Vacation Rentals in Boston, MA

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Boston, MA vacation rentals
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10420 Vacation rentals and Airbnb in Boston, MA

Best family friendly Boston, MA vacation rentals

Among the 10420 accommodations in Boston, MA, here are the 4 best family friendly rentals

Family/business | Yard + Bbq + Parking | Game Room - Boston, MA
9.1 9 reviews

Family/business | Yard + Bbq + Parking | Game Room

apartment, Somerville
This 7-bedroom, 5-bathroom luxurious apartment in Somerville offers prime positioning, being a mere 500 to 1000 metres on foot from Tufts University and the local subway station.
This exceptionally rated residence provides ample space for up to 16 guests, featuring a modern kitchen with integrated appliances, air conditioning, on-site laundry facilities, and outdoor seating, making it ideal for families visiting Somerville.
Charming South-end Condo With Large Outdoor Patio - Boston, MA
9.8 399 reviews

Charming South-end Condo With Large Outdoor Patio

apartment, Boston
This one-bedroom flat is located in Boston’s historic South End, within a short walk of major tourist attractions, sporting venues, and medical facilities. This property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The flat comfortably sleeps four guests with a queen-size bed in the bedroom and a sofa bed in the living room. It is fully equipped with a kitchen, washer and dryer, a spacious outdoor deck, and a range of amenities including toiletries, a hairdryer, and a first aid kit.
Single Family Boston House Great Privacy - Boston, MA
9.8 56 reviews

Single Family Boston House Great Privacy

apartment, Boston
This spacious Metro Boston Airbnb, located in a suburban area offering easy access to the city's attractions, provides a convenient base for exploring the historical sites and cultural gems of the city.
This five-bedroom, three-bathroom house boasts 246 square metres of living space, three decks, a large private garden, parking, and sleeps up to ten guests, making it ideal for families or groups visiting Boston.
Inviting 4br Boston Apt - Kid Friendly - Near I-95 & Free Parking 90-2 - Boston, MA
10 1 review

Inviting 4br Boston Apt - Kid Friendly - Near I-95 & Free Parking 90-2

apartment, Boston
This modern four-bedroom flat in Boston is located 4.2 kilometres from the John F. Kennedy Presidential Library and Museum and 6.9 kilometres from the Museum of Fine Arts, offering convenient access to notable attractions.
This family-friendly residence boasts 121 square metres of living space, accommodating up to 29 guests with two bathrooms, a fully equipped kitchen featuring a dishwasher and microwave, air conditioning, a balcony, and complimentary Wi-Fi and private parking.

Best Boston, MA vacation rentals with a pool

Among the 10420 accommodations in Boston, MA, here are the 4 best rentals with a pool

Walk To Mit & T Stop! Kendall Square Extended Base - Boston, MA
No reviews

Walk To Mit & T Stop! Kendall Square Extended Base

apartment, Cambridge
This Cambridge flat is located in East Cambridge, a short walk from Kendall Square and the Massachusetts Institute of Technology (MIT), with public transport links including Kendall-MIT Station 550 metres away and Lechmere Station 1.1 kilometres away, and TD Garden a 3-minute drive.
This 102 square metre residence offers two bedrooms, two bathrooms and accommodation for four guests, featuring a fully equipped kitchen, air conditioning, internet, on-site parking, and access to shared amenities such as a swimming pool, deck, patio, and barbecue.
Blueground Shawmut Pool Nr Boston Common Bos-1236 - Boston, MA
No reviews

Blueground Shawmut Pool Nr Boston Common Bos-1236

apartment, Boston
This flat in Boston's South End offers excellent access to Boston South Station and Back Bay, placing you 2.6 kilometres from Boston Common and within walking distance of attractions such as the Freedom Trail and the Boston Tea Party Ship & Museum.
This 66 square metre residence accommodates up to three guests and features a fully equipped kitchen with a microwave oven and dishwasher, air conditioning, complimentary WiFi, an indoor swimming pool, and an on-site sauna.
Stunning Apt With City Views - Boston, MA
No reviews

