Villas and Holiday homes in Massachusetts

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Massachusetts holiday homes
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10727 Villa rentals in Massachusetts

Best Massachusetts villas and holiday homes with a pool

Among the 10727 accommodations in Massachusetts, here are the 4 best villas and holiday homes with a pool

Lavish Boston Mansion For Short And Mid Term Stays - Massachusetts
Massachusetts
10/11 – 07/01
1602 €/nighttotal: 92916 € (58 )

Lavish Boston Mansion For Short And Mid Term Stays

8 2
house , Dedham
This Dedham Luxe Grand Colonial property, situated approximately 16-19 kilometres from Boston attractions including the Museum of Fine Arts, Fenway Park, Boston University, and the Hynes Convention Centre, offers a luxurious stay.
This five-bathroom, one-bedroom residence boasts a 763 square metre floor area, accommodating up to 16 guests and featuring a private pool, free parking, and a fully equipped kitchen; washer/dryer and Wi-Fi are also included.
Shared Hot Tub Historic Cottage, Walk To Elm Park - Massachusetts
9.0 5 reviews
Massachusetts
07/01 – 12/01
302 €/nighttotal: 1510 € (5 )

Shared Hot Tub Historic Cottage, Walk To Elm Park

2 2
house , Worcester
This historic cottage is situated in Worcester, just a short walk from Elm Park, 0.96 kilometres from Worcester Polytechnic Institute, and 24 kilometres from the DCU Center Arena & Convention Center. The cottage offers a peaceful setting close to the city centre, allowing easy access to Worcester's attractions.
The 2-bedroom cottage has a floor area of 111 square metres and can accommodate up to 7 guests. The house features a fully equipped kitchen, a garden, a swimming pool, and parking, making it an ideal choice for families or groups of friends.
Private Heated Pool: Family Cottage In Plymouth! - Massachusetts
10 3 reviews
Massachusetts
07/01 – 12/01
267 €/nighttotal: 1335 € (5 )

Private Heated Pool: Family Cottage In Plymouth!

2 2
cottage , Plymouth
This Plymouth holiday home is situated less than 1.6km from Plymouth Long Beach and a short drive from Plimoth Patuxet Museums, offering easy access to the coast and local historical attractions.
The 91 square metre property sleeps six guests across two bedrooms and one bathroom, boasting a private heated pool, fenced garden, Smart TVs, and a well-equipped kitchen including a dishwasher.
Sunset Waterfront Retreat | Private Beach, Pool & Firepit - Massachusetts
9.8 131 reviews
Massachusetts
10/11 – 07/01
385 €/nighttotal: 22330 € (58 )

Sunset Waterfront Retreat | Private Beach, Pool & Firepit

2 2
cottage , Newburyport
This charming waterfront cottage is situated just a short distance from the bustling centre of Newburyport, offering a tranquil escape with stunning views of the marsh. It has received excellent ratings for location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay.
The property features three bedrooms, accommodating up to six guests, and a modern kitchen equipped with a dishwasher, washer, and dryer. Guests can enjoy the private pool, relax on the beach, explore the island on bikes provided, and witness breathtaking sunsets over the water.

Top cities

Best family friendly Massachusetts villas and holiday home

Among the 10727 accommodations in Massachusetts, here are the 4 best family friendly villas and holiday homes

Cottage With Direct Water Access! - Massachusetts
10 119 reviews
Massachusetts
10/11 – 07/01
350 €/nighttotal: 20300 € (58 )

Cottage With Direct Water Access!

2 2
cottage , Ipswich
This family-friendly cottage is situated on the waterfront in Ipswich, just under 2 kilometres from the Parker River National Wildlife Refuge and Ipswich River, and within 5 kilometres of Clark Beach and the Ipswich Museum. The cottage is rated excellent by previous guests, ensuring a comfortable and enjoyable stay.
The 77 square metre cottage features two bedrooms and one bathroom, comfortably accommodating up to four guests. Enjoy modern amenities like free WiFi, a DVD player, and a fully equipped kitchen, as well as outdoor spaces like a terrace, garden, and a spa.
Sakura House: Spacious 4br W/ Gym & Premium Design - Massachusetts
9.5 42 reviews
Massachusetts
16/07 – 23/07
567 €/nighttotal: 3969 € (7 )

