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

Spacious 5br Executive Retreat - 10 Min To Boston - Massachusetts
10 8 reviews
Massachusetts
03/07 – 05/07
832 €/nighttotal: 1664 € (2 )

Spacious 5br Executive Retreat - 10 Min To Boston

1 12
apartment , Milton
This East Milton flat offers a peaceful retreat, situated just 1.6 kilometres from Downtown Boston and Wollaston Beach.
This spacious property accommodates up to 12 guests, boasting a chef's kitchen, three office spaces, a spa-like bathroom with a rain shower, and private parking for three vehicles, with convenient access to Logan Airport (24 kilometres) and Blue Hills Reservation (19 kilometres).
Updated Apt W/ Shared Yard: Near Events & Boston - Massachusetts
9.8 10 reviews
Massachusetts
19/07 – 24/07
180 €/nighttotal: 900 € (5 )

Updated Apt W/ Shared Yard: Near Events & Boston

1 4
apartment , Stoughton
This family-friendly Stoughton apartment, a 3-minute walk from Stoughton station, is conveniently located near the Stoughton Book Shop and New England Sinai Hospital (within 3.2km), and Blue Hills Reservation and Memorial Park Beach (within 9.7km).
The 111 square metre dwelling boasts one bedroom, one bathroom, sleeps four, and includes a fully equipped kitchen, fireplace, washing machine, free Wi-Fi, parking, and access to family-friendly amenities such as games and a foosball table.
Riverview Charming Apt Near Beach - Massachusetts
9.8 34 reviews
Massachusetts
19/08 – 21/08
220 €/nighttotal: 440 € (2 )

Riverview Charming Apt Near Beach

2 4
apartment , Ipswich
This Ipswich apartment is conveniently located near the Ipswich River and Ipswich Museum, within a 10-minute walk, and a short distance (4.8km) from the Parker River National Wildlife Refuge and Ipswich railway station.
This two-bedroom, one-bathroom flat sleeps six, offering a fully equipped kitchen with dishwasher, free Wi-Fi, on-site parking, and air conditioning; nearby attractions include birdwatching at the Parker River National Wildlife Refuge and exploring Ipswich's history at the museum.
3br Immaculate And Sunny Home Near The Beach! - Massachusetts
9.8 106 reviews
Massachusetts
31/07 – 07/08
264 €/nighttotal: 1848 € (7 )

3br Immaculate And Sunny Home Near The Beach!

1 1
apartment , Hull
This charming upper duplex is located just 7 houses from Nantasket Beach, a short walk from a quaint shopping area and a 30-minute ferry ride from Boston. The property enjoys excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This cosy apartment offers three bedrooms and one bathroom, comfortably accommodating up to four guests. A fully equipped kitchen, a spacious living area, an outdoor shower, beach supplies, and a garden with parking are all included, offering everything needed for a relaxing beach getaway.

Top cities

Best pet friendly Massachusetts holiday rentals

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

Private Studio W/ Loft Center Historic Carlisle - Massachusetts
9.4 33 reviews
Massachusetts
24/07 – 26/07
165 €/nighttotal: 330 € (2 )

Private Studio W/ Loft Center Historic Carlisle

1 2
studio , Carlisle
This holiday home is located in Carlisle, just 1.5 km from Great Brook Farm State Park and 4.2 km from Concord River, offering easy access to outdoor activities and scenic beauty. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The accommodation features one bedroom and one bathroom, comfortably accommodating up to four guests. The property provides free Wi-Fi, a fully equipped kitchen, a TV, and a selection of books, ensuring a comfortable and enjoyable stay.
558-3 3br Boston - Modern Nest Near Franklin Park - Massachusetts
9.8 5 reviews
Massachusetts
03/07 – 05/07
998 €/nighttotal: 1996 € (2 )

558-3 3br Boston - Modern Nest Near Franklin Park

3 12
apartment , Boston
This three-bedroom Boston apartment, situated near the New England Aquarium, is conveniently located approximately 8 kilometres from Fenway Park and South Station.
The 75-square-metre self-catering flat boasts two bathrooms, free Wi-Fi, private parking, and sleeps up to 25 guests, making it ideal for families or large groups visiting the city.
Warm 1br In Boston Fidi Close To Everything - Massachusetts
8.5 2 reviews
Massachusetts
27/06 – 04/07
332 €/nighttotal: 2324 € (7 )

Warm 1br In Boston Fidi Close To Everything

1 2
apartment , Boston
This Boston Financial District flat is situated less than 1km from King's Chapel and Burying Ground, and within 1.6km of the Freedom Trail.
The 50 square metre one-bedroom apartment sleeps three, features a fully equipped kitchen, washing machine, air conditioning, and free Wi-Fi.
Newly Renovated 4br Boston Apt W/ Kid Friendly - Exclusive Fifa 2026 Deal 90/2 - Massachusetts
10 1 review
Massachusetts
05/07 – 10/07
1029 €/nighttotal: 5145 € (5 )

Newly Renovated 4br Boston Apt W/ Kid Friendly - Exclusive Fifa 2026 Deal 90/2

4 14
apartment , Boston
This Dorchester apartment is situated a 6-minute drive from the JFK Presidential Library and Museum and a 5-minute drive from Franklin Park Zoo, with Fields Corner underground station a 12-minute walk away for city exploration.
This spacious 4-bedroom, 2-bathroom flat accommodates up to 15 guests and offers amenities including air conditioning, free Wi-Fi, a fully equipped kitchen, and on-site parking, with laundry facilities and linens provided for your convenience.

