Holiday Rentals in Boston, MA

10420 available vacation rental offers

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Boston, MA holiday rentals
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Best Holiday rentals and Airbnb offers 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

Modern Comfort - Boston, MA
9.6 5 reviews

Modern Comfort

apartment, Boston
This three-bedroom apartment in Boston, Massachusetts, is conveniently located a short drive (approximately 10km) from the Museum of Fine Arts, Fenway Park, and the Massachusetts Institute of Technology.
The 177 square metre property offers free Wi-Fi, private parking, a fully equipped kitchen, and can comfortably accommodate up to nine guests.
North End Entire House Downtown/td Garden - Boston, MA
9.9 70 reviews

North End Entire House Downtown/td Garden

house, Boston
This three-bedroom Boston apartment, situated in the North End, is a short walk from the TD Garden and within easy reach of the Freedom Trail, Boston Harbour, and other key attractions.
This family-friendly townhouse offers six guests ample space across three en-suite bedrooms, complete with a fully equipped kitchen, in-unit laundry, and modern amenities such as Smart TVs and memory foam mattresses; family-friendly extras like a highchair and travel cot are available on request.
North End/td Garden Condo W/rooftop Deck - Boston, MA
9.8 189 reviews

North End/td Garden Condo W/rooftop Deck

apartment, Boston
This two-room flat is situated in Boston's historic North End, just a short walk from Quincy Market, the Aquarium, and the Greenway. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The flat is ideal for families or groups of friends, with a comfortable layout and a capacity of four guests. Guests can enjoy amenities such as two TVs, wireless internet, a fully equipped kitchen, and a private rooftop deck with stunning city views.
Luxury Boston 2br,back Bay, Pru, Copley, Fenway - Boston, MA
10 52 reviews

Luxury Boston 2br,back Bay, Pru, Copley, Fenway

apartment, Boston
This top-floor flat in Boston's South End is a short walk (less than 1 km) from Back Bay Station and attractions including Copley Square and the Boston Public Garden.
The two-bedroom, one-bathroom apartment sleeps four, offering a fully equipped kitchen, in-unit laundry, fast Wi-Fi, and smart TVs in each bedroom; nearby activities include exploring Newbury Street and the Prudential Center.

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.
3br3bth Penthouse 4 Parking Spaces/td/mit/harvard - Boston, MA
10 82 reviews

3br3bth Penthouse 4 Parking Spaces/td/mit/harvard

apartment, Somerville
This Somerville penthouse loft, a 10-minute walk (1.6 km) from the T station, offers easy access to Boston and is near local amenities.
The three-bedroom, three-bathroom apartment sleeps eight, features a fully equipped kitchen, in-unit laundry, free parking for two cars (including an EV charger), and boasts stunning park and pool views.
Blueground | Downtown, Pool, Nr Boston Common - Boston, MA
No reviews

Blueground | Downtown, Pool, Nr Boston Common

apartment, Boston
This one-bedroom flat is located in Downtown Boston, offering convenient access to Faneuil Hall Marketplace and TD Garden, and is a short distance from Boston Harbor and Flynn Cruiseport Boston.
This 68 square meter residence accommodates two guests and features a fully equipped kitchen, air conditioning, and building amenities including a swimming pool and doorman, with flexible lease options available.
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.

Frequently asked questions about holiday rentals in Boston, MA

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

    You have to see the Freedom Trail, it's a 4km walking path that connects 16 historical sites, including the Boston Common and the Paul Revere House. You should also take a trip to the top of the State House dome for amazing views of the city.
  • 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 lively atmosphere, consider the Back Bay, with its elegant brownstones and proximity to shops and restaurants. For a more relaxed vibe, try Beacon Hill, known for its cobblestone streets and charming houses.
  • 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, and the New England Aquarium is always a hit with kids of all ages. For a bit of history, the Boston Tea Party Ships & Museum is a great option, with interactive exhibits and even a replica ship to explore.
  • 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 prices, book your vacation rental during the shoulder seasons, spring (April-May) or autumn (September-October). You'll still have plenty of sunshine and milder temperatures.
  • 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 in April is a huge event, and the Boston Calling Music Festival in May brings in big-name acts. For something more unique, check out the Boston Harborfest in July, a week-long celebration of the city's maritime history.
  • 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?

    A walk along the Charles River Esplanade is a great way to enjoy the city's natural beauty without spending a penny. You can also visit the Boston Public Garden, a beautiful park with swan boats and a walking path.
  • What are the best restaurants with local dishes in Boston, MA?

    For a taste of New England, try a classic clam chowder at the Union Oyster House, the oldest restaurant in the US. If you're looking for something more modern, check out the Boston Public Market, which features local vendors selling fresh produce and artisan food.
  • What are the best walking or cycling routes in Boston, MA?

    The Freedom Trail is a great walking route, and the Emerald Necklace is a network of parks and gardens that stretches across the city. For cycling, the Charles River Esplanade is a popular choice, with dedicated bike paths.
  • Are there pet-friendly attractions in Boston, MA?