Sakura House: Spacious 4br W/ Gym & Premium Design

1 7
house , Northborough
This four-bedroom, three-bathroom house is situated in Northborough, just a short distance from the Apex Centre and major highways, making it ideal for exploring the surrounding area.
The property boasts a spacious living area, a fully equipped kitchen with modern appliances, a dedicated office space, a private in-law apartment, and a bonus room with a gym and play area, comfortably accommodating up to 10 guests.
Magical Little Home In Historic District I Parking I Rustic Luxury I Outdoor Seating - Massachusetts
9.9 28 reviews
Massachusetts
07/01 – 12/01
225 €/nighttotal: 1125 € (5 )

Magical Little Home In Historic District I Parking I Rustic Luxury I Outdoor Seating

1 2
house , Marblehead
This detached house is situated in Marblehead's historic district, a 19-minute walk from Gas House Beach and approximately 6.4 kilometres from the Peabody Essex Museum.
This property offers 118 square meters of living space, accommodating up to three guests with one bedroom and two bathrooms, and features a fully equipped kitchen, air conditioning, and complimentary Wi-Fi.
Shore House Steps To The Ocean, 18 Min Ferry To Boston - Massachusetts
8.8 2 reviews
Massachusetts
10/11 – 07/01
480 €/nighttotal: 27840 € (58 )

Shore House Steps To The Ocean, 18 Min Ferry To Boston

4 2
cottage , Hull
This Hull seaside property, situated 3.2km from Nantasket Beach and within 32km of South Shore Hospital and South Shore Plaza, offers stunning ocean views.
This four-bedroom, two-bathroom holiday home boasts 130 square metres of space, sleeps eight guests, and includes a fully equipped kitchen, private patio, garden, parking, and free Wi-Fi.

Frequently asked questions about villa rentals in Massachusetts

  • What are the must-see attractions in Massachusetts?

    Massachusetts boasts a wealth of attractions. For history buffs, a trip to Boston is essential, with sites like the Freedom Trail, Faneuil Hall, and the Boston Tea Party Ships & Museum. Outside of Boston, Plymouth offers a glimpse into the Pilgrims' history at Plimoth Patuxet Museums. Art lovers should visit the Museum of Fine Arts in Boston or the Norman Rockwell Museum in Stockbridge. And for natural beauty, the Berkshires offer stunning mountain scenery and charming towns.
  • What are the best villa rentals in Massachusetts?

    Among the villa rentals in Massachusetts, Luxurious Harbor View Cindy Cottage - Walk & Bike To Everything, Luxurious Renovated House and Captain Gosnold Village are the most popular ones.

  • Is Massachusetts known for mountains, beaches, forests, or other types of landscapes?

    Massachusetts offers a diverse range of landscapes. The Berkshires region in western Massachusetts features rolling hills and mountains, perfect for hiking and outdoor activities. The coastline provides beautiful beaches, particularly on Cape Cod and the islands of Nantucket and Martha's Vineyard. Extensive forests are found throughout the state, offering opportunities for hiking and exploring. In addition to these, you'll also find charming coastal towns and vibrant cityscapes.
  • What are the best villa rentals with a pool in Massachusetts?

  • What are some surprising and hidden attractions in Massachusetts?

    Beyond the well-known spots, Massachusetts holds many surprises. The Mount Auburn Cemetery in Cambridge, while a cemetery, is a beautifully landscaped Victorian-era space with stunning architecture and historical significance. The Fruitlands Museum in Harvard offers a unique blend of history, art, and nature. And for a quirky experience, explore the quirky roadside attractions along Route 6A on Cape Cod.
  • What are the best villa rentals with a jacuzzi in Massachusetts?

  • What are some unique ways to learn about the culture of Massachusetts by engaging with its people?

    To truly understand Massachusetts culture, consider attending a local town meeting – a quintessential New England experience. Visiting a local farm and participating in a harvest festival provides a connection to the agricultural heritage. Exploring the many farmers' markets across the state offers opportunities to interact with local producers and sample regional products. Finally, attending a performance at the Tanglewood Music Center in Lