Vacation 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

Lakeview Getaway With Hot Tub - Massachusetts
Massachusetts
26/06 – 28/06
A$962/nighttotal: A$1924 (2 )

Lakeview Getaway With Hot Tub

3 2
house , Billerica
This Billerica holiday home is situated an 8-minute walk from Micozzi Beach, 16 km from Minute Man National Historical Park, and 24 km from the Brattle Theatre.
The 130 square metre property boasts three bedrooms, two bathrooms, sleeps up to 15 guests, and includes a fully equipped kitchen, Jacuzzi, terrace, garden, free Wi-Fi, parking, and barbecue facilities; nearby attractions include a casino and fishing opportunities.
Artful Escape  Minutes To Salem, Beach And Train To Boston  Private Parking - Massachusetts
9.2 24 reviews
Massachusetts
01/08 – 06/08
A$549/nighttotal: A$2745 (5 )

Artful Escape Minutes To Salem, Beach And Train To Boston Private Parking

2 3
apartment , Beverly
This Beverly flat is conveniently located within a 1.6km walk of the Lacrom Theatre and John Cabot House, and under 5km from Northeast Hospital Corporation – Beverly Campus and Endicott College.
The 72 square metre self-catering property offers two bedrooms, one bathroom, sleeps four, and includes free Wi-Fi, on-site parking, and a fully equipped kitchen; babysitting is available on request.
5br Berkshire Home Mins To The Mountain & River - Massachusetts
9.6 9 reviews
Massachusetts
03/07 – 05/07
A$1054/nighttotal: A$2108 (2 )

5br Berkshire Home Mins To The Mountain & River

1 12
apartment , Charlemont
This newly renovated 5-bedroom house is located in Charlemont, under 5 kilometres from Berkshire East Resort, providing easy access to year-round outdoor activities.
This family-friendly property accommodates up to 12 guests with 5 bedrooms and a pull-out couch, featuring a fully equipped kitchen, air conditioning, a garden with a fire pit and gas BBQ, and a shuffleboard table, all within elegant 1920s-inspired décor.
Velocity Residence - Massachusetts
9.8 5 reviews
Massachusetts
21/06 – 23/06
A$462/nighttotal: A$924 (2 )

Velocity Residence

4 3
house , Worcester
Velocity Residence, a house in Worcester, is situated 3.5 kilometres from Worcester Polytechnic Institute and 3 kilometres from Worcester Regional Airport, with the DCU Center Arena & Convention Centre 4.5 kilometres away.
This family-friendly property offers 4 bedrooms, 2 bathrooms, a kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, and parking for up to 10 guests, featuring a private water park and complimentary WiFi.

Top cities

Best pet friendly Massachusetts holiday rentals

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

Lovely Lakeside Cottage - Massachusetts
9.8 184 reviews
Massachusetts
27/06 – 30/06
A$417/nighttotal: A$1251 (3 )

Lovely Lakeside Cottage

1 3
house , Dartmouth
This lakeside cottage is located in southeastern Massachusetts, just a short drive from Boston, Providence, Newport, and Cape Cod, with several beaches within 32km. The property has received excellent ratings for its cleanliness, location, and overall user experience.
This charming cottage offers a comfortable and welcoming space for two guests. Amenities include a fully equipped kitchen, a washer and dryer, air conditioning, and a private garden, making it perfect for a relaxing getaway.
39 - 3br Quincy - Stunning Townhouse Near Adams - Massachusetts
9.7 237 reviews
Massachusetts
16/07 – 23/07
A$737/nighttotal: A$5159 (7 )

39 - 3br Quincy - Stunning Townhouse Near Adams

3 7
apartment , Quincy
This newly built townhouse is located in Quincy, just 15 kilometres from Boston South Station and Back Bay, and 11 kilometres from the JFK Presidential Library & Museum. The apartment has received excellent ratings for location, cleanliness and user experience.
This three-bedroom apartment offers 177 square metres of space and can comfortably accommodate up to 13 guests. The apartment includes modern amenities such as a fully equipped kitchen with a dishwasher, air conditioning, free parking, and Wi-Fi.
The Milton Manor 3br 1ba - Sleeps 6 - Unit 1 - Fifa World Cup 2026 - Massachusetts
Massachusetts
26/06 – 03/08
A$487/nighttotal: A$18506 (38 )

The Milton Manor 3br 1ba - Sleeps 6 - Unit 1 - Fifa World Cup 2026

3 5
apartment , Milton
This newly renovated flat in Milton, located south of Boston, offers convenient access to Route 138, Blue Hills Parkway, I-95, and I-93, placing you just a 32-kilometre drive from downtown Boston and a short distance from the Blue Hills Reservation for outdoor recreation.
This family-friendly property spans 102 square metres, featuring three bedrooms to accommodate up to six guests, with amenities including high-speed Wi-Fi, a fully equipped kitchen, an in-unit washer/dryer, and off-street parking for up to four small cars.
Elegant Oasis With Pool And Gym - Massachusetts
10 9 reviews
Massachusetts
26/06 – 03/08
A$405/nighttotal: A$15390 (38 )

Elegant Oasis With Pool And Gym

2 5
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.

