Holiday Rentals in Massachusetts

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Massachusetts holiday rentals
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41544 Holiday rentals and Airbnb in Massachusetts

Best family friendly Massachusetts holiday rentals

Among the 41544 accommodations in Massachusetts, here are the 4 best family friendly rentals

Little Dipper Retreat Lakefront Cottage, Sunsets & Kayaks! - Massachusetts
10 86 reviews
Massachusetts
19/07 – 24/07
327 â‚¬/nighttotal: 1635 â‚¬ (5 )

Little Dipper Retreat Lakefront Cottage, Sunsets & Kayaks!

2 4
cottage , Holland
This charming beach house is located in Holland, within a 15 km radius of St. Anne's Shrine, Westville Recreation Area, and Old Sturbridge Village, offering easy access to historical attractions and natural beauty. The cottage has received excellent user ratings, indicating a positive experience for previous guests.
The property spans 74 square metres and features two bedrooms, comfortably accommodating up to six guests. The cottage offers a range of amenities, including a well-equipped kitchen, a private terrace, and a garden, perfect for relaxing and enjoying the outdoors.
2 Bedroom 1st Floor Apartment In Savin Hill - Massachusetts
9.8 683 reviews
Massachusetts
16/07 – 18/07
210 â‚¬/nighttotal: 420 â‚¬ (2 )

2 Bedroom 1st Floor Apartment In Savin Hill

1 3
apartment , Boston
This two-bedroom apartment, ideal for families or groups of up to four, is situated in a coastal town near Boston, Massachusetts, approximately 32 kilometres from the city centre and close to Massachusetts General Hospital and the Longwood Medical Area.
The self-contained flat offers a fully equipped kitchen, private garden, off-street parking, and is within easy reach of a harbourside walking and cycling path; guests can enjoy the blend of seaside access and proximity to Boston's attractions.
Elegant Oasis With Pool And Gym - Massachusetts
10 9 reviews
Massachusetts
19/07 – 17/10
197 â‚¬/nighttotal: 17730 â‚¬ (90 )

Elegant Oasis With Pool And Gym

2 1
apartment , Everett
This Everett apartment, conveniently located near Encore Boston Harbour (a 4-minute drive) and Assembly Row (a 6-minute drive), offers easy access to Chelsea station (a 14-minute walk).
The 93-square-metre (1000 square foot) self-catering property features two bedrooms, one bathroom, sleeps six, and includes a swimming pool, spa, garden, parking, and in-unit amenities such as a dishwasher, microwave, and laundry facilities.
Charming Apt -2 Bedroom -Close To Beach/sleeps 6 - Massachusetts
9.6 317 reviews
Massachusetts
07/01 – 12/01
137 â‚¬/nighttotal: 685 â‚¬ (5 )

Charming Apt -2 Bedroom -Close To Beach/sleeps 6

2 2
apartment , Ipswich
This two-bedroom apartment in Ipswich's historic district is a short walk from the River Orwell and the Ipswich railway station, providing easy access to the town centre and surrounding areas.
The 93 square metre flat features a fully equipped kitchen, a large screen TV, a garden and parking, and can accommodate up to six guests.

Top cities

Best pet friendly Massachusetts holiday rentals

Among the 41544 accommodations in Massachusetts, here are the 4 best pet friendly rentals

Updated Stoughton Apartment With Shared Yard! - Massachusetts
9.3 14 reviews
Massachusetts
24/07 – 27/07
186 â‚¬/nighttotal: 558 â‚¬ (3 )

Updated Stoughton Apartment With Shared Yard!

1 2
apartment , Stoughton
This Stoughton apartment, situated approximately 27-32 kilometres from Boston attractions including Fenway Park, the Hynes Convention Centre, and the Museum of Fine Arts, offers easy access to city amenities whilst maintaining a tranquil suburban setting.
The 111 square metre self-catering property features one bedroom, one bathroom, a fully equipped kitchen with dishwasher, in-unit laundry, free Wi-Fi, a fireplace, and shared yard access; ideal for a family or couple seeking a comfortable Stoughton base.
Theater District Cozy 1 Br - Massachusetts
9.1 8 reviews
Massachusetts
31/08 – 07/09
207 â‚¬/nighttotal: 1449 â‚¬ (7 )

