Holiday Rentals in Boston, MA

10420 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Boston, MA holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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.

Oceanfront Pool. Close To Boston. Free Parking. - Boston, MA
9.9 280 reviews

Oceanfront Pool. Close To Boston. Free Parking.

apartment, Winthrop Town
This one-bedroom apartment is situated in Winthrop Town, just 6.4 kilometres from Boston, offering easy access to the city via public transport. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The apartment is ideal for a couple, with a separate entrance and exclusive use of the space. The apartment offers a range of amenities, including a modern kitchen, air conditioning, a swimming pool, and a garden, ensuring a comfortable and enjoyable stay.
2 Tdgarden Celtics/bruins/lil Italy/historic - Boston, MA
9.0 110 reviews

2 Tdgarden Celtics/bruins/lil Italy/historic

apartment, Boston
This Boston North End studio apartment is situated a short distance from the Old North Church and Freedom Trail, offering easy access to the waterfront and major attractions such as Faneuil Hall Marketplace and TD Garden.
The self-contained apartment, sleeping up to three guests, features a queen-size bed, pull-out sofa bed, full kitchen with induction hob, and a walk-in shower; nearby activities include exploring the historic North End and utilising the nearby MBTA subway stations.
North End 2-story Penthouse / Prime Location - Boston, MA
10 8 reviews

North End 2-story Penthouse / Prime Location

apartment, Boston
This spacious four-bedroom, three-and-a-half-bathroom penthouse apartment is located in Boston's historic North End, adjacent to the Old North Church and within a 700-metre walk of the Paul Revere House and Faneuil Hall.
This family-friendly dwelling accommodates up to ten guests with two master suites, a fully equipped kitchen, and an in-unit washer/dryer, while offering convenient access to public transport from North Station, just 600 metres away.
Waterfront Escape - Spectacular Views, Only 5 Minutes From Boston Airport - Boston, MA
10 2 reviews

Waterfront Escape - Spectacular Views, Only 5 Minutes From Boston Airport

apartment, Boston
This luxurious East Boston apartment, a five-minute drive from Logan International Airport and a fifteen-minute drive from Boston city centre, offers stunning waterfront views and is situated just one block from Constitution Beach.
Sleeping ten guests, this four-bedroom, five-bathroom property boasts a spacious open-plan kitchen and dining area, a terraced garden with fire pit, movie room, top-floor lounge/bar with fireplace, and unique design features including a Japanese futon and high ceilings; free street parking is available.

Best family friendly Boston, MA holiday rentals

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

Panoramic View, Large Deck, Ground Floor Apartment, Walk To Subway And Beach - Boston, MA
9.2 397 reviews

Panoramic View, Large Deck, Ground Floor Apartment, Walk To Subway And Beach

apartment, Boston
This family-friendly flat is situated on Boston's waterfront, close to the University of Massachusetts Boston, Northeastern University, Copley Place, and the Boston Museum of Fine Arts. It has excellent user, location, and cleanliness ratings.
The one-bedroom flat is 49 square metres and has a fully equipped kitchen, a private balcony, and a comfortable living space. Amenities include a swimming pool, a fitness centre, a tennis court, and a garden, offering plenty of options for relaxation and entertainment.
Charming Tree Top Victorian - Two Bedroom Retreat - Boston, MA
10 18 reviews

Charming Tree Top Victorian - Two Bedroom Retreat

apartment, Boston
This family-friendly flat is located in Jamaica Plain, a neighbourhood in Boston, just 3km from Franklin Park Zoo, Brigham and Women's Hospital, and Longwood Medical Area. It has received excellent user ratings, making it a popular choice for travellers.
The apartment is spacious, with 2 bedrooms, 1 bathroom, and a floor area of 149 square metres, comfortably accommodating up to 4 guests. A range of amenities are available, including a swimming pool, tennis court, garden, and barbecue grills, ensuring a relaxing and enjoyable stay.
Charming Alcove Studio With Cozy Hideaway - Inviting Serenity Retreat - Boston, MA
No reviews

