Holiday Rentals in Boston, MA

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Boston, MA holiday rentals
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10420 Holiday Rentals and Airbnb in Boston, MA

Best family friendly Boston, MA holiday rentals

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

Chinatown Central Upscale Condo W/pool & Parking - Boston, MA
9.5 4 reviews

Chinatown Central Upscale Condo W/pool & Parking

apartment, Boston
This three-bedroom Boston flat, near Boston Common and Public Garden, offers easy access to the Back Bay, Tufts Medical Centre, and Logan International Airport.
The property sleeps six (with potential for more at an extra cost), boasts a fully equipped kitchen, en-suite bathrooms, a shared rooftop BBQ area, and access to a building swimming pool, fitness centre, and parking.
2 Bdrm Apt W/ Tower In Jp Victorian - Boston, MA
9.9 541 reviews

2 Bdrm Apt W/ Tower In Jp Victorian

apartment, Boston
This Jamaica Plain flat, close to Franklin Park in Boston, offers easy access to the park's amenities and trails.
The two-bedroom, one-bathroom apartment sleeps four, features a fully equipped kitchen with dishwasher, in-unit laundry, and a shared garden, plus baby equipment is available.
Modern Red Door Haven +5mins To Boston - Boston, MA
9.6 7 reviews

Modern Red Door Haven +5mins To Boston

apartment, Milton
This family-friendly apartment in Milton is situated approximately 10 kilometres from Boston's Museum of Fine Arts and the JFK Presidential Library & Museum, with convenient access to Fenway Park and Back Bay Station.
This expansive 177 square metre flat offers three bedrooms, two bathrooms, and accommodates up to eleven guests, featuring a fully equipped kitchen, complimentary WiFi, air conditioning, and a balcony, with nearby entertainment including an ice-skating rink.
Parking - Private Entrance - King Beds - Boston, MA
9.9 232 reviews

Parking - Private Entrance - King Beds

apartment, Boston
This family-friendly Boston apartment, ideally located in Back Bay, is a 9-minute walk from the Hynes Convention Centre, a 19-minute walk (1.5km) from Fenway Park, and within 1.9km of Boston city centre.
The 84 square metre dwelling boasts two king-size bedrooms, a fully equipped kitchen, private parking (a rarity in Boston), and a private entrance; on-site amenities include a children's playground and laundry facilities are available for longer stays.

Best Boston, MA holiday rentals with a pool

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

58 M² Apartment ∙ 1 Bedroom ∙ 3 Guests - Boston, MA
No reviews

58 M² Apartment ∙ 1 Bedroom ∙ 3 Guests

apartment, Boston
This flat is located in Boston's Seaport district, offering waterfront living with convenient access to downtown Boston and Logan International Airport via the MBTA Silver Line, with the MBTA Silver Line at Courthouse 100 metres away and South Station within walking distance.
This 58 square metre, one-bedroom flat accommodates up to three guests and features a fridge, microwave, dishwasher, air conditioning, and access to a swimming pool and fitness centre.
Lux 1br W/ Amenities In Seaport - Boston, MA
9.5 12 reviews

Lux 1br W/ Amenities In Seaport

resort, Boston
This Seaport District flat in Boston offers easy access to over 100 restaurants and bars, plus numerous cultural attractions.
The one-bedroom, one-bathroom apartment sleeps three, includes a fully equipped kitchen, in-building amenities such as a swimming pool and fitness centre, and provides starter supplies; pet-friendly (with restrictions and fees apply).
Luxury 2br Cambridge | Pool + Parking - Boston, MA
No reviews

Luxury 2br Cambridge | Pool + Parking

apartment, Cambridge
This 2-bedroom flat in East Cambridge offers proximity to Harvard University and MIT, with the Charles River just 400 metres away and cultural sites such as the Berklee College of Music and the Boston Museum of Fine Arts within easy reach.
This modern accommodation, suitable for up to 5 guests, includes parking and air conditioning, with convenient access to Faneuil Hall Marketplace, Fenway Park, and TD Garden for entertainment and sporting events.
Blueground | Prudential, Pool & W/d, Nr Plaza - Boston, MA
No reviews

Blueground | Prudential, Pool & W/d, Nr Plaza

apartment, Boston
This two-bedroom apartment is located in Boston's Back Bay, specifically the Prudential/St. Botolph neighbourhood, offering easy access to the Museum of Fine Arts and other attractions.
The 97-square-metre (1,044-square-foot) flat features two bathrooms, sleeps four guests, and includes a fully equipped kitchen, in-apartment laundry, a swimming pool, and a gym within the building.