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. Plymouth, the site of the Pilgrims' landing, offers a glimpse into early American history. Salem's maritime history and association with the Salem Witch Trials are captivating. Beyond the cities, the charming towns of Nantucket and Martha's Vineyard offer beautiful beaches and quaint New England architecture.
  • What are the best Airbnb and holiday rentals in Massachusetts?

    Near Boston Historic Two-bedroom With Modern Amenities, Luxurious Renovated House and 2bed/2bath Apt At Waltham Landing - Middle Unit 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 massive canyons, its natural beauty is subtle yet striking. The coastline offers dramatic cliffs and sandy beaches. The Berkshires region provides stunning mountain scenery, perfect for hiking and scenic drives. The diverse ecosystems support a wide variety of plant and animal life. Specific locations include the dramatic cliffs of the North Shore and the rolling hills of the Pioneer Valley.
  • What are the most popular Airbnbs in Massachusetts?

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

    Pack for all types of weather, as Massachusetts experiences varied conditions throughout the year. Comfortable walking shoes are a must, especially for exploring Boston and other historic towns. Layers of clothing are recommended, as temperatures can fluctuate. Don't forget sunscreen, a hat, and sunglasses, particularly during the summer months. A reusable water bottle is also a good idea, to stay hydrated while exploring.
  • What are the best holiday rentals with a pool in Massachusetts?

    Captain Gosnold Village, The Cozy Carriage House - A+ Location - Luxking and Berkshire Mountain Lodge 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 athletic event. The Salem Haunted Happenings festival celebrates the city's spooky history. Numerous smaller town festivals and fairs take place throughout the summer and autumn, celebrating local produce and crafts. Specific dates vary annually, so checking local event listings closer to your travel dates is advisable.
  • What are the best rentals for families and kids in Massachusetts?

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

    Numerous restaurants across Massachusetts showcase local cuisine. In Boston, look for places specialising in New England clam chowder, lobster rolls, and Boston baked beans. Many restaurants in coastal towns offer fresh seafood. The Berkshires region features farm-to-table restaurants using locally sourced ingredients. Specific restaurant recommendations would require more detail on your preferred location and cuisine.
  • What are the best rentals or Airbnbs with a jacuzzi in Massachusetts?

  • What are some less-famous attractions in Massachusetts that are worth a visit?

    Beyond the well-known sites, explore the charming towns of the Berkshires, such as Lenox and Stockbridge, offering beautiful scenery and cultural attractions. The Plimoth Patuxet Museums provide a more immersive experience of early colonial life than just Plymouth Rock. The Cape Cod National Seashore offers stunning beaches and hiking trails away from the more crowded areas.
  • What are the best activities for engaging with locals and understanding their culture in Massachusetts?

    Visiting local farmers' markets provides a great opportunity to interact with residents and sample regional produce. Attending smaller town festivals and fairs offers a chance to experience local traditions and customs. Exploring neighbourhoods beyond the main tourist areas, such as the North End in Boston or the Back Bay, allows for a more authentic experience of daily life.
  • What unique natural landscapes and terrain features can travellers explore in Massachusetts?

    Massachusetts offers diverse landscapes. The coastline features dramatic cliffs, sandy beaches, and salt marshes. Inland, the terrain varies from rolling hills and farmland to the mountainous regions of the Berkshires. The state's many forests and parks provide opportunities for hiking, biking, and wildlife viewing. Specific areas include the Cape Cod National Seashore, the Berkshires, and the Quabbin Reservoir.
  • How many days are ideal for a trip to Massachusetts, and what are some itinerary suggestions?

    The ideal length of a trip depends on your interests. A long weekend (3-4 days) could focus on Boston and its surrounding areas. A week-long trip could incorporate Boston, a coastal town like Salem or Plymouth, and a day trip to a location like the Berkshires. Two weeks would allow for a more in-depth exploration of the state's diverse regions.