Charming Alcove Studio With Cozy Hideaway - Inviting Serenity Retreat

apartment, Boston
This two-bedroom flat is located on the southeastern edge of Back Bay, bordering the South End and across Massachusetts Avenue from Northeastern University, offering easy access to Boston's medical institutions and the Southwest Corridor Park.
This private unit, suitable for two guests, features a kitchen with a fridge and dishwasher, air conditioning, and provides a historical lodging experience within an early 1900s building, with on-site support available.
84 M² Apartment ∙ 2 Bedrooms ∙ 4 Guests - Boston, MA
No reviews

84 M² Apartment ∙ 2 Bedrooms ∙ 4 Guests

apartment, Boston
Apartment to rent for 4 guests. You will be based in Boston.
Facilities and services: a freeze, an iron and a washing machine. Take advantage of the air conditioning in this apartment!

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.

68 M² Apartment ∙ 1 Bedroom ∙ 5 Guests - Boston, MA
No reviews

68 M² Apartment ∙ 1 Bedroom ∙ 5 Guests

apartment, Boston
This two-bedroom, one-bathroom flat is located in Boston's Seaport District, a mere 100 metres from the Institute of Contemporary Art and waterfront paths, with South Station and the Seaport Ferry easily accessible for exploring the city.
This 68-square-metre apartment accommodates up to five guests and features floor-to-ceiling windows, a modern kitchen with stainless steel appliances, an in-unit washer and dryer, and access to a communal swimming pool and fitness centre.
Modern 2br Retreat Minutes From Boston - Boston, MA
9.7 27 reviews

Modern 2br Retreat Minutes From Boston

apartment, Chelsea
This two-bedroom flat in Chelsea offers a convenient base, being just a few minutes from downtown Boston and providing easy access to Logan Airport, with public transport and major motorways also within close proximity.
This Chelsea apartment comfortably sleeps up to seven guests and boasts resort-style amenities including a seasonal outdoor pool, a fitness centre, lounge areas, and a patio, alongside essential features such as air conditioning and a fully equipped kitchen.
Luxury Apartments By Hyatus At Boston Everett - Boston, MA
9.0 6 reviews

Luxury Apartments By Hyatus At Boston Everett

apartment, Everett
This Everett flat offers proximity to key destinations, situated within 4.8 kilometres of Encore Boston Harbor and Assembly Row, with Chelsea Station a 14-minute walk away.
This serviced apartment provides a swimming pool, fitness centre, and rooftop terrace, alongside in-unit laundry and complimentary public area Wi-Fi, with free on-site parking and gas grills for guest convenience.
Stunning Modern 2br 2ba|kind Bed| Assembly Square - Boston, MA
No reviews

Stunning Modern 2br 2ba|kind Bed| Assembly Square

apartment, Somerville
This modern flat is located in Assembly Row, Somerville, offering direct access to dining, cafes, and a cinema, with the nearest amenities within a few hundred metres.
This spacious two-bedroom, two-bathroom apartment accommodates up to six guests and features a fully equipped kitchen, in-unit laundry, air conditioning, a swimming pool, fitness centre, and parking.

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.

25 Cozy 1br-commuter Rail To Salem In 21 Minutes - Boston, MA
9.2 75 reviews

25 Cozy 1br-commuter Rail To Salem In 21 Minutes

apartment, Chelsea
This brand-new, luxurious two-bedroom flat is located in Chelsea, just 6 kilometres from Downtown Boston and a short drive from several hospitals. The property has been rated excellent for cleanliness, location and user experience.
The flat is spacious and offers a living room, a den/office that can be used as a second bedroom, and flexible lease terms. It comes fully furnished with a stocked kitchen, modern amenities like a washer/dryer, fast internet and a TV with Roku streaming, as well as a heated garage and the option for weekly or monthly cleaning services.
Family-friendly 3br Apt - Easy Downtown Boston Accesss - Near Franklin Park 603 - Boston, MA
9.6 27 reviews

