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Best Vacation rentals and Airbnb offers in Dorchester, MA
9.6 36 reviews
Dorchester, MA
08/07 – 08/09
$777/nighttotal: $1554 (2 )
Modern Home-like 3br2ba Retreat/near T
1 8
apartment , Boston
This three-bedroom, two-bathroom apartment in Dorchester, Boston, is conveniently located a two-minute walk from Savin Hill Train Station and one mile from Malibu Beach. The 3-bedroom rental boasts a designated office space, in-unit laundry, a fully equipped kitchen, high-speed internet, and sleeps up to nine guests, making it ideal for families or groups visiting Boston.
Dorchester, MA
06/27 – 07/04
$212/nighttotal: $1484 (7 )
Wonderful South End Studio
1 2
studio , Boston
This South End Boston apartment is a 13-minute walk from the Museum of Fine Arts and 1.2 miles from Fenway Park, offering easy access to Back Bay and other attractions. This pet-friendly unit boasts 970 square feet of space, sleeps two guests, and includes a kitchenette, free Wi-Fi, and air conditioning (seasonal).
Dorchester, MA
06/27 – 07/04
$325/nighttotal: $2275 (7 )
Bright & Cozy Studio Apartment
1 2
studio , Boston
This studio apartment is located on the border of Boston's South End and Back Bay neighborhoods, a historic 1900s brownstone offering quiet residential living with immediate access to dining and shopping. This approximately 360 sqft private unit accommodates two guests and includes a full bathroom, kitchen with a dishwasher, air conditioning, and internet, with 24/7 guest support available.
9.8 43 reviews
Dorchester, MA
08/07 – 08/09
$813/nighttotal: $1626 (2 )
New! Lux 3br W/ 400 Mbps Wifi | Roku Tv & Games!
1 8
apartment , Boston
This 3-bedroom townhouse in Boston's historic Fort Hill neighborhood offers proximity to Fenway Park, museums, and downtown attractions within a 10-minute radius, with Roxbury Crossing station an 8-minute walk away for a 20-minute Orange Line ride to Downtown Boston. This family-friendly rental features a stylish open-concept interior with towering ceilings, a fully equipped kitchen with stainless steel appliances and an island bar, HDTVs with streaming services, and is a 2-minute walk to a Bluebikes docking station, accommodating up to 10 guests with parking and internet included.
9.8 5 reviews
Dorchester, MA
08/07 – 08/09
$821/nighttotal: $1642 (2 )
Sleek 3br Boston - World Cup 2026 Escape - Near Franklin Park 60-3
3 8
apartment , Boston
This three-bedroom Boston apartment near Wollaston Beach offers a peaceful retreat, conveniently located 6.5 miles from Fenway Park and 7 miles from South Station. The 1300-square-foot rental boasts two bathrooms, free parking and Wi-Fi, a fully equipped kitchen, and accommodates up to 29 guests, perfect for large groups visiting Boston.
9.9 15 reviews
Dorchester, MA
06/27 – 07/04
$358/nighttotal: $2506 (7 )
Spacious Family Friendly Single-family Home In Jp
3 2
apartment , Boston
This Jamaica Plain, Boston rental home is conveniently located near the subway, providing easy access to Boston's attractions. The three-bedroom, two-bathroom house sleeps eight guests and features a fully equipped kitchen, fenced yards with a trampoline, and on-site hosts (except during guest stays) for assistance.
9.9 239 reviews
Dorchester, MA
06/27 – 07/04
$249/nighttotal: $1743 (7 )
Modern & Cozy 3-br Condo Near Downtown
3 2
apartment , Boston
This South Boston in-law suite offers a convenient location less than 3 miles from downtown Boston, near Carson Beach, Castle Island, and the John F. Kennedy Presidential Library and Museum. The three-bedroom, two-bathroom apartment sleeps four guests and features a fully equipped kitchen, in-unit laundry, free street parking, and 42" smart TVs in each bedroom.
8.3 3 reviews
Dorchester, MA
06/27 – 07/04
$275/nighttotal: $1925 (7 )
Wonderful 1br In Mission Hill
1 2
apartment , Boston
This 1-bedroom condo in Boston's Mission Hill is located 1.6 miles from Fenway Park and a 14-minute walk from the Museum of Fine Arts. This 540 sq ft rental accommodates up to 3 guests and includes a fully equipped kitchen with a dishwasher and oven, in-unit laundry, air conditioning, and free WiFi.