    The Boston Common is a great place to walk your dog, and many of the city's parks are also pet-friendly. The Boston Public Garden even has a dog park.
  • What are the benefits of choosing a vacation rental in Boston, MA?

    Vacation rentals offer more space and privacy than a hotel, and they often come with a kitchen, which allows you to save money on meals. You can also find rentals in different neighbourhoods, giving you a more local experience.
  • What are the top sports attractions and facilities in Boston, MA?

    Fenway Park, home to the Boston Red Sox, is a must-visit for baseball fans. The TD Garden is home to the Boston Celtics and the Boston Bruins, and the Gillette Stadium is home to the New England Patriots.

Popular destinations

Best Boston, MA holiday rentals with a balcony

Cozy 5br Milton Home  Pet-friendly Near I-93 & Blue Hills 14-2 - Boston, MA
9.4 9 reviews

Cozy 5br Milton Home Pet-friendly Near I-93 & Blue Hills 14-2

apartment, Milton
This five-bedroom Milton townhouse, sleeping up to 15 guests (extra fees apply beyond 6), offers easy access to the Blue Hills Reservation and is conveniently located for trips to Boston.
The 168 sq m property boasts three bathrooms, a fully equipped kitchen including a dishwasher, and three reserved parking spaces; self check-in is available.
Hidden Gem In Boston: Long Term 1 Month + Only - Boston, MA
10 2 reviews

Hidden Gem In Boston: Long Term 1 Month + Only

apartment, Boston
This Hyde Park flat is situated 9.6km from Fenway Park and Copley Square, offering a quieter alternative to central Boston, and is also conveniently located within 9.6km of Northeastern University and Franklin Park Zoo.
The three-bedroom, one-bathroom property sleeps four guests and includes in-unit laundry facilities, air conditioning, Wi-Fi, and is pet-friendly.
Cozy 5br Jamaica Plain | Walk To T & Downtown - Boston, MA
10 3 reviews

Cozy 5br Jamaica Plain | Walk To T & Downtown

apartment, Boston
This five-bedroom Jamaica Plain flat, a 1.6km walk from Forest Hills T station, offers easy access to Boston's city centre and proximity to Franklin Park.
Sleeping up to twelve guests, the property features a professionally designed open-plan layout, a fully equipped kitchen with dishwasher, high-speed internet, and a terrace; on-street parking is available at a cost.
Cozy 5br Jamaica Plain | Walk To T & Downtown - Boston, MA
9.0 2 reviews

Cozy 5br Jamaica Plain | Walk To T & Downtown

apartment, Boston
This five-bedroom Jamaica Plain flat is a short walk from the Orange Line subway station, offering easy access to Boston city centre and Franklin Park.
The property boasts a spacious open-plan design, sleeping up to ten guests and including a fully equipped kitchen, high-speed internet, and a terrace; on-street parking is available at a cost.

Neighborhoods and points of interest in Boston, MA

Best Boston, MA holiday rentals with parking

Open-concept 5br Condo | Jamaica Plain & T Walk - Boston, MA
9.4 13 reviews

Open-concept 5br Condo | Jamaica Plain & T Walk

apartment, Boston
This five-bedroom apartment is located in Jamaica Plain, a lively neighbourhood in Boston, just 5 kilometres from the scenic Franklin Park Arboretum. The property has received excellent guest ratings, highlighting its appeal to travellers.
The apartment is ideal for large groups, accommodating up to 12 guests comfortably. It features a fully equipped kitchen, a private terrace, a garden, and a Jacuzzi, alongside other amenities like streaming services and secure keyless entry.
Brand New Luxury Retreat W/ Pool & Fitness Center - Boston, MA
9.8 12 reviews

Brand New Luxury Retreat W/ Pool & Fitness Center

apartment, Boston
This South Boston flat provides modern accommodation with convenient access to Carson Beach, Downtown Boston, and the Red Line, situated less than 500 meters from key transport links.
This two-bedroom residence, accommodating up to six guests, boasts a heated outdoor swimming pool, two fitness centres, a yoga studio, resident lounges, a courtyard with grilling stations, in-suite laundry, and a pet wash station, all within a luxury apartment complex.
Convenient 2 Br Near Bus/train - Boston, MA
9.2 100 reviews

Convenient 2 Br Near Bus/train

apartment, Boston
This two-bedroom apartment, ideally located near the University of Massachusetts Boston, offers easy Red Line access to downtown Boston, Cambridge, Harvard, MIT, and Logan Airport.
The 2-bathroom flat sleeps five guests comfortably, includes in-unit laundry facilities, and is within walking distance of public transport.
Modern Smart 1bdr Private Entry Historic South End - Boston, MA
10 18 reviews

Modern Smart 1bdr Private Entry Historic South End

apartment, Boston
This charming one-bedroom flat is located in Boston's South End neighbourhood, just 1.6 kilometres from Charles Playhouse, Copley Square, and Copley Place. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The 59 square metre flat comfortably accommodates two guests and features a fully equipped kitchen, a washing machine, a cosy fireplace, and a video library. Guests can also enjoy free Wi-Fi, a Smart TV, and on-site parking.
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