Family-friendly 3br Apt - Easy Downtown Boston Accesss - Near Franklin Park 603

apartment, Boston
This spacious Boston apartment, located in Mattapan, offers convenient access to attractions such as Fenway Park and Faneuil Hall Marketplace, though precise distances aren't specified.
The 120 square metre (1300 sq ft) property features three bedrooms sleeping up to 15 guests, a fully equipped kitchen, parking, and amenities including Wi-Fi, a washer/dryer, and a terrace.
Spectacular, Luxury Bay Village/back Bay Condo - Boston, MA
9.6 501 reviews

Spectacular, Luxury Bay Village/back Bay Condo

apartment, Boston
This Bay Village duplex flat is ideally located in Boston, a short walk from Back Bay, the South End, Boston Common, and the Theatre District.
The two-bedroom, one-bathroom apartment, sleeping four, features a fully equipped kitchen, private outdoor space, and on-site parking (suitable for compact cars under 1.83 metres wide); note the spiral staircase.
Central Square Lux Studio 2-queen Beds Mit/harvard - Boston, MA
9.7 35 reviews

Central Square Lux Studio 2-queen Beds Mit/harvard

apartment, Cambridge
This Cambridge studio apartment enjoys a prime Kendall Square location, within 1.6 to 2.4 km of MIT, Harvard Square, and Boston city centre.
The self-contained apartment, sleeping up to four guests in two queen/full beds and two twin-size folding beds, features a fully equipped gourmet kitchen, in-unit laundry, free parking (for monthly stays), a mezzanine terrace with garden access, and free use of a fitness centre and business centre.

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.

Boston Landing Stays - Boston, MA
8.0 109 reviews

Boston Landing Stays

apartment, Boston

Best Boston, MA holiday rentals with a balcony

14-1- 3br Milton -Cozy Apt Near Blue Hills Museum - Boston, MA
10 1 review

14-1- 3br Milton -Cozy Apt Near Blue Hills Museum

apartment, Milton
Modern Beautiful Apartment-5 Beds-full Kitchen-parking-super Clean-great For Groups - Boston, MA
9.3 354 reviews

Modern Beautiful Apartment-5 Beds-full Kitchen-parking-super Clean-great For Groups

apartment, Boston
Cozy 5br Jamaica Plain | Walk To T & Downtown - Boston, MA
10 3 reviews

Cozy 5br Jamaica Plain | Walk To T & Downtown

apartment, Boston
3br2bth Td Garden Bos Mit Harvard 2 Parking Spaces - Boston, MA
9.3 10 reviews

3br2bth Td Garden Bos Mit Harvard 2 Parking Spaces

house, Somerville

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.

Sun-filled 1br Steps From Public Garden - Boston, MA
No reviews

Sun-filled 1br Steps From Public Garden

apartment, Boston
Upscale 4br Penthouse With Gym & Parking Near Mgh & Tufts - Boston, MA
8.0 7 reviews

Upscale 4br Penthouse With Gym & Parking Near Mgh & Tufts

apartment, Boston
Amazing Theatre District Location. Pet Friendly Stays For Short And Long Term - Smart Lock Enabled! - Boston, MA
8.0 1 review

Amazing Theatre District Location. Pet Friendly Stays For Short And Long Term - Smart Lock Enabled!

apartment, Boston
Back Bay Heart 3br 2baa Condo - Boston, MA
9.2 30 reviews

Back Bay Heart 3br 2baa Condo

apartment, 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.

Back Bay Ultra Luxury Studio At Raffles Boston - Boston, MA
10 6 reviews

Back Bay Ultra Luxury Studio At Raffles Boston

apartment, Boston
Brand New Luxury Retreat W/ Pool & Fitness Center - Boston, MA
9.5 4 reviews

Brand New Luxury Retreat W/ Pool & Fitness Center

apartment, Boston
Studio Apt Private Bath+ Free Parking - Boston, MA
9.5 163 reviews

Studio Apt Private Bath+ Free Parking

studio, Cambridge
Cozy Home - Close To Everything - Boston, MA
10 3 reviews

Cozy Home - Close To Everything

apartment, Boston

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.

Historic Townhouse In The Heart Of Boston - Boston, MA
9.7 301 reviews

Historic Townhouse In The Heart Of Boston

apartment, Boston
©2026 cozycozy.com