9.5 38 reviews
Dorchester, MA
06/27 – 07/04
$198/nighttotal: $1386 (7 )
Live By Fenway Park & Berklee College, #405
1 2
apartment , Boston
This Fenway District studio apartment offers easy access to Fenway Park and Boston's museums and restaurants. The unit features a queen-sized bed, a private bathroom with a glass shower, and coin-operated laundry in the building; it comfortably sleeps two guests and includes complimentary toiletries.
9.5 15 reviews
Dorchester, MA
08/07 – 08/09
$783/nighttotal: $1566 (2 )
82 - 3br Boston - Stylish Stay Near Mbta
3 8
apartment , Boston
This three-bedroom Boston apartment, located approximately 3.4 miles from the John F. Kennedy Presidential Library and Museum and 5 miles from both the Museum of Fine Arts and South Station, offers convenient access to major attractions. This 1300-square-foot rental boasts a fully equipped kitchen, private parking (a rarity in Boston!), a terrace, and can comfortably accommodate up to 25 guests.
9.0 4779 reviews
Dorchester, MA
06/27 – 07/04
$225/nighttotal: $1575 (7 )
Stylish Downtown Studio In The Southend, C.ave# 3
1 2
studio , Boston
This studio apartment is located in downtown Boston, just a short walk from Back Bay and the Hynes Convention Center, offering easy access to the city's attractions and vibrant atmosphere. The studio has received excellent ratings for cleanliness, location, and user experience, ensuring a comfortable and enjoyable stay. The studio features a comfortable sleeping area and a kitchenette with a microwave and toaster, perfect for light meal preparation. Guests can enjoy free Wi-Fi, air conditioning, and a convenient walk-in shower, making their stay comfortable and enjoyable.
8.5 4 reviews
Dorchester, MA
06/27 – 07/04
$227/nighttotal: $1589 (7 )
Stylish Studio In Historic Boston - Unit #209
1 2
studio , Boston
This Boston studio apartment is conveniently located near the Museum of Fine Arts, a short walk from Fenway Park, and within a couple of miles of Back Bay, MIT, and Boston University. The 150-square-foot unit sleeps two guests and features a kitchenette with a fridge and microwave, in-unit laundry, free Wi-Fi, cable TV, and air conditioning.
Discover Family-Friendly Vacation Rentals in Dorchester, MA
Booking a family-oriented vacation rental in Dorchester, MA keeps you close to top city attractions for a stress-free getaway.
Dorchester, MA
06/27 – 07/04
$487/nighttotal: $3409 (7 )
The Milton Manor 3br 1ba - Sleeps 6 - Unit 1 - Fifa World Cup 2026
3 2
apartment , Milton
This newly renovated apartment in Milton, located just south of Boston, offers easy access to major highways including Rt.138, Blue Hills Parkway, I-95, and I-93, with downtown Boston approximately a 20-minute drive away. This 1100-square-foot rental accommodates up to 6 guests in 3 bedrooms and features a modern kitchen with a fridge and microwave, air conditioning, WiFi, off-street parking for up to 4 small cars, and an in-unit washer and dryer, with the Blue Hills Reservation nearby for outdoor activities.
9.4 382 reviews
Dorchester, MA
06/27 – 07/04
$963/nighttotal: $6741 (7 )
World Cup Group Stay 5br Sleeps 16 Near Train Downtown\n
3 2
apartment , Boston
This house is located in Dorchester, a residential neighborhood in Boston, within a 3-mile radius of the University of Massachusetts Boston, Northeastern University, and the Boston Museum of Fine Arts. Guests have consistently rated the house excellent for cleanliness, location, and overall experience. The house has 5 bedrooms, making it suitable for larger families or groups. Amenities include free Wi-Fi, a fully equipped kitchen, a terrace, a garden, a spa, a restaurant, and parking.
10 1 review
Dorchester, MA
08/06 – 08/22
$579/nighttotal: $9264 (16 )
World Cup 2026 Getaway - Spacious 4br Near Boston - Free Parking 37-2
4 2
apartment , Boston
This 4-bedroom apartment is located approximately 6.2 miles from Logan Airport, offering convenient access for travelers visiting Boston. This spacious 1400 square foot residence includes complimentary private parking, high-speed WiFi, a fully equipped kitchen, and a 24-hour concierge, making it ideal for families and groups.
9.5 4 reviews
Dorchester, MA
08/06 – 08/22
$504/nighttotal: $8064 (16 )
80-3 3br Boston - Cozy Apt Near Dorchester Center
3 2
apartment , Boston
This three-bedroom Boston apartment is located near Harvard Square, approximately 3.4 miles from the John F. Kennedy Presidential Library and Museum and 5 miles from the Museum of Fine Arts. The 1190-square-foot rental boasts a spacious layout with a fully equipped kitchen, private balcony, on-site parking, and concierge service, accommodating up to 21 guests.