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

Stylish And Cozy At Revere Beach - Massachusetts
Massachusetts
10/11 – 08/12
254 €/nighttotal: 7112 € (28 )

Stylish And Cozy At Revere Beach

1 2
apartment , Revere
This Revere apartment, a short 1.4km stroll from Revere Beach and 8.8km from Boston's historic district, offers easy access to both the coast and the city's attractions.
The 450 square metre flat boasts one bedroom, one bathroom, sleeps five, and includes a fully equipped kitchen, in-unit laundry, free Wi-Fi, air conditioning, a swimming pool, and a fireplace.
What A Gem City Views And A Rooftop Pool Await - Massachusetts
Massachusetts
03/07 – 04/07
1115 €/nightfor 1 night

What A Gem City Views And A Rooftop Pool Await

1 4
apartment , Boston
This Boston flat offers a prime location, a 14-minute walk to the Freedom Trail and 0.9 miles (approximately 1.45 kilometres) from Boston Common, placing you close to the Old State House and King's Chapel and Burying Ground.
This 70 square metre residence accommodates up to 9 guests, featuring air conditioning, a fully equipped kitchen with a dishwasher and oven, free Wi-Fi, a fitness centre, a rooftop pool with city views, and access to an on-site casino and water park.
Sleeps 15 • Pool • World Cup 2026 • Retreat - Massachusetts
9.8 80 reviews
Massachusetts
05/07 – 10/07
1381 €/nighttotal: 6905 € (5 )

Sleeps 15 • Pool • World Cup 2026 • Retreat

4 14
apartment , Brimfield
This spacious Brimfield house, a five-minute drive from Interstates 90 and 84 (approximately 8km), offers panoramic hilltop views and is 72km from Hartford and 160km from Boston.
The four-bedroom, two-bathroom property sleeps up to 16 guests, boasting a large open-plan layout with a 12-person farm table, fireplace, well-equipped kitchen, swimming pool, and garden; optional hospitality services are available.
World Cup, Walk To Train And Free Parking - Massachusetts
Massachusetts
28/06 – 29/06
535 €/nightfor 1 night

World Cup, Walk To Train And Free Parking

1 2
apartment , Norwood
This family-friendly flat in Norwood is situated 20.9 kilometres from the Museum of Fine Arts and Fenway Park, and 1.9 kilometres from Norwood Memorial Airport, offering convenient access to Boston's attractions and transport links.
This spacious 102 square metre apartment sleeps up to seven guests and features air conditioning, a fully equipped kitchen with a fridge, microwave and dishwasher, a private swimming pool, and free on-site parking, with easy access to the train for commuting.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts holiday rentals with parking

The Retro Apartment In Revere With Outdoor Area - Massachusetts
8.8 5 reviews
Massachusetts
01/08 – 30/09
146 €/nighttotal: 8760 € (60 )

The Retro Apartment In Revere With Outdoor Area

1 2
apartment , Revere
This Revere apartment is conveniently located near Revere Beach (13km), Encore Boston Harbor (14km), and Boston Common (21km), offering easy access to major attractions.
The one-bedroom, one-bathroom flat sleeps two guests and includes Wi-Fi, air conditioning, a dryer, towels, toiletries, and is ideal for exploring Revere and Boston.
Modern Apartment Cambridge Near Harvard Mit - Massachusetts
9.0 1 review
Massachusetts
27/06 – 04/07
699 €/nighttotal: 4893 € (7 )

Modern Apartment Cambridge Near Harvard Mit

2 2
apartment , Cambridge
This residence is located 5.95 kilometres from Logan Airport, providing convenient travel links for visitors to Cambridge.
This 130 square metre flat offers two bedrooms, two bathrooms and accommodates up to 11 guests, featuring a kitchen, air conditioning, a terrace, garden, fitness centre, tennis court, and on-site parking.
167 M² House ∙ 2 Bedrooms ∙ 4 Guests - Massachusetts
Massachusetts
01/08 – 30/09
200 €/nighttotal: 12000 € (60 )

167 M² House ∙ 2 Bedrooms ∙ 4 Guests

2 2
house , Quincy
House to rent for 4 guests. You will be located in Quincy.
Facilities and services include a kitchen, air conditioning and a freeze. Take advantage of the garden in this house in Quincy.
Luxurious 2br - 2ba Apt At Hyatus - Massachusetts
9.6 22 reviews
Massachusetts
01/07 – 31/07
416 €/nighttotal: 12480 € (30 )

Luxurious 2br - 2ba Apt At Hyatus

3 2
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.
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