Frequently asked questions about holiday rentals in Boston, MA

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

    You've got to see the Freedom Trail, it's a 4km walking route that takes you past 16 historical sites. You'll also want to visit the Boston Public Garden, a beautiful green space in the heart of the city. And of course, no trip to Boston is complete without a visit to Fenway Park, home of the Boston Red Sox.
  • What are the best Airbnb and holiday 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, choose the Back Bay. It's full of shops, restaurants, and historic architecture. If you're looking for a quieter stay, consider Beacon Hill. It's known for its cobblestone streets and charming townhouses.
  • 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 Boston Children's Museum is a must-visit for families with young children. It's a great place to learn through play. The New England Aquarium is also popular with families, with its diverse range of marine life. For a bit of outdoor fun, head to the Boston Common, a large park in the heart of the city.
  • What are the best holiday 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?

    You'll want to book early if you're planning to visit during peak season, which is from late spring to early autumn. If you're on a budget, consider visiting in the shoulder seasons, from April to May or September to October, when prices are typically lower.
  • 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 is a huge event held every April. If you're a fan of music, the Boston Calling Music Festival takes place in May. And for a taste of local culture, head to the Boston Harborfest in July.
  • What are the best rentals or Airbnbs with a jacuzzi in Boston, MA?

  • 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?

    Walking the Freedom Trail is a great way to see the city's historical landmarks without spending a penny. The Boston Public Garden is another free attraction, offering a beautiful escape from the city bustle. And for a unique experience, take a free walking tour with the Boston By Foot organisation.
  • What are the best restaurants with local dishes in Boston, MA?

    For a taste of New England seafood, try the Boston Chowda House. If you're looking for a more casual dining experience, head to the Quincy Market, where you'll find a variety of food stalls serving local favourites. For a truly authentic experience, try the Durgin-Park Restaurant, which has been serving traditional New England fare since 1827.
  • What are the best walking or cycling routes in Boston, MA?

    The Charles River Esplanade is a popular spot for both walking and cycling, offering scenic views of the city. The Freedom Trail is also a great walking route, taking you past many of Boston's historical landmarks. For a more challenging ride, try the Minuteman Bikeway, a 22.5km paved path that follows the route of the historic Minute Man National Historical Park.
  • Are there pet-friendly attractions in Boston, MA?

    The Boston Public Garden is a great place to walk your dog, and many of the city's parks are also pet-friendly. The Boston Common is a large park in the heart of the city, and it's a popular spot for dog walkers. For a unique experience, take your dog to the Boston Dog Party, a monthly event held at various locations around the city.
  • What are the benefits of choosing a vacation rental in Boston, MA?

    Vacation rentals often offer more space and privacy than hotels. They're also a great option for families or groups of friends travelling together. And you can often find vacation rentals in more convenient locations than hotels, especially if you're looking to be close to a particular attraction.
  • What are the top sports attractions and facilities in Boston, MA?

    Fenway Park is home to the Boston Red Sox, one of the most popular baseball teams in the US. The TD Garden is home to the Boston Celtics and the Boston Bruins. The Gillette Stadium is home to the New England Patriots, a professional American football team.