Best Dorchester, MA vacation rentals with parking
9.8 20 reviews
Dorchester, MA
08/07 – 08/09
$891/nighttotal: $1782 (2 )
Modern Home-like 3br2ba Retreat/minutes To T
3 8
apartment , Boston
This Boston apartment is located in Dorchester, just a short drive from the John F. Kennedy Presidential Library and Museum and Franklin Park Zoo. It's in a quiet, historic neighborhood with easy access to the city's attractions. This rental has received very good user ratings. The apartment has 3 bedrooms and 2 bathrooms, easily accommodating up to 9 guests. It comes with a fully equipped kitchen, in-unit laundry, air conditioning, a smart TV, and free Wi-Fi. You'll also enjoy a terrace/balcony, parking, and easy access to public transportation.
10 2 reviews
Dorchester, MA
06/27 – 07/04
$1266/nighttotal: $8862 (7 )
5br World Cup Stay Sleeps 16 Parking Walk To Train
5 2
apartment , Boston
This spacious Dorchester duplex, an 8-minute walk from a train station, is 5.7 miles from downtown Boston and the Boston Convention and Exhibition Center, and 3 miles from the beach. The five-bedroom, two-bathroom apartment sleeps 15 guests, features a microwave, dishwasher, in-unit laundry, free parking, and high-speed Wi-Fi, providing easy access to universities, restaurants, and breweries.
9.5 2 reviews
Dorchester, MA
08/07 – 08/09
$780/nighttotal: $1560 (2 )
Luxury 3br Apt In Boston That Sleeps 10
3 8
apartment , Boston
This 3-bedroom apartment in Boston is located approximately 2 miles from Fenway Park and 2.2 miles from Back Bay, offering convenient access to several key city attractions. This 1400 square foot residence features 3 bedrooms, 2 bathrooms, a fully equipped kitchen with a dishwasher, air conditioning, and parking, accommodating up to 19 guests with check-out at 10:00 AM.
10 2 reviews
Dorchester, MA
06/27 – 07/04
$574/nighttotal: $4018 (7 )
Charming Milton Escape- Blue Hills Views
3 2
apartment , Milton
This Milton vacation home, located near Franklin Park Zoo, Northeastern University, and Boston Medical Center, provides easy access to Boston via the Mattapan and Blue Hill Avenue MBTA stations. The 1790-square-foot house features three bedrooms, three bathrooms, and accommodates up to six guests, offering a fully equipped kitchen, laundry facilities, a fireplace, and convenient parking.
Frequently Asked Questions about vacation rentals in Dorchester, MA
What are the top family-friendly attractions in Dorchester, MA?
The Franklin Park Zoo is a must-visit for families. It's home to a wide variety of animals and has a great playground. The Dorchester Historical Society is also a great option for families, with exhibits on the history of Dorchester.
What are the best Airbnb and vacation rentals in Dorchester, MA?
When is the best time to book a vacation rental in Dorchester, MA?
Dorchester is a great place to visit year-round, but if you're looking for the best deals on vacation rentals, I'd recommend booking in the off-season, from November to March. You'll find lower prices and fewer crowds.
What are the most popular Airbnbs in Dorchester, MA?
What are the best budget-friendly activities in Dorchester, MA?
Take a walk or bike ride along the Neponset River. It's a beautiful, scenic route, and it's completely free. You can also check out the free events at the Codman Square Theatre.
What are the best vacation rentals with a pool in Dorchester, MA?
What are the best restaurants with local dishes in Dorchester, MA?
For authentic Caribbean food, you can't beat the Jerk Pit in Codman Square. If you're looking for something more casual, try the Dorchester Brewing Company. They have great craft beers and delicious pub fare.
What are the best rentals for families and kids in Dorchester, MA?
Are there pet-friendly attractions in Dorchester, MA?
The Franklin Park Zoo is pet-friendly, with designated areas where you can walk your dog. You can also find plenty of dog-friendly parks and walking trails throughout Dorchester.
What are the best rentals or Airbnbs with a jacuzzi in Dorchester, MA?
Top Vacation Rentals with Balconies in Dorchester, MA
Enjoy your own private terrace with city skyline views at these vacation rentals in Dorchester, MA.