Stunning Apt With City Views

apartment, Boston
This Boston flat offers a prime downtown location, a 5-minute walk from TD Garden and the Freedom Trail, with Science Park and Haymarket underground stations within 700 meters.
This one-bedroom flat, measuring 53 square meters and accommodating up to three guests, includes air conditioning, Wi-Fi, a fully equipped kitchen, a washing machine and dryer, and on-site access to a swimming pool and fitness centre.
Curated Designer Retreat  Pool  Gym  Dining - Boston, MA
10 22 reviews

Curated Designer Retreat Pool Gym Dining

apartment, Everett
This Everett flat is centrally located, offering convenient access to Encore Boston Harbor (approximately 640 metres) and LEGOLAND Discovery Center (approximately 960 metres).
This 92 square metre residence accommodates up to 5 guests with 6 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, air conditioning, Wi-Fi, a swimming pool, garden, spa, and covered parking, with an 11:00 check-out time.

Frequently asked questions about holiday rentals in Boston, MA

  • What should a first-time visitor not miss in Boston, MA?

    You simply must visit the Freedom Trail, a 4km red brick path winding through 16 historic sites. A must-see is the Boston Tea Party Ships & Museum, where you can experience the famous event firsthand. And don't forget to wander through the bustling Faneuil Hall Marketplace, a historic market with a wide range of shops and restaurants.
  • What are the best Airbnb and vacation rentals in Boston, MA?

  • What kind of vacation rentals are on offer in Boston?

    Stay in a home by the beach, a house with a pool, a downtown condo, or an industrial-chic studio. You'll find all kinds of vacation rentals in Boston to choose from for your next visit.
  • Which neighborhood in Boston, MA should you consider for a vacation rental?

    For a vibrant atmosphere, consider the Back Bay, known for its elegant brownstones and proximity to shops and restaurants. For a more relaxed vibe, try the South End, with its charming Victorian architecture and trendy eateries. If you prefer a quieter stay, Beacon Hill offers a charming, historic setting with cobblestone streets and beautiful gardens.
  • What are the most popular Airbnbs in Boston, MA?

  • What's an unmissable itinerary for a trip to Boston?

    You need a few days to spend in Boston, but if you're short on time, we recommend these must-see stops in your itinerary. Spend the day following the Freedom Trail, a 2.5-mile trail marked with red brick taking you through downtown Boston and past important historical sites that played a significant role in American history. Then if you want to do some shopping, you might want to check out Faneuil Hall Market Place and grab something to eat at Quincy Market in the central building. Other stops on the Freedom Trail worth visiting include the Paul Revere House, a 17th-century home overlooking a pretty cobblestone-clad square, and North End, where you'll find the Old North Church and "Little Italy." Head over to Hanover Street for coffee and a pastry from one of the many cute cafes, and end the day at the Waterfront. If you want, you can also hop on a sunset cruise to give your feet a rest and watch Boston from the water.
  • What are the top family-friendly attractions in Boston, MA?

    The New England Aquarium is a must-visit for families, with its diverse marine life and interactive exhibits. The Boston Children's Museum is a great place for interactive learning, with hands-on exhibits and play areas. For a fun day out, head to the Boston Duck Tours, where you can tour the city by land and water.
  • What are the best vacation rentals with a pool in Boston, MA?

  • What are the best activities to do in Boston?

    Once you're done with the Freedom Trail and the museums, there are few other cool things to do in Boston. Head over to Boston's hottest neighborhood: Seaport District, a hub for young innovators. You can also enjoy the outdoors in the Public Garden and the Charles River Esplanade. Head out to Cambridge and wander around the famous Harvard Campus, quirky museums, and boutiques in the area. If you're a beer lover, Boston is famous for its brews, microbreweries, distilleries, and cider houses, so why not sign up for a tipsy tour around the city?
  • When is the best time to book a vacation rental in Boston, MA?

