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

Charming Historic Studio With Modern Comforts - Tranquil Urban Retreat - Boston, MA
No reviews

Charming Historic Studio With Modern Comforts - Tranquil Urban Retreat

apartment, Boston
This furnished studio apartment is located in Boston's South End, bordering Back Bay, within 800 meters of Northeastern University and offering easy access to numerous hospitals including Longwood Medical Area, Children's Hospital, and Harvard Medical School.
This 264 sqft private micro-studio, suitable for 2 guests, features a full private bathroom, mini fridge, oven, and air conditioning, with direct access to the 4.3 kilometer Southwest Corridor Park for recreation.
Walk To Shops, Convenient Commute, Safe, Sleeps 5 - Boston, MA
9.9 22 reviews

Walk To Shops, Convenient Commute, Safe, Sleeps 5

apartment, Boston
This two-bedroom flat in Boston's West Roxbury district is a 5-minute drive from Fenway Park and a 20-minute drive from Boston Common.
Offering accommodation for up to five guests, this family-friendly property features a kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning and parking.
Waterfront Escape - Close To Airport & Downtown - Boston, MA
9.8 5 reviews

Waterfront Escape - Close To Airport & Downtown

house, Boston
This Boston waterfront property, near Constitution Beach and a 5.5km drive from North Station and TD Garden, offers direct access to the beach and is conveniently located for exploring the city's attractions.
The 242 square metre villa boasts a fully equipped kitchen, four bathrooms, sleeps up to 19 guests, includes free Wi-Fi and on-site parking, and features a private terrace with garden views.
2 Bedroom Boston Condo In Jamaica Plain With Parking - Boston, MA
9.7 165 reviews

2 Bedroom Boston Condo In Jamaica Plain With Parking

apartment, Boston
This Egleston Square Condo is located in Jamaica Plain, a lively neighbourhood just a short distance from the Boston Museum of Fine Arts and Fenway Park. The property boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay. This two-bedroom flat comfortably sleeps five guests, offering a spacious and well-equipped living space. Amenities include a fully-equipped kitchen, a garden, a swimming pool, a tennis court and a spa, as well as access to bicycles, BBQ facilities and baby strollers upon request.

Best Boston, MA holiday rentals with a pool

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

The Watkins : Elevated Cozy  W/d  Amenities - Boston, MA
9.6 117 reviews

The Watkins : Elevated Cozy W/d Amenities

apartment, Boston
This studio apartment is conveniently located just 5km from Boston College and Harvard University, with easy access to public transport via the T, which is a short 5-minute walk away. The surrounding area offers a blend of academic and urban vibes, with plenty of restaurants, shops, and green spaces to explore.
The apartment has one bedroom with a queen-size bed and a fully equipped kitchen, comfortably accommodating up to three guests. Enjoy a range of amenities, including a swimming pool, garden, fitness centre, and parking, as well as access to shared lounges, kitchens, and meeting spaces within the complex.
Blueground | Assembly Square, Pool, Nr Mystic River - Boston, MA
No reviews

Blueground | Assembly Square, Pool, Nr Mystic River

apartment, Somerville
This Somerville flat is located in the Assembly Square district, a 5-minute walk from Assembly Row and its MBTA station, providing convenient access to the Museum of Science and TD Garden.
This property offers air conditioning, a swimming pool, on-site fitness facilities, and a full kitchen with a fridge, microwave, and dishwasher for your comfort and convenience.
The Clark : Aesthetic  Clean  Amenities! - Boston, MA
9.8 90 reviews

The Clark : Aesthetic Clean Amenities!

apartment, Boston
This stylish studio apartment is situated near Boston College and Harvard University, a short 0.8-kilometre walk from the 'T' subway providing easy access to Boston's attractions.
The self-catering flat offers a queen-size bed, a room divider creating a bedroom area, a fully equipped kitchen with dishwasher, in-unit laundry, a 65” SmartTV, and accommodates up to four guests, with access to a shared complex boasting lounges, gyms, and games rooms.
Nantasket Beach Resort - Boston, MA
8.6 101 reviews

Nantasket Beach Resort

resort, Hull
The Nantasket Beach Resort is situated on Nantasket Beach, a short drive from Plymouth and within easy reach of Boston via the commuter ferry. It has received very good ratings for its location, cleanliness, and overall experience.
The hotel has 33 square metres of floor space, offering a comfortable and well-equipped one-bedroom suite with a spa bath, fireplace, and all the amenities you need. The resort offers a range of facilities, including an indoor-outdoor pool, a restaurant, a bar, a fitness centre, and live music on weekends.