Theater District Cozy 1 Br

1 2
apartment , Boston
This Boston Theatre District flat is ideally located a short walk from Boston Common and within 1.6km of the Boston Tea Party Ships & Museum, offering easy access to historical landmarks such as King's Chapel and the Freedom Trail.
This 55 square metre self-catering apartment sleeps three, features a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, and free Wi-Fi.
Modern & Cozy Suite - Massachusetts
Massachusetts
03/07 – 05/07
166 â‚¬/nighttotal: 332 â‚¬ (2 )

Modern & Cozy Suite

2 2
apartment , Norwood
This Norwood flat is located 22.5 to 25.7 kilometres from Boston's key attractions, including Boston University and Fenway Park, with Norwood Memorial Airport a mere 1.9 kilometres away.
This 69.7 square metre apartment accommodates up to seven guests and offers free WiFi, private parking, and a fully equipped kitchen with a dishwasher and oven.
Tahiti*sleeps 5*near Beach*fire Pit*outdoor Shower*grill - Massachusetts
10 11 reviews
Massachusetts
07/01 – 12/01
206 â‚¬/nighttotal: 1030 â‚¬ (5 )

Tahiti*sleeps 5*near Beach*fire Pit*outdoor Shower*grill

1 2
apartment , Plymouth
This Plymouth seaside property, near Priscilla Beach Theatre and White Horse Beach (both within 1.6km), offers stunning ocean views and is 5km from Manomet Beach.
The 51-square-metre house features one bedroom, one bathroom, sleeps five, and includes a fully equipped kitchen, terrace, garden, parking, and Wi-Fi.

Frequently asked questions about holiday rentals in Massachusetts

  • What are the must-see sights in Massachusetts?

    Massachusetts boasts a wealth of historical and cultural attractions. For history buffs, a visit to Boston is essential, exploring sites like the Freedom Trail, Faneuil Hall, and the Boston Tea Party Ships & Museum. Outside of Boston, Plymouth's Plimoth Patuxet Museums offer a glimpse into early colonial life. Salem's maritime history and connection to the Salem Witch Trials are captivating, with sites like the Salem Witch Museum and the Witch History Museum. For a different perspective, consider the John F. Kennedy Presidential Library and Museum in Boston.
  • What are the best Airbnb and holiday rentals in Massachusetts?

    Near Boston Historic Two-bedroom With Modern Amenities, Luxurious Renovated House and Your Home For The Holidays are the most popular Airbnb and holiday rentals in Massachusetts among travellers.

  • Are there unique natural phenomena in Massachusetts?

    While Massachusetts doesn't have dramatic geological features like geysers, its natural beauty is undeniable. The coastline offers stunning views and diverse ecosystems, from the rocky shores of Cape Cod to the sandy beaches of Nantucket and Martha's Vineyard. The Berkshires region provides opportunities for hiking and exploring stunning forests and mountains. The changing colours of autumn foliage are a significant draw for many visitors.
  • What are the most popular Airbnbs in Massachusetts?

  • What essentials should you bring along for a trip to Massachusetts?

    Packing for Massachusetts depends on the time of year. Comfortable walking shoes are a must, as exploring many historical sites and towns involves a lot of walking. Layers are crucial, as the weather can be unpredictable, especially near the coast. In the colder months, pack warm clothing, including a waterproof jacket. Sunscreen and insect repellent are recommended, regardless of the season. Don't forget a reusable water bottle to stay hydrated.
  • What are the best holiday rentals with a pool in Massachusetts?

  • What famous events or festivals are happening in Massachusetts?

    Massachusetts hosts numerous events throughout the year. The Boston Marathon is a world-renowned event held annually in April. The Boston Harborfest, a multi-day celebration of Boston's history and maritime heritage, typically takes place in early July. Many towns and cities have their own local festivals and events, often celebrating local produce or cultural traditions. Check local listings closer to your travel dates for specific events.
  • What are the best rentals for families and kids in Massachusetts?

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Massachusetts?

    A daily budget in Massachusetts can vary greatly depending on your travel style. Accommodation can range from budget-friendly hostels to luxurious hotels. Food costs can be managed by eating at local eateries or preparing some meals yourself. Public transport is available in Boston and some other cities, but car hire might be necessary for exploring the wider state. A reasonable daily budget could range from £100 to £300 per person, but this is just an estimate.
  • What are the best rentals or Airbnbs with a jacuzzi in Massachusetts?