    To avoid the crowds and get the best deals, book your vacation rental in the shoulder seasons, from April to May or September to October. However, if you're keen on experiencing the city's festive atmosphere, you might prefer to book during the peak season, from June to August.
  • What are the best rentals for families and kids in Boston, MA?

  • What must-see sites are there in Boston?

    Definitely the Freedom Trail; make this your number one must-see site on your sight-seeing agenda. Also, pay a visit to Fenway Park, the Museum of Fine Arts, and the Boston Tea Party Ship & Museum.
  • What events or festivals should visitors check out in and around Boston, MA?

    The Boston Marathon, held annually in April, is a major sporting event. The Boston Calling Music Festival, held in May, features a diverse range of music acts. For a taste of local culture, visit the Boston Harborfest in July, a celebration of the city's maritime history.
  • What are the best rentals or Airbnbs with a jacuzzi in Boston, MA?

    The best vacation rentals or Airbnb with a jacuzzi in Boston, MA are Victorian Condo, Modern - Spacious 1br For 4 - Easy Marathon Access and *Heart Of Boston* Downtown/south End/back Bay.

  • What should you eat in Boston?

    Seafood, seafood, seafood: Boston is the place to come if you want to eat excellent seafood. We recommend one of the local specialties, the "sacred cod," along with other delicious dishes like thick and creamy chowder, freshly steamed lobster, and fresh oysters. If seafood is not to your taste, then don't worry. Head to Chinatown for excellent Asian food or grab a bowl of fresh pasta in the North End.
  • What are the best budget-friendly activities in Boston, MA?

    Take a stroll through the Public Garden, a beautiful oasis in the heart of the city. Explore the free exhibits at the Museum of Fine Arts. Enjoy a picnic lunch at the Boston Common, a historic park with plenty of green space.
  • What are the best restaurants with local dishes in Boston, MA?

    For authentic New England seafood, try the Boston Chowda Company. For a taste of Italian-American cuisine, visit Mike's Pastry. For a truly Boston experience, head to Durgin-Park, a historic restaurant serving classic New England dishes.
  • What are the best walking or cycling routes in Boston, MA?

    The Freedom Trail is a great walking route, taking you past many historical landmarks. The Charles River Esplanade is a beautiful waterfront path perfect for cycling. For a scenic route, try the Minuteman Bikeway, a 25km paved path following the route of the first battle of the American Revolution.
  • Are there pet-friendly attractions in Boston, MA?

    Many parks in Boston are dog-friendly, including the Boston Common and the Public Garden. The Boston Harborwalk is also a great option for a walk with your furry friend. Some restaurants and cafes also welcome dogs on their patios.
  • What are the benefits of choosing a vacation rental in Boston, MA?

    Vacation rentals offer more space and privacy compared to hotels, often with amenities like kitchens and laundry facilities. They can also be more affordable, especially for families or groups travelling together.
  • What are the top sports attractions and facilities in Boston, MA?

    Fenway Park, home to the Boston Red Sox, is a must-visit for any sports fan. The TD Garden hosts the Boston Celtics and the Boston Bruins, while Gillette Stadium is home to the New England Patriots.

Popular destinations

Best Boston, MA holiday rentals with a balcony

3 Mi To Blue Hills Skiing & Hiking! Couples Apt - Boston, MA
10 1 review

3 Mi To Blue Hills Skiing & Hiking! Couples Apt

apartment, Milton
This one-bedroom flat is situated in a quiet suburban area of Milton, 16 kilometres from Boston's city centre, offering convenient access to the Blue Hills Reservation, located 4.8 kilometres away, which provides opportunities for skiing, hiking, and biking.
This 46 square metre apartment, suitable for two guests, features a covered balcony, two Smart TVs, free WiFi, and air conditioning, with shared driveway and street parking available, and is located on the third floor accessible via two flights of stairs.
Vintage 5br Apt In Boston With Free Parking - Boston, MA
9.7 3 reviews