Popular destinations

Best Boston, MA holiday rentals with a balcony

Luxury 2br Apartment With Pool, Balcony & Parking - Boston, MA
9.4 10 reviews

Luxury 2br Apartment With Pool, Balcony & Parking

apartment, Cambridge
This Cambridge apartment, ideally situated 1.9km from Old North Church and a 17-minute walk from Cambridge College, offers easy access to Boston's North Station, TD Garden, and Beacon Hill.
The 88-square-metre property boasts two bedrooms, two bathrooms, accommodates up to nine guests, and includes a fully equipped kitchen, swimming pool, fitness centre, and terrace; nearby recreational facilities include billiards and bike rentals.
Skyline Views And Cozy Reading Nook - Luxurious Multi-floor Retreat - Boston, MA
No reviews

Skyline Views And Cozy Reading Nook - Luxurious Multi-floor Retreat

apartment, Boston
This two-bedroom flat is situated in Boston's Fenway district, offering easy access to local amenities and attractions, with the Fenway Park just 700 meters away.
This multi-level penthouse accommodates up to four guests and features a rooftop deck with skyline and river views, a fully equipped kitchen, and complimentary pack-n-plays for families.
Nantasket Beach Resort - One King Ocean View - Boston, MA
8.8 1479 reviews

Nantasket Beach Resort - One King Ocean View

B&B, Hull
The Nantasket Beach Resort is situated in Hull's city centre, just a 10-minute walk from Nantasket Beach Reservation and Nantasket Beach. The resort has received very good user ratings, with excellent ratings for location and cleanliness.
The hotel has a single bedroom and bathroom, with a floor area of 23 square metres. Guests can enjoy a range of amenities including swimming pools, a fitness centre, a restaurant and bar, and a business centre.
Stylish Roof Deck And Historic Charm - Elegant Fenway Getaway - Boston, MA
No reviews

Stylish Roof Deck And Historic Charm - Elegant Fenway Getaway

apartment, Boston
This four-bedroom flat is located in Boston's Fenway district, a 5-minute walk from Fenway Park and within an 8-minute walk of Back Bay, Brookline, The Fens, and the Charles River Esplanade.
This top-floor unit in a historic building offers a roof deck with views of the Citgo sign and accommodates up to eight guests, with a dog-friendly option available for an additional fee.

Neighborhoods and points of interest in Boston, MA

Best Boston, MA holiday rentals with parking

Modern 3br Boston Nest  Pet-friendly  Franklin Park & Red Line 558-2 - Boston, MA
9.8 22 reviews

Modern 3br Boston Nest Pet-friendly Franklin Park & Red Line 558-2

apartment, Boston
This three-bedroom Dorchester apartment, conveniently located near Boston Harbour and Long Wharf, offers easy access to Fenway Park and the New England Aquarium, all within a reasonable driving distance.
Sleeping up to 13 guests (with extra fees after 6), this self-catering property boasts two bathrooms, a fully equipped kitchen including a dishwasher, free Wi-Fi, air conditioning, reserved parking, and pet-friendly accommodation.
74l - 2br Quincy - Cozy Couple Hideout Near Wollaston Beach - Boston, MA
9.7 3 reviews

74l - 2br Quincy - Cozy Couple Hideout Near Wollaston Beach

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.
Luxury 3brm/1bath Duplex In Jp - Boston, MA
9.9 41 reviews

Luxury 3brm/1bath Duplex In Jp

apartment, Boston
This Jamaica Plain three-bedroom duplex, ideally located in Boston, offers easy access to nearby train lines for exploring the city.
The 3-bedroom apartment sleeps eight, boasting a king and two queen beds plus a queen-size sofa bed, a fully equipped kitchen with dishwasher, air conditioning, parking, and a private backyard; it is surrounded by restaurants and family-friendly attractions.
Amazing Location Studio Parking - Boston, MA
9.6 67 reviews

Amazing Location Studio Parking

studio, Boston
This studio apartment is located in the heart of downtown Boston, just 1.6km from the Old State House and 0.8km from the Custom House, offering easy access to the city's main attractions. It has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The self-catering apartment has a private entrance and a fully equipped kitchen with a microwave and toaster. Guests can enjoy free Wi-Fi, air conditioning, a flat-screen TV, and private parking, making it a comfortable and convenient base for exploring Boston.
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