  • Where can you find the best restaurants serving local dishes in Massachusetts, and what are the must-try specialties?

    Massachusetts has a diverse culinary scene. In Boston, you'll find numerous restaurants serving fresh seafood, a regional specialty. Look for clam chowder, lobster rolls, and Boston baked beans. Many restaurants across the state showcase locally sourced ingredients and New England-style cuisine. Exploring different neighbourhoods will reveal hidden gems and local favourites. The North End in Boston is known for its Italian-American restaurants.
  • What are some less-famous attractions in Massachusetts that are worth a visit?

    Beyond the well-known sites, Massachusetts offers many hidden gems. The charming towns of the Berkshires, such as Lenox and Stockbridge, offer beautiful scenery and cultural attractions. The Plimoth Patuxet Museums, while popular, often get overlooked for their depth and detail. Exploring the islands of Martha's Vineyard and Nantucket provides a unique experience beyond the typical tourist trail. The Mount Greylock State Reservation offers stunning views from the highest point in Massachusetts.
  • What are the best activities for engaging with locals and understanding their culture in Massachusetts?

    Visiting local farmers' markets is a great way to interact with residents and sample regional produce. Attending smaller, local festivals and events offers a chance to experience community spirit. Exploring different neighbourhoods beyond the main tourist areas provides a more authentic feel. Striking up conversations with people in local shops or cafes can be a rewarding way to learn about the local culture. Consider taking a guided walking tour focusing on specific neighbourhoods or historical aspects.
  • What unique natural landscapes and terrain features can travellers explore in Massachusetts?

    Massachusetts offers a diverse range of landscapes. The coastline, with its rocky cliffs, sandy beaches, and estuaries, is a significant feature. The Berkshires region provides opportunities for hiking and exploring mountainous terrain. Cape Cod's unique geography, formed by glacial activity, is fascinating. The state's many forests and wetlands offer diverse ecosystems for exploration. Consider visiting the Cape Cod National Seashore or the Berkshire Scenic Railway Museum for unique experiences.
  • How many days are ideal for a trip to Massachusetts, and what are some itinerary suggestions?

    The ideal length of a trip to Massachusetts depends on your interests. A long weekend could focus on Boston and its surrounding areas. A week would allow for exploring Boston thoroughly and venturing to other regions like Cape Cod or the Berkshires. Two weeks would offer ample time for a more comprehensive exploration of the state. Possible itineraries could focus on historical sites, coastal exploration, or outdoor activities in the Berkshires, depending on your preferences.

Nearby regions

Best Massachusetts holiday rentals with a pool

Among the 41544 accommodations in Massachusetts, here are the 4 best rentals with a pool

Sleeps 15  Pool  World Cup 2026  Retreat - Massachusetts
10 34 reviews
Massachusetts
06/07 – 08/07
1313 â‚¬/nighttotal: 2626 â‚¬ (2 )

Sleeps 15 Pool World Cup 2026 Retreat

4 2
apartment , Brimfield
Abigail's Nest, a spacious farmhouse-style property in Brimfield, Massachusetts, is located minutes from Sturbridge and the Brimfield Flea Market.
This 279-square-metre (2997 sq ft) holiday home boasts four bedrooms, three bathrooms, and can accommodate up to fifteen guests, featuring a large kitchen, swimming pool, terrace, garden, and parking.
The Dazzling Two-bedroom Two-bath Suite In Boston - Massachusetts
Massachusetts
03/07 – 08/07
1079 â‚¬/nighttotal: 5395 â‚¬ (5 )

The Dazzling Two-bedroom Two-bath Suite In Boston

1 2
apartment , Boston
This two-bedroom suite is situated in Boston, 1.0 kilometre from South Station and 0.97 kilometres from Back Bay, offering convenient access to attractions such as the Boston Tea Party Ship & Museum and the Freedom Trail.
Boasting 111 square metres of floor area, this flat accommodates up to 13 guests with two bathrooms, a fully equipped kitchen, air conditioning, a fireplace, and on-site amenities including a swimming pool, fitness centre, and garden, with complimentary WiFi and lift access.
Boston Pad: 2br Suite With Pool And Gym - Massachusetts
10 1 review
Massachusetts
24/07 – 27/07
1374 â‚¬/nighttotal: 4122 â‚¬ (3 )

