Vacation Rentals in Brookline, MA

1019 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Brookline, MA holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

1019 Holiday rentals and Airbnb in Brookline, MA

Uncover Top-Tier Family Holiday Rentals in Brookline, MA, United States

Give the entire crew plenty of space to relax and unwind after a busy day of sightseeing at family holiday rentals in Brookline, MA, United States.

Modern Beautiful Apartment-5 Beds-full Kitchen-parking-super Clean-great For Groups - Brookline, MA
9.2 356 reviews

Modern Beautiful Apartment-5 Beds-full Kitchen-parking-super Clean-great For Groups

apartment, Boston
This apartment is situated in a peaceful neighbourhood, approximately 7 miles from the Boston Museum of Fine Arts, Fenway Park, and the Hynes Convention Center, offering a tranquil escape from the city centre while remaining conveniently close to major attractions. It consistently receives excellent ratings for cleanliness, location, and overall user experience.
This spacious flat can comfortably accommodate families or groups of friends with its five beds. Guests can enjoy a range of amenities, including a fully equipped kitchen, private parking, a balcony or terrace with garden views, and access to a garden, making it ideal for a relaxing and enjoyable stay in Boston.
Pretzel Factory Loft W/peloton - Brookline, MA
9.8 173 reviews

Pretzel Factory Loft W/peloton

apartment, Brookline
This four-bedroom flat is located in Brookline Village, a short walk from the T (subway) and the hospital district. It has received excellent ratings for location, cleanliness, and overall user experience.
The flat features a spacious open-plan living area, kitchen, and dining room, providing ample space for families or groups. Amenities include a private garage, a garden, a fitness centre, fast Wi-Fi, a Sonos sound system, and a Peloton+.
Hidden Gem 2 Br/1ba Near Zoo 3 Mil Downtown Fenway - Brookline, MA
10 29 reviews

Hidden Gem 2 Br/1ba Near Zoo 3 Mil Downtown Fenway

apartment, Boston
This Roxbury flat is situated 1.4 km from Boston Medical Centre, 4.8 km from Northeastern University, and 4.8 km from Copley Square, offering easy access to public transport via Newmarket and Uphams Corner stations.
This two-bedroom, one-bathroom apartment sleeps six, featuring a fully equipped kitchen, free Wi-Fi, a Smart TV, and is within easy reach of Fenway Park and Boston Common.
Harmony Medical Suites Chinatown - Brookline, MA
8.0 145 reviews

Harmony Medical Suites Chinatown

studio, Boston
This Boston flat is situated in Chinatown, offering convenient access to the city centre within 700 metres, a six-minute walk to Boston South Station and the Freedom Trail, and an eleven-minute walk to the Boston Tea Party Ship & Museum.
This apartment provides air-conditioned accommodation with complimentary WiFi, a kitchen equipped with a fridge, microwave, and dishwasher, and on-site fitness facilities, with parking also available.

Best Brookline, MA holiday rentals with parking

Spacious 4br/4ba  Great For Groups & Long Stays - Brookline, MA
10 96 reviews

Spacious 4br/4ba Great For Groups & Long Stays

apartment, Boston
This four-bedroom apartment is located just a short distance from Boston's main attractions, universities, and hospitals, making it a convenient base for exploring the city. It has consistently received excellent ratings for its cleanliness, location, and overall user experience.
The apartment is spacious and comfortably accommodates up to eight guests. It features four private bathrooms, two private outdoor porches, a fully equipped kitchen, and a range of amenities, including high-speed Wi-Fi, central heating and air conditioning, a washer and dryer, and free street parking.
Bright And Spacious 3br Apt, Gated 2 Car Parking - Brookline, MA
10 14 reviews

Bright And Spacious 3br Apt, Gated 2 Car Parking

apartment, Boston
This three-bedroom flat in Boston is situated in a well-connected neighbourhood, a 10-12 minute walk from the Stony Brook Orange Line train station, offering straightforward access to downtown Boston.
This spacious apartment accommodates up to six guests, featuring vaulted ceilings, exposed beams, a fully equipped eat-in kitchen with a dishwasher and island, in-unit laundry, central heating and air conditioning, and private driveway parking for three cars.
3 Bedroom Apartment Next To T Stop / Off Street Parking - Brookline, MA
9.7 79 reviews

3 Bedroom Apartment Next To T Stop / Off Street Parking

apartment, Boston
This charming bed and breakfast is located in a quiet residential area just 1.6 km from Sullivan Station on the Orange Line T, providing easy access to downtown Boston and Cambridge. The property consistently receives excellent ratings for cleanliness, location, and overall guest experience.
The apartment features a separate bedroom, an open-plan living and dining area, and a fully equipped kitchen. Guests enjoy free high-speed internet, basic cable, and laundry access (for stays longer than 5 days), as well as convenient keyless entry and parking options nearby.
Boston's Best Vacation Home - Brookline, MA
9.8 117 reviews