Dorchester, MA
08/07 – 08/09
$875/nighttotal: $1750 (2 )
988 - 2 4br Boston Cozy Getaway Near Geneva Cliffs
4 8
apartment , Boston
This Boston apartment rental near Geneva Cliffs is conveniently located about 5 miles from both the Museum of Fine Arts and the Boston Convention and Exhibition Center, and also 5 miles from Logan International Airport. This spacious 1500-square-foot four-bedroom unit, ideal for large groups, offers two bathrooms, a fully equipped kitchen, private parking, a private terrace, and a 24-hour concierge.
10 7 reviews
Dorchester, MA
08/07 – 08/09
$1211/nighttotal: $2422 (2 )
Modern 5br 3ba Retreat Near Subway & Downtown Free Parking
5 8
apartment , Boston
This five-bedroom Dorchester duplex is a five-minute walk from Ashmont Station (Red Line), providing easy access to downtown Boston, Fenway Park, and the Seaport District. The spacious apartment features a modern open-concept layout, sleeps sixteen guests comfortably, includes a dedicated game room, and offers free on-site parking.
Dorchester, MA
08/07 – 08/09
$1062/nighttotal: $2124 (2 )
Chic 3br1.5ba City Stay - Near T + Parking
3 8
apartment , Boston
This 3-bedroom, 2-bathroom rental unit is located on the 3rd floor in Dorchester, Boston, a 7-10 minute walk (approximately 2,100-3,500 feet) from the Savin Hill T station, offering convenient access to Boston attractions. This family-friendly lodging accommodates up to 11 guests with futon sofas for flexible sleeping arrangements, and includes amenities such as a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace/balcony, garden, and 1 off-street parking space with free street parking.
9.0 17 reviews
Dorchester, MA
08/07 – 08/09
$659/nighttotal: $1318 (2 )
74r - 2br Quincy - Romantic Stay Near Wollaston Beach
2 8
apartment , Quincy
This Tirrel Street rental in Quincy, MA, offers a convenient location near Wollaston Beach and downtown Quincy, providing easy access to local attractions. This 1,100-square-foot apartment features two bedrooms, one bathroom, and sleeps up to nine guests (with extra fees after four), boasting a fully equipped kitchen, in-unit laundry, central A/C, and one reserved parking space.
Neighborhoods and points of interest in Dorchester, MA
Best Dorchester, MA vacation rentals with air conditioning
9.6 16 reviews
Dorchester, MA
08/07 – 08/09
$845/nighttotal: $1690 (2 )
Stylish 3br Boston Stay W/parking Near Red Line 82
1 8
apartment , Boston
This spacious 1300-square-foot Boston apartment is conveniently located near the MBTA, a mile from an Asian supermarket, and within a 20-minute drive of Fenway Park, Harvard Square, and Logan International Airport. The three-bedroom, two-bathroom unit sleeps up to 13 guests and features a fully equipped kitchen, in-unit laundry, free parking, and pet-friendly accommodations.
10 117 reviews
Dorchester, MA
08/06 – 08/22
$251/nighttotal: $4016 (16 )
Extraordinary 1-bedroom Apartment In South Boston!
1 2
apartment , Boston
This South Boston apartment rental is ideally located near Carson Beach and the L Street Bathhouse, a 1.5-mile trip from the Boston Convention and Exhibition Center. The one-bedroom, one-bathroom unit sleeps three guests comfortably, featuring a queen-size bed, a queen-size pull-out couch, a fully equipped kitchen with dishwasher, high-speed internet, and easy access to public transportation.
9.5 35 reviews
Dorchester, MA
08/06 – 08/22
$220/nighttotal: $3520 (16 )
Spacious 1br Home Close To Train & Downtown
1 2
apartment , Boston
This Jamaica Plain condo, a first-floor unit offering easy access to shops, restaurants, and the MBTA's Orange Line, provides a convenient base for exploring Boston. The one-bedroom, one-bathroom apartment sleeps three, features a private deck and backyard with fire pit, a fully equipped kitchen including a dishwasher, and shared laundry facilities; free street parking is also available.
Dorchester, MA
06/27 – 07/04
$302/nighttotal: $2114 (7 )
Peaceful Back Bay Studio
1 2
studio , Boston
This studio apartment is located in Boston's Back Bay, bordering the South End and Massachusetts Avenue, placing it 0.5 miles from Northeastern University and within easy reach of major Boston hospitals like Brigham and Women's Hospital and Boston Children's Hospital. This 290 sqft studio offers a full private bathroom, a kitchen with a fridge and oven, and accommodates up to 2 guests, with amenities including internet and air conditioning, and is situated near Southwest Corridor Park for outdoor recreation.
