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

Sunny Dog Friendly Union Sq 1brm - Brookline, MA
9.4 140 reviews

Sunny Dog Friendly Union Sq 1brm

apartment, Somerville
This Somerville flat is perfectly situated, just a short walk from both the Gilman Square and Union Square T stops, making it easy to explore the city. It has received excellent ratings for location, cleanliness, and overall experience, ensuring a comfortable stay.
The flat has one bedroom and one bathroom, comfortably accommodating up to four guests. It offers a well-equipped kitchen, free parking, and a private outdoor space, perfect for relaxing after a day of exploring the local shops and restaurants.
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.
The Milton Manor 3br 1ba - Sleeps 6 - Unit 1 - Brookline, MA
No reviews

The Milton Manor 3br 1ba - Sleeps 6 - Unit 1

apartment, Milton
This newly renovated flat in Milton, located south of Boston, offers convenient access to Route 138, Blue Hills Parkway, I-95, and I-93, placing you just a 32-kilometre drive from downtown Boston and a short distance from the Blue Hills Reservation for outdoor recreation.
This family-friendly property spans 102 square metres, featuring three bedrooms to accommodate up to six guests, with amenities including high-speed Wi-Fi, a fully equipped kitchen, an in-unit washer/dryer, and off-street parking for up to four small cars.
The Holmes : Chic  Sun-soaked  W/d! - Brookline, MA
9.4 107 reviews

The Holmes : Chic Sun-soaked W/d!

apartment, Boston
This apartment is situated just 5km from Boston College and Harvard, close to the T (public transport) and Whole Foods, making it an ideal base for exploring the city. The apartment has consistently received excellent ratings for user experience, location, and cleanliness.
The flat is a modern, one-bedroom property that can comfortably accommodate up to 5 guests. This spacious accommodation offers a fully equipped kitchen, a washer and dryer, a 65" Roku TV, and free Wi-Fi, along with access to a shared gym, pool, and lounge areas.

Best Brookline, MA holiday rentals with parking

The Apgar: Cozy  Inviting  Amenities! - Brookline, MA
9.6 103 reviews

The Apgar: Cozy Inviting Amenities!

apartment, Boston
This luxe junior one-bedroom apartment is situated near Boston College and Harvard University, a short 0.8 km walk from the MBTA subway (T).
The self-contained studio, sleeping up to four guests, boasts a fully equipped kitchen, in-unit laundry, a 65" SmartTV, high-speed Wi-Fi, and access to building amenities including a swimming pool, fitness centre, and games rooms; monthly parking is available for £240.
The Fleming: Groups  Spacious  Private Patio - Brookline, MA
9.8 60 reviews

The Fleming: Groups Spacious Private Patio

apartment, Boston
This Boston studio flat, near Boston College and Harvard University, enjoys a convenient location less than 0.8km from the T subway providing easy access to the city.
The self-contained apartment sleeps three, features a fully equipped kitchen, in-unit laundry, a 65” Roku TV, blazing-fast WiFi and access to a building complex with multiple lounges, kitchens, meeting spaces, a gym, and games areas.
Stylish 1br In Malden #3 - Brookline, MA
9.0 157 reviews

Stylish 1br In Malden #3

apartment, Malden
This Malden flat is located just 4.7 km from Cambridge College, 6.1 km from Inman Square, and 6.7 km from the Peabody Museum, offering easy access to local attractions and a peaceful setting away from the hustle and bustle of Boston. The flat has received excellent ratings for cleanliness, location, and overall experience, making it a great choice for travellers seeking a comfortable and convenient stay.
The flat has one bedroom and one bathroom, providing a comfortable space for a single traveller or a couple. Amenities include air conditioning, a fully equipped kitchen with a fridge, microwave, and dishwasher, and free parking, ensuring a comfortable and convenient stay.
1 Free Parking Spot, Coolidge Corner 1 Bed - Brookline, MA
No reviews

1 Free Parking Spot, Coolidge Corner 1 Bed

apartment, Brookline
This one-bedroom flat in North Brookline is located just 160 metres from the T, providing straightforward access to Fenway Park, Kenmore Square, and Back Bay.
The pet-friendly accommodation offers private living for two guests, featuring a fully equipped kitchen, complimentary parking, and is situated within walking distance of numerous shops and restaurants.

