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

Browse Waterfront Holiday Rentals in Boston, MA

Plan a relaxing coastal holiday at seaside holiday rentals in Boston, MA, situated just a short journey from local shores.

Houseboat In Boston Harbor Wifi A/c /Heat  Be Rocked To Sleep - Boston, MA
9.7 368 reviews

Houseboat In Boston Harbor Wifi A/c /Heat Be Rocked To Sleep

houseboat, Boston
This houseboat is located in Charlestown, just a mile from the Charlestown Navy Yard and The Freedom Trail, and within two miles of TD Garden and Boston Harbor. It has received excellent ratings for user experience, location, and cleanliness.
The houseboat has one bedroom and one bathroom, and can comfortably accommodate up to six guests. It features a kitchen with a fridge and microwave, air conditioning, a terrace, a garden, parking, and a spa tub.
Family-friendly 3br  Easy Blue Line Access Near Boston - Boston, MA
10 3 reviews

Family-friendly 3br Easy Blue Line Access Near Boston

apartment, Boston
This East Boston flat offers convenient access to Revere Beach, approximately 8 kilometres away, and Boston Common, just under 5 kilometres distant, placing you within easy reach of the New England Aquarium and Museum of Science.
This three-bedroom flat accommodates up to ten guests and includes amenities such as air conditioning, Wi-Fi, and a hairdryer, with nearby transport links providing access to TD Garden and Fenway Park for sporting events and concerts.
2br/2ba Seaport Ocean View | Skydeck & Prime Spot - Boston, MA
10 1 review

2br/2ba Seaport Ocean View | Skydeck & Prime Spot

apartment, Boston
This two-bedroom flat offers excellent accommodation in Boston's Seaport district, featuring ocean views and situated within 500 meters of dining, shopping, the waterfront, and Seaport attractions.
This premium apartment sleeps up to five guests, boasting a king-sized master bedroom, a second bedroom with a queen bed, a spacious living area with a 65-inch smart TV, and amenities including air conditioning, a gym, and a fully equipped kitchen with a dishwasher.
Cozy/warm Near-commuter Rail, Boston, Airport, Casino And More ! - Boston, MA
9.8 43 reviews

Cozy/warm Near-commuter Rail, Boston, Airport, Casino And More !

apartment, Chelsea
This family-friendly flat is located in Chelsea, a short distance from the beach and within easy reach of Suffolk University and Encore Boston Harbor. It has received excellent user ratings, making it a popular choice for travellers.
The apartment has two bedrooms and can accommodate up to four guests, offering plenty of space for families or groups of friends. Amenities include a fully equipped kitchen, a spa tub, and a terrace, providing everything you need for a comfortable and enjoyable stay.

Best family friendly Boston, MA holiday rentals

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

120 M² Condo ∙ 2 Bedrooms ∙ 4 Guests - Boston, MA
No reviews

120 M² Condo ∙ 2 Bedrooms ∙ 4 Guests

apartment, Boston
Holiday rental listing for 4 people. You will be located in Boston.
Services and facilities: a fridge, an iron and a freeze. This is a family-friendly apartment!
Luxe 3bd Allston - Boston, MA
No reviews

Luxe 3bd Allston

apartment, Boston
This family-friendly Allston flat is conveniently located 2.6 kilometres from Harvard Square and 2.3 kilometres from Harvard University, with John F. Kennedy Park 1.6 kilometres away and Brattle Theatre 2 kilometres distant.
This spacious 138 square metre apartment offers three bedrooms, two bathrooms, air conditioning, complimentary WiFi, and free private parking, accommodating up to 14 guests with a fully equipped kitchen including a fridge, microwave oven, and dishwasher.
Cozy Stay On Historic Mt Auburn 5 Min To Harvard - Boston, MA
8.7 11 reviews

Cozy Stay On Historic Mt Auburn 5 Min To Harvard

apartment, Watertown Town
This two-bedroom house in Watertown Town offers convenient access to Brattle Theatre (3.4 kilometres), Harvard Square (3.4 kilometres), and John F. Kennedy Park (3.5 kilometres).
This family-friendly accommodation provides 30 square metres of floor area, accommodates up to 7 guests, and includes free WiFi, air conditioning, and private parking for two vehicles, with bicycle rental available for exploring the local area.
Central Square 2br Condo Near Harvard  & Mit Spacious Gym & Work - Boston, MA
9.6 7 reviews

Central Square 2br Condo Near Harvard & Mit Spacious Gym & Work

apartment, Cambridge
This three-bedroom Cambridge flat, located in Kendall Square's innovation district, offers easy access to public transport (a 0.25km walk to the nearest T station) and is within 1.6km of MIT and Harvard Square.
The 107 square metre property boasts two bathrooms, a jacuzzi, a private garden, and parking, comfortably sleeping seven guests and including amenities such as a fully equipped kitchen, in-unit laundry, and access to a fitness centre and rooftop terrace.