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 2 Bed Apartment In Quincy - Boston, MA
9.5 2 reviews

Luxury 2 Bed Apartment In Quincy

apartment, Quincy
This Quincy apartment, 11.7km from the John F. Kennedy Presidential Library and Museum, offers convenient access to major attractions and boasts free private parking.
The 93-square-metre flat features one bedroom, one bathroom, a fully equipped kitchen, a terrace, a fitness centre, and accommodates one guest; table tennis is available on-site.
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.
4br Mid-century Glam Retreat | Near T - Boston, MA
No reviews

4br Mid-century Glam Retreat | Near T

apartment, Boston
This four-bedroom flat in Boston's Jamaica Plain district is a private unit within a triplex, situated 5 minutes on foot from the Franklin Park arboretum and a 15-minute commute from downtown Boston via the Green Street T stop.
This 186 square metre apartment offers accommodation for up to 11 guests, featuring a custom chef's kitchen, a private back porch, air conditioning, internet, and one off-street parking space, with Tempurpedic-quality mattresses and premium linens for comfort.
3br3bth Penthouse 2 Parking Spaces/td/mit/harvard - Boston, MA
10 1 review

3br3bth Penthouse 2 Parking Spaces/td/mit/harvard

apartment, Somerville
This penthouse flat in Somerville provides excellent access to public transport, being a 10-minute walk from Gilman Square, Assembly, and Sullivan Square T stations, and only 500 meters from Stop & Shop.
This spacious 186 square meter apartment offers three bedrooms, three bathrooms, and sleeps up to eight guests, featuring two living areas, a fully equipped kitchen with a large island, air conditioning in every room, Smart TVs, and private parking for four vehicles including an EV charger, with direct views of Foss Park and its open-air pool.

Neighborhoods and points of interest in Boston, MA

Best Boston, MA holiday rentals with parking

Boston Landing Stays - Boston, MA
8.0 108 reviews

Boston Landing Stays

apartment, Boston
This Boston apartment, situated approximately 1.6km from Harvard Square and 3.2km from the Brattle Theatre, offers convenient access to Cambridge and Boston city centre.
The 75 square metre self-catering flat features a fully equipped kitchen, private patio, free Wi-Fi, one bathroom, and parking, sleeping up to [Number of guests needs to be specified, e.g., four people comfortably].
Modern 3br Boston - Prime World Cup 2026 Location - Near Franklin Park 60-2 - Boston, MA
8.2 5 reviews

Modern 3br Boston - Prime World Cup 2026 Location - Near Franklin Park 60-2

apartment, Boston
This three-bedroom Boston apartment, situated approximately 8-11 kilometres from attractions including the John F. Kennedy Presidential Library and Museum, the Museum of Fine Arts, Back Bay, and Fenway Park, offers convenient access to key city landmarks.
The 930 square metre property boasts three spacious bedrooms, two bathrooms, and sleeps up to 29 guests, featuring amenities such as free Wi-Fi, private parking, a fully equipped kitchen with dishwasher, and air conditioning.
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.
Harvard/mit/bu Riverside Studio W/parking - Boston, MA
9.8 398 reviews

Harvard/mit/bu Riverside Studio W/parking

apartment, Cambridge
This charming studio apartment in Cambridge is located just a short walk (less than 1 kilometre) from Harvard Square and Central Square, offering easy access to the city's vibrant cultural scene. The property has received excellent ratings for cleanliness, location, and overall experience.
This self-catering apartment can accommodate up to 5 guests and features a queen loft bed, a full-size sofa bed, and a queen air mattress. The studio also boasts a modern bathroom with a German rain shower, a peaceful backyard, and a parking permit available upon request.