Boston Pad: 2br Suite With Pool And Gym

2 2
apartment , Boston
This luxurious two-bedroom apartment is situated in Boston's South End, close to Fenway Park and Quincy Market, offering easy access to attractions such as the New England Aquarium and Museum of Science.
The 111 square metre (1194 square feet) property features two bathrooms, sleeps five guests, and includes a fully equipped kitchen, swimming pool access, and a terrace.
Trendy Brighton 1br W/ W/d, Gym, Near T, Shops + Dining, By Blueground - Massachusetts
10 1 review
Massachusetts
01/09 – 28/02
145 â‚¬/nighttotal: 26100 â‚¬ (180 )

Trendy Brighton 1br W/ W/d, Gym, Near T, Shops + Dining, By Blueground

1 1
apartment , Boston
This one-bedroom flat is situated in Brighton, a neighbourhood in Boston, just 0.16km from St. Elizabeth's Medical Center and within 5km of both Harvard University and Boston University. The flat has received excellent user, location, and cleanliness ratings, making it a great choice for travellers seeking a comfortable and convenient stay.
The flat can accommodate up to two guests and features a fully equipped kitchen with a fridge, oven, microwave, and dishwasher. Guests can enjoy a range of amenities, including a fitness centre, a terrace or balcony, a garden, and parking.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts holiday rentals with parking

Beautifully Renovated Downtown Luxury Condo, A Block From The Rock! - Massachusetts
9.9 229 reviews
Massachusetts
19/08 – 21/08
391 â‚¬/nighttotal: 782 â‚¬ (2 )

Beautifully Renovated Downtown Luxury Condo, A Block From The Rock!

2 4
apartment , Plymouth
This apartment is located in Plymouth's Cultural District, just a 0.8km walk from both the 1749 Court House and Museum and Plymouth Rock. It has excellent ratings for location, cleanliness, and overall user experience.
The 102 square metre apartment has two bedrooms, one bathroom, and comfortably accommodates four guests. It comes equipped with a fully fitted kitchen, laundry facilities, air conditioning, a Jacuzzi, a spa, and parking, ensuring a comfortable and enjoyable stay.
Charming Retreat / Close To Beaches - Massachusetts
9.8 115 reviews
Massachusetts
16/07 – 18/07
284 â‚¬/nighttotal: 568 â‚¬ (2 )

Charming Retreat / Close To Beaches

1 3
apartment , Gloucester
This Gloucester apartment is located in a peaceful cul-de-sac, just 0.8 kilometres from Gloucester's beaches and a 50-minute drive from Boston.
The self-catering property sleeps four guests in two bedrooms, one bathroom, and offers a fully-fenced garden, two parking spaces, central heating, air conditioning, and a kitchen with dishwasher, microwave, fridge and freezer; laundry facilities are shared.
Near Beaches And Dtwn Falmouth Family Home With Deck - Massachusetts
8.7 48 reviews
Massachusetts
23/12 – 30/12
338 â‚¬/nighttotal: 2366 â‚¬ (7 )

Near Beaches And Dtwn Falmouth Family Home With Deck

3 6
house , Falmouth
This charming house is situated in East Falmouth, just 27 kilometres from the Sandwich Glass Museum and 29 kilometres from the John F Kennedy Hyannis Museum, offering a peaceful retreat close to attractions. It has received very good user ratings, an excellent location rating, and a good cleanliness rating.
The property is a spacious three-bedroom, three-bathroom home with a floor area of 139 square metres, comfortably accommodating up to eight guests. The house offers a range of amenities, including a fully equipped kitchen, air conditioning, a private garden, a spa, a tennis court, and parking, ensuring a comfortable and enjoyable stay.
Near Scenic Fresh Pond, Charles River, Shops,  Harvard Sq Access , Free Parking - Massachusetts
9.3 552 reviews
Massachusetts
10/11 – 07/01
119 â‚¬/nighttotal: 6902 â‚¬ (58 )

Near Scenic Fresh Pond, Charles River, Shops, Harvard Sq Access , Free Parking

1 2
apartment , Cambridge
This one-bedroom flat is located in West Cambridge, just over a mile from Harvard University and Harvard Square, offering a peaceful setting while being close to the city's attractions. The property has received excellent ratings for its location, cleanliness, and overall experience.
The 31 square metre flat features a comfortable living space with a fully equipped kitchen, a relaxing garden, and a spa tub. Guests can enjoy amenities such as free Wi-Fi, a patio, and parking.
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