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 get a real feel for Boston's history. And no trip to Boston is complete without a visit to the Boston Public Garden, a beautiful park with a swan boat ride. It's a lovely spot to relax and enjoy the city.
  • 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 lively atmosphere, consider the Back Bay. It's close to the Public Garden, Newbury Street, and lots of restaurants. If you prefer a quieter neighbourhood, try Beacon Hill. It's charming with cobbled streets and historic houses, and it's close to the State House.
  • 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-see for kids. They have a great variety of marine life, including penguins and sharks. The Boston Children's Museum is also a popular choice, with interactive exhibits that are fun for all ages. And for a bit of history, take a trip to the USS Constitution, a historic warship.
  • 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 your vacation rental well in advance, especially if you're travelling during peak season, which is from May to October. If you're looking for a bargain, try booking outside of these months, but be aware that the weather may be less predictable.
  • 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 in April, and the Boston Calling Music Festival in May is always popular. If you're visiting in the summer, check out the Boston Harborfest, a festival celebrating the city's maritime history. And in the autumn, the Boston Oktoberfest is a great way to celebrate the season.
  • 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?

    The Boston Public Library is a beautiful building and it's free to enter. You can wander around the reading rooms and admire the architecture. The Boston Common is a great place to relax and enjoy the outdoors, and it's completely free. And for a unique experience, take a walk along the Charles River Esplanade, a scenic walkway with views of the city.
  • What are the best walking or cycling routes in Boston, MA?

    The Freedom Trail is a great walking route, taking you through the city's historical heart. For a more scenic walk, try the Charles River Esplanade. It's a 5.6km walkway along the Charles River, with views of the city and the Boston University Bridge. If you're feeling energetic, you can cycle the Minuteman Bikeway, a 25km path that follows the route of the British troops during the Battle of Lexington and Concord.
  • Are there pet-friendly attractions in Boston, MA?

    Yes, there are plenty of pet-friendly attractions in Boston. The Boston Public Garden is dog-friendly, and there are dog parks throughout the city. Many restaurants and shops welcome dogs, so you can bring your furry friend along for the day.
  • What are the benefits of choosing a vacation rental in Boston, MA?

    Vacation rentals offer more space than a hotel room, and you'll have access to a kitchen, so you can save money on meals. You'll also have more privacy and flexibility, as you can come and go as you please. And some rentals offer unique features, like a balcony or a fireplace, which you wouldn't find in a hotel.
  • What are the top sports attractions and facilities in Boston, MA?

    Boston is a huge sports city, home to the Boston Red Sox (baseball), the Boston Celtics (basketball), the Boston Bruins (ice hockey), and the New England Patriots (American football). You can catch a game at Fenway Park, TD Garden, or Gillette Stadium. There's also the Boston Marathon, which is held every year in April.

Popular destinations

Find the Best Holiday Rentals with a Pool in Boston, MA

Our holiday rentals near the water in Boston, MA include a pool, so a relaxing swim is always on the cards.

Apt In Downtown Seaport With Pool And Gym - Boston, MA
No reviews

Apt In Downtown Seaport With Pool And Gym

apartment, Boston
This one-bedroom flat is located in Boston's Seaport district, a 10-minute walk from Boston Harbor and Flynn Cruiseport Boston, with Faneuil Hall Marketplace and Newbury Street approximately 1.6 kilometres away.
This 59 square metre apartment accommodates up to three guests and offers a fridge, microwave, dishwasher, air conditioning, and a communal swimming pool, with the MBTA Silver Line at Courthouse and South Station providing convenient access to downtown and Logan Airport.
Luxe Revere Studio W/ Lounge, Game Room, W/d, A/c, By Blueground - Boston, MA
No reviews

Luxe Revere Studio W/ Lounge, Game Room, W/d, A/c, By Blueground

studio, Revere
This Revere apartment, situated 1.3 kilometres from Revere Beach and a 2-minute walk from Beachmont Station, offers easy access to public transport and the coast.
The 37-square-metre flat includes a fully equipped kitchen, in-unit laundry, and accommodates two guests, with on-site amenities such as a fitness centre, swimming pool and barbecue facilities.
The Hunter: Comfortable  Bright  Amenities! - Boston, MA
9.7 58 reviews

The Hunter: Comfortable Bright Amenities!

apartment, Boston
This two-bedroom Boston apartment, ideally located near Boston College and Harvard University, is a short 0.8 km walk from the T subway, providing easy access to the city.
The 2-bathroom flat offers two queen beds, sleeping up to five guests, and boasts amenities including a fully equipped kitchen, in-unit laundry, and access to a complex with a swimming pool, fitness centre, and games room; plus, blazing-fast Wi-Fi.
Stylish Apt Downtown Seaport - Boston, MA
No reviews

Stylish Apt Downtown Seaport

apartment, Boston
This Seaport district flat is located 1.6 kilometres from the Old State House and a 17-minute walk from Custom House.
This 68-square-metre apartment accommodates up to seven guests with a fully equipped kitchen, air conditioning, and on-site access to a swimming pool and fitness centre, offering convenient proximity to the Boston Convention and Exhibition Centre and Logan Airport, 6 kilometres away.