Nearby regions

Best Massachusetts holiday rentals with a pool

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

The Mansion At Ocean Edge Resort & Golf Club - Massachusetts
8.3 2671 reviews
Massachusetts
26/06 – 03/08
A$1905/nighttotal: A$72390 (38 )

The Mansion At Ocean Edge Resort & Golf Club

2 5
resort , Brewster
The Mansion at Ocean Edge Resort and Golf Club is located in Brewster, a short drive from the Cape Cod Museum of Natural History and the Wellfleet Drive-In Theater & Cinemas. It has consistently received very good ratings for location, cleanliness, and overall user experience.
The resort offers a range of accommodation options, including guest rooms with patios or balconies and villas with full kitchens and living rooms. Guests can enjoy a private beach, two swimming pools, a spa, a fitness centre, tennis courts, and a variety of dining options, including a pub, a tavern, and a seasonal terrace.
Spacious Vacation Townhome Unit With A Pool - Massachusetts
9.8 18 reviews
Massachusetts
31/08 – 07/09
A$564/nighttotal: A$3948 (7 )

Spacious Vacation Townhome Unit With A Pool

3 2
apartment , Weston
This Weston holiday home is situated in a peaceful rural setting, approximately 4 km from Brandeis University and under 10 km from Boston Children's Hospital in Waltham.
The 186 square metre property boasts three bedrooms sleeping six, two bathrooms, a private outdoor pool and spa, a fully equipped kitchen, and free Wi-Fi; barbecue facilities are also available for al fresco dining.
A Timeless Retreat At Historic Crompton House - Massachusetts
Massachusetts
12/07 – 17/07
A$637/nighttotal: A$3185 (5 )

A Timeless Retreat At Historic Crompton House

2 4
house , Worcester
This holiday home is situated in Worcester, a short walk from Worcester Polytechnic Institute and the DCU Centre Arena & Convention Centre, and 1.8 kilometres from Worcester, MA Station.
This property offers 158 square metres of living space for up to 7 guests, featuring 2 bedrooms, 2 bathrooms, air conditioning, an outdoor swimming pool, a hot tub, and a well-equipped kitchen.
Gateway To Cape Cod Vacation Cottage 1 - Massachusetts
8.8 38 reviews
Massachusetts
14/09 – 16/09
A$259/nighttotal: A$518 (2 )

Gateway To Cape Cod Vacation Cottage 1

1 2
resort , Rochester
Gateway To Cape Cod Vacation Cottage 1 is situated in Rochester, just a short drive from popular attractions like Plimoth Plantation, Heritage Museums & Gardens, and Sandwich Glass Museum, making it an ideal base for exploring the area. The cottage has received consistently high ratings for its location, cleanliness, and overall experience.
Each cottage features a private patio and a fully equipped kitchen, allowing guests to enjoy a comfortable and independent stay. Guests can also enjoy amenities such as a swimming pool, garden, restaurant, fitness centre, and parking, ensuring a relaxing and enjoyable holiday.

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
A$240/nighttotal: A$14400 (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.
Enjoyable 2-bedroom Lower Level Apartment In Charming Lynn - Massachusetts
9.4 6 reviews
Massachusetts
18/07 – 19/07
A$384/nightfor 1 night

Enjoyable 2-bedroom Lower Level Apartment In Charming Lynn

2 2
apartment , Lynn
This two-bedroom flat in Lynn offers convenient access to Boston's attractions, situated an 18-minute drive from Boston Common and a 9-minute drive from Revere Beach, with Lynn Station just a 7-minute walk away for easy public transport.
This serviced apartment accommodates up to five guests and includes on-site parking, free Wi-Fi, and air conditioning, providing a comfortable base for exploring nearby entertainment venues like Encore Boston Harbor and TD Garden.
Historic Home With Modern Updates On Less Than 4 Acres - Massachusetts
9.9 85 reviews
Massachusetts
03/07 – 15/07
A$491/nighttotal: A$5892 (12 )

Historic Home With Modern Updates On Less Than 4 Acres

4 4
house , Royalston
This Royalston house, a spacious property situated 48km from Amherst College and 37km from the Pelham Town Hall Historic District, offers easy access to local attractions.
The 297 square metre dwelling boasts four bedrooms, sleeping eight guests, and includes a fully equipped kitchen with dishwasher, washing machine, air conditioning, free Wi-Fi, and a garden with parking.
Apartments In Salem - Massachusetts
9.0 816 reviews
Massachusetts
12/07 – 17/07
A$612/nighttotal: A$3060 (5 )

Apartments In Salem

3 4
apartment , Salem
This three-bedroom apartment is situated on the North Shore of Salem, just a short distance from the historic district and the Salem waterfront, offering a peaceful setting close to the bustling attractions. The apartment has received very good ratings for its location, cleanliness, and overall experience.
The apartment provides a comfortable space for families or groups of up to six people. It features a fully equipped kitchen, a terrace or balcony, and a garden, making it ideal for enjoying meals and relaxing outdoors. Guests also have access to free WiFi, air conditioning, and parking.
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