Vintage 5br Apt In Boston With Free Parking

apartment, Boston
This spacious 5-bedroom flat in Boston offers convenient access to Harvard University and Harvard Square, located approximately 4 kilometres away, with Brattle Theatre and Central Square Theatre also within 4 kilometres.
This substantial property boasts 167 square metres of living space, accommodating up to 22 guests with its five bedrooms and two bathrooms, and includes private parking and a balcony.
3 Mi To Blue Hills Skiing & Hiking! Couple’s Apt - Boston, MA
No reviews

3 Mi To Blue Hills Skiing & Hiking! Couple’s Apt

apartment, Milton
This Milton flat provides convenient access to Blue Hills Skiing and Hiking, located 4.8 kilometres away, and is within 11.3 kilometres of Boston landmarks such as the John F. Kennedy Presidential Library and Museum and Back Bay.
This 46-square-metre apartment accommodates up to three guests, featuring a fully equipped kitchen, air conditioning, a balcony, free Wi-Fi, and private parking, with a check-out time of 10:00 AM.
Modern Furnished Apartment In Heart Of Quincy - Boston, MA
8.8 6 reviews

Modern Furnished Apartment In Heart Of Quincy

apartment, Quincy
This modern two-bedroom apartment is located in Quincy, just 11.6 kilometres from the John F. Kennedy Presidential Library and Museum.
The 91 square metre apartment offers a fully equipped kitchen, a terrace, a fitness centre, and free on-site parking, making it ideal for families or groups of up to seven guests.

Best Boston, MA holiday rentals with parking

Spacious 2 Bedrooms Apt -Roof Deck No Cleaning Fee - Boston, MA
9.9 895 reviews

Spacious 2 Bedrooms Apt -Roof Deck No Cleaning Fee

apartment, Cambridge
This spacious Cambridge flat, situated near the Green and Red Line subway stations, offers easy access to Boston and is within 1.6km of various supermarkets including Whole Foods and Trader Joe's.
The 93-square-metre, third-floor property sleeps four, boasting two bedrooms, one bathroom, a private deck, in-unit laundry, and modern furnishings from Crate & Barrel, Pottery Barn, and West Elm; a nearby Saturday farmer's market adds to its appeal.
Apt 2br Quincy Hideout W Balcony, Bathtub, Tv Near Wollaston Beach 74l - Boston, MA
9.7 3 reviews

Apt 2br Quincy Hideout W Balcony, Bathtub, Tv Near Wollaston Beach 74l

apartment, Quincy
This Quincy apartment, situated a short 6.4km drive from Boston's South Station and Back Bay, offers easy access to Wollaston Beach, a 10-minute walk away.
This two-bedroom, one-bathroom flat boasts a spacious 1100 square metre floor area, sleeps up to 18 guests, and includes a fully equipped kitchen, private parking, and a terrace with garden access.
Cozy 3br Boston Apt  Pet-friendly W/ Parking  Red Line & I-93 Access 80/3 - Boston, MA
10 4 reviews

Cozy 3br Boston Apt Pet-friendly W/ Parking Red Line & I-93 Access 80/3

apartment, Boston
This Dorchester, Boston flat is conveniently located near the Shawmut subway station (a 4-minute walk) and offers easy access to the Boston Convention and Exhibition Centre (a 14.5-kilometre drive) and Copley Square (also a 14.5-kilometre drive).
The three-bedroom, one-bathroom property sleeps up to 13 guests, features a fully equipped kitchen including a dishwasher, in-unit laundry, and free on-site parking, alongside air conditioning and Wi-Fi.
Adorable Apartment-longwood/fenway - Boston, MA
9.5 76 reviews

Adorable Apartment-longwood/fenway

apartment, Boston
This Boston studio flat is ideally located in the Longwood Medical Area, less than 1.6 km from Fenway Park and within a kilometre of the Museum of Fine Arts and Isabella Stewart Gardner Museum, offering easy access to the Fenwood Green Line station.
The self-contained apartment sleeps two, features a fully equipped kitchen with appliances including a dishwasher, a comfortable Posturepedic bed, and a flat-screen TV with YouTube TV; a shared launderette is nearby.
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