Neighborhoods and points of interest in Boston, MA

Our Favourite Holiday Rentals with Parking in Boston, MA

On-site parking takes one thing off your list when visiting Boston, MA, and these holiday rentals have it included.

Luxurious 2br - 2ba Apt At Hyatus - Boston, MA
9.6 26 reviews

Luxurious 2br - 2ba Apt At Hyatus

apartment, Somerville
This Somerville apartment, ideally located near Davis Square, Union Square, and Assembly Row, offers easy access to the Orange Line and is within walking distance of numerous shops and restaurants.
The 93 square metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes amenities such as a swimming pool, spa, and secure parking; the building also features a fitness centre and co-working spaces.
*New* 3 Br South End Duplex With A/c In The City! - Boston, MA
10 189 reviews

*New* 3 Br South End Duplex With A/c In The City!

apartment, Boston
This Boston penthouse duplex, situated in the South End, is within easy walking distance of Newbury Street, Beacon Hill, and the Boston Public Garden.
The three-bedroom, one-bathroom apartment sleeps eight guests and boasts a fully equipped kitchen, in-unit laundry, and a spacious living area with skylights and smart TV; private access to the top two floors offers ample space and privacy.
Harmony Medical Suites Chinatown - Boston, MA
8.2 130 reviews

Harmony Medical Suites Chinatown

studio, Boston
This Boston flat is situated in Chinatown, offering convenient access to the city centre within 700 metres, a six-minute walk to Boston South Station and the Freedom Trail, and an eleven-minute walk to the Boston Tea Party Ship & Museum.
This apartment provides air-conditioned accommodation with complimentary WiFi, a kitchen equipped with a fridge, microwave, and dishwasher, and on-site fitness facilities, with parking also available.
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.

Discover 5-Star Self-Catering Rentals in Boston, MA

Comfort, quality and a prime location; each luxury holiday rental or Airbnb in Boston, MA is selected with your relaxation in mind.

Cozy Longwood-fenway Studio - Boston, MA
9.5 107 reviews

Cozy Longwood-fenway Studio

apartment, Boston

Best Boston, MA holiday rentals with a balcony

The Boiler Room - Close To Subway & Downtown - Boston, MA
9.8 755 reviews

The Boiler Room - Close To Subway & Downtown

apartment, Boston
Airport Subway Condo - Boston, MA
9.3 14 reviews

Airport Subway Condo

apartment, Boston
Unique & Peaceful Boston Home, Ideal For 2026 World Cup Visitor, Free Parking - Boston, MA
9.4 86 reviews

Unique & Peaceful Boston Home, Ideal For 2026 World Cup Visitor, Free Parking

apartment, Boston
Paradise Found: Luxury Roof Deck - Boston, MA
10 9 reviews

Paradise Found: Luxury Roof Deck

houseboat, Boston

Best Pet-Friendly Holiday Rentals in Boston, MA

These dog-friendly holiday rentals and Airbnbs in Boston, MA guarantee a holiday your pet will enjoy as much as you.

Luxurious 1br In Fidi Boston Close To Everything - Boston, MA
8.8 8 reviews

Luxurious 1br In Fidi Boston Close To Everything

apartment, Boston
Downtown Xing | Lots Of Light | Monthly Discounts - Boston, MA
9.4 228 reviews

Downtown Xing | Lots Of Light | Monthly Discounts

apartment, Boston
High End Apt Seaport With Pool - Boston, MA
No reviews

High End Apt Seaport With Pool

apartment, Boston
Hot Tub And Backyard Oasis - Stunning South Boston Escape - Boston, MA
No reviews

Hot Tub And Backyard Oasis - Stunning South Boston Escape

house, Boston

Search Holiday Rentals with a Hot Tub in Boston, MA

Coming home to a hot tub after a day by the water changes the whole feel of a stay. These holiday rentals are ready for you.

Fifa World Cup Stay! Luxury 6,000 Sq Ft Home Near Boston - Boston, MA
9.4 82 reviews

Fifa World Cup Stay! Luxury 6,000 Sq Ft Home Near Boston

apartment, Newton
Convenient 3 Bed - Steps To Kendall - Boston, MA
No reviews

Convenient 3 Bed - Steps To Kendall

apartment, Cambridge
Modern 2 Bedroom 2 Bath Apartment In Heart Of Quincy - Boston, MA
9.0 17 reviews

Modern 2 Bedroom 2 Bath Apartment In Heart Of Quincy

apartment, Quincy
New Luxury 4br/3 Bath Apt W/ac & Ev Charger - Boston, MA
9.9 16 reviews

New Luxury 4br/3 Bath Apt W/ac & Ev Charger

apartment, Somerville

Top-Rated Holiday Rentals with a Spa in Boston, MA

After enjoying everything Boston, MA has to offer, a spa session at your holiday rental is the ideal way to finish the day.

Modern 3br Boston Nest  Pet-friendly  Franklin Park & Red Line 558-2 - Boston, MA
10 21 reviews

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

apartment, Boston