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 Red Door Haven +5mins To Boston - Brookline, MA
No reviews

Modern Red Door Haven +5mins To Boston

apartment, Milton
Book this vacation rental. This accommodation is located in Milton.
Facilities and services: a washing machine, a dish washer and a terrace. This apartment in Milton also has air conditioning!
Rare Boston 12br | Yard, Fire Pit + Grills - Brookline, MA
9.4 374 reviews

Rare Boston 12br | Yard, Fire Pit + Grills

apartment, Boston
This charming house is conveniently located in Dorchester, just a short distance from the University of Massachusetts Boston, Northeastern University, and the Boston Museum of Fine Arts. The property has received excellent ratings for cleanliness and location, making it a popular choice for travellers.
The accommodation offers five bedrooms, making it ideal for larger groups or families. Guests can enjoy a range of amenities, including a fully equipped kitchen, a terrace, a garden, a spa, a restaurant, and parking, as well as access to barbecue grills and free WiFi.
3br2bth Td Garden/mit/harvard/bos/3 Parking Spaces - Brookline, MA
10 28 reviews

3br2bth Td Garden/mit/harvard/bos/3 Parking Spaces

apartment, Somerville
This East Somerville flat is situated near the Sullivan Square tube station (a 0.4km walk), Assembly Row (0.6km walk), offering easy access to Kendall Square, MIT, and Boston city centre.
The four-bedroom property, sleeping up to eight guests, includes a fully equipped kitchen, in-unit laundry, free parking for two cars, and family-friendly amenities such as a high chair and cot (available on request).
Spacious 5 Br Boston Home Near Train & Parking - Brookline, MA
No reviews

Spacious 5 Br Boston Home Near Train & Parking

apartment, Boston
This 5-bedroom Boston flat is located between 5.5 and 7.4 kilometres from the JFK Presidential Library & Museum and the Boston Tea Party Ship & Museum, with Logan Airport situated 8 kilometres away.
This spacious flat offers 5 bedrooms, can accommodate up to 29 guests, and features private parking, complimentary WiFi, a garden, a terrace, and a fully equipped kitchen, with air conditioning for comfort.

Best Brookline, MA holiday rentals with air conditioning

The Warren : Groups  Elegant  Cozy  W/d  Pool - Brookline, MA
9.8 114 reviews

The Warren : Groups Elegant Cozy W/d Pool

apartment, Boston
This studio apartment is located just 5 kilometres from Boston College and Harvard University, a short walk from the T (public transport) and close to a range of amenities. It has received excellent ratings for cleanliness, location and user experience.
The self-catering unit has a separate bedroom with a sliding door and can accommodate up to four guests. The apartment has a fully equipped kitchen, a washer and dryer, fast Wi-Fi, a smart TV, and access to a shared complex with lounges, kitchens, meeting spaces, a gym and a swimming pool.
(476-6) 2beds, Cozy Home, Prime Location! - Brookline, MA
9.7 40 reviews

(476-6) 2beds, Cozy Home, Prime Location!

apartment, Boston
This Boston flat is conveniently located on Columbus Avenue in the Back Bay/South End, offering easy access to various restaurants and shops, and is a short distance from many Boston attractions.
The self-catering apartment, sleeping one guest, features a fully equipped kitchen (with toaster oven), a shared roof deck with city views, shared laundry facilities, and air conditioning (window units available upon request); a 10% discount is available for medical/hospital stays, with a charitable donation as an alternative.
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.
(Pg03) Cozy Budget-friendly Studio In Fenway - Brookline, MA
9.4 126 reviews

(Pg03) Cozy Budget-friendly Studio In Fenway

apartment, Boston
This garden-level apartment is located in Boston's Fenway-Kenmore area, close to Fenway Park and easily accessible by public transport.
The self-contained unit sleeps two, features a well-equipped kitchen with fridge, freezer and microwave, a queen-size bed, TV, and keyless entry; a pack 'n play is available, and a 10% discount applies for medical stays, with charitable donations otherwise.
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