Boston's Best Vacation Home

apartment, Boston
This smoke-free house is located in Mattapan, a quiet residential neighbourhood in Boston, just 3.8 kilometres from Franklin Park Zoo and within 9.6 kilometres of Northeastern University and the Boston Museum of Fine Arts. The house has excellent user, location and cleanliness ratings, making it a great choice for travellers looking for a comfortable and convenient stay.
The house has 3 bedrooms and 2 bathrooms, covering 111 square metres and accommodating up to 6 guests. It includes a kitchen, a fireplace, a washing machine, a TV, and a hair dryer, as well as a garden and parking.

Frequently asked questions about holiday rentals in Brookline, MA

  • What are the top family-friendly attractions in Brookline, MA?

    Brookline has plenty to keep families entertained. The Brookline Recreation Department offers a variety of programmes and activities for kids, including the Brookline Teen Center. The Children's Museum in Boston is also just a short drive away and is a great place for a fun-filled day out.
  • What are the best Airbnb and holiday 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 or September to October. You'll avoid the summer crowds and enjoy pleasant weather, while still being able to participate in many outdoor activities.
  • What are the most popular Airbnbs in Brookline, MA?

  • What events or festivals should visitors check out in and around Brookline, MA?

    Brookline hosts several events throughout the year, including the Brookline Farmers Market, the Brookline Open Studios, and the Brookline Arts Center's annual art festival. Be sure to check out the event calendar on the town's website for more details.
  • What are the best holiday rentals with a pool in Brookline, MA?

  • What are the best budget-friendly activities in Brookline, MA?

    Brookline offers plenty of free or low-cost activities. You can enjoy a picnic in the beautiful grounds of the Arnold Arboretum, take a walk or cycle along the Charles River, or visit the free exhibits at the Brookline Public Library.
  • 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 local cuisine, try the classic New England fare at The Publick House, or for a more modern take, head to The Blue Room, which features a seasonal menu with local ingredients.
  • What are the best rentals or Airbnbs with a jacuzzi in Brookline, MA?

    The best holiday 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 is a great option for a scenic walk or cycle. It's a series of parks and green spaces that connect Brookline to Boston. For a shorter route, try the paved path along the Charles River.
  • Are there pet-friendly attractions in Brookline, MA?

    Many of Brookline's parks and green spaces are dog-friendly, including the Arnold Arboretum and the Charles River Esplanade. You can also find pet-friendly restaurants and cafes in the area.
  • What are the benefits of choosing a vacation rental in Brookline, MA?

    Vacation rentals offer more space and privacy than hotels, as well as the opportunity to cook your own meals. They're also often located in residential areas, giving you a more authentic experience of Brookline.

Popular destinations

Discover Holiday Rentals with a Balcony in Brookline, MA, United States

Relax outdoors and watch the town come alive from the elevated vantage of holiday rentals with a balcony in Brookline, MA, United States.

Upscale Unit 3 At Perrin Place - Brookline, MA
9.4 54 reviews

Upscale Unit 3 At Perrin Place

apartment, Boston
This Roxbury flat is situated within a 4.8km radius of Boston Medical Centre, Northeastern University, Copley Square, Fenway Park, and Boston Common.
This spacious 116 square metre, three-bedroom property sleeps six, boasting a fully equipped kitchen, private balcony, jacuzzi, and free Wi-Fi; nearby, Boston Uphams Corner and Newmarket stations offer easy public transport access.
4br Dorchester Home - Near Marina Bay & Parks - Sun-filled Summer Getaway 90-3 - Brookline, MA
8.7 44 reviews

4br Dorchester Home - Near Marina Bay & Parks - Sun-filled Summer Getaway 90-3

apartment, Boston
This four-bedroom flat is located in Boston, just five miles from the city centre and major attractions like the Boston Convention Exhibitors Centre and Hynes Convention Center, in a quiet residential neighbourhood. The apartment has received very good user ratings and a good location rating.
The flat offers 177 square metres of space, comfortably accommodating up to 14 guests. Amenities include free Wi-Fi, parking, a fully equipped kitchen, air conditioning, and a flat-screen TV.
Comfy & Chic Apartment For 2026 World Cup Free Parking - Brookline, MA
9.5 2 reviews

Comfy & Chic Apartment For 2026 World Cup Free Parking

apartment, Boston
This Boston apartment, situated approximately 10-11 kilometres from attractions such as the Museum of Fine Arts and Fenway Park, offers convenient access to major landmarks.
The 107-square-metre property features three bedrooms, one bathroom, sleeping up to eleven guests, and includes amenities such as a fully equipped kitchen, Wi-Fi, air conditioning, a terrace, and private parking.
Cozy As A Sunday - 2/br Sleep 6 - Brookline, MA
10 1 review

Cozy As A Sunday - 2/br Sleep 6

apartment, Everett
This two-bedroom apartment is situated in Everett, just 6.8 km from the Freedom Trail, 6.9 km from North Station, and 7 km from TD Garden, offering easy access to Boston's main attractions. It is a convenient base for exploring the city and surrounding areas.
This spacious flat has a floor area of 111 square metres and can accommodate up to 11 guests. The apartment offers a comfortable living space with a balcony, a well-equipped kitchen, and modern amenities such as a flat-screen TV and free Wi-Fi.

Best Brookline, MA holiday rentals with air conditioning

Comfy & Chic 3 Bedroom In Boston W/ Free Parking - Brookline, MA
9.7 52 reviews

Comfy & Chic 3 Bedroom In Boston W/ Free Parking

apartment, Boston
This three-bedroom Boston apartment, situated in a peaceful neighbourhood with convenient access to downtown Boston and the upscale shopping and dining of Chestnut Hill and Legacy Place (distances unspecified), offers a comfortable base for exploring the city and its surroundings.
The 3-bedroom, 1-bathroom flat sleeps six guests, features in-unit laundry, a fully equipped kitchen including a dishwasher, air conditioning, a garden, parking, and complimentary espresso and organic lemonade upon arrival.
2min->coolidge&greent/king Bed/full Kitchen/arcade - Brookline, MA
No reviews

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

apartment, Brookline
This Brookline apartment, located in Coolidge Corner's South Side, offers a three-minute walk to the Green Line T station, providing easy access to Boston city centre and Longwood Medical Area.
The two-bedroom flat sleeps five, features a 65-inch 4K Smart TV, a fully equipped kitchen, and a Galaga arcade game, with daily parking available for £18 at a nearby private lot.
Cozy Apartment - Bu/fenway/longwood- Free Parking! - Brookline, MA
9.6 342 reviews

Cozy Apartment - Bu/fenway/longwood- Free Parking!

apartment, Brookline
This one-bedroom apartment in Brookline is located just 2 km from Downtown Boston and less than 1.5 km from attractions like Kenmore Square, Newbury Street, and Back Bay, offering a convenient base for exploring the city. The apartment has consistently received excellent ratings for location, cleanliness, and overall user experience.
The flat offers a spacious living room with a comfortable sofa bed, a fully equipped kitchen, and a bedroom with two queen-size beds, comfortably accommodating up to 6 guests. Guests can enjoy modern amenities such as air conditioning, a dishwasher, and a dedicated workspace, along with convenient extras like parking, laundry facilities, and a range of essential supplies.
The Hunter: Comfortable  Bright  Amenities! - Brookline, MA
9.6 60 reviews

The Hunter: Comfortable Bright Amenities!

apartment, Boston
This two-bedroom Boston apartment, ideally located near Boston College and Harvard University, is a short 0.8 km walk from the T subway, providing easy access to the city.
The 2-bathroom flat offers two queen beds, sleeping up to five guests, and boasts amenities including a fully equipped kitchen, in-unit laundry, and access to a complex with a swimming pool, fitness centre, and games room; plus, blazing-fast Wi-Fi.

Book Your Next Luxury Holiday Rental in Brookline, MA, United States

Indulge in an upscale urban escape featuring elegant living spaces and concierge quality at luxury holiday rentals in Brookline, MA, United States.

New! Lux 3br W/ 400 Mbps Wifi | Roku Tv & Games! - Brookline, MA
9.5 56 reviews

New! Lux 3br W/ 400 Mbps Wifi | Roku Tv & Games!

apartment, Boston

Browse Downtown Holiday Rentals in Brookline, MA, United States

Spend less time on public transport and more time visiting nearby sights from centrally located holiday rentals in Brookline, MA, United States.

Min>coolidge | 65in Tv - 2 - Brookline, MA
9.9 37 reviews

Min>coolidge | 65in Tv - 2

apartment, Brookline
Min>coolidge | King Bed|full Kitchen|laundry - Brookline, MA
9.8 55 reviews

Min>coolidge | King Bed|full Kitchen|laundry

apartment, Brookline
Pretzel Factory Loft W/peloton - Brookline, MA
9.8 173 reviews

Pretzel Factory Loft W/peloton

apartment, Brookline
Skyrise Two Stories - Centrally Located - Brookline, MA
9.5 204 reviews

Skyrise Two Stories - Centrally Located

apartment, Brookline
©2026 cozycozy.com