on-street parking is available (charges may apply).
Stylish Studio In Historic Boston #208 - Brookline, MA
9.0 3 reviews

Stylish Studio In Historic Boston #208

studio, Boston
This Boston studio apartment is centrally located, 0.6km from the Hynes Convention Centre and 0.8km from Fenway Park, offering easy access to Boston University, the Boston Public Garden, and other attractions.
The 14 square metre self-catering unit sleeps two guests and includes a kitchenette with fridge and microwave, air conditioning, free Wi-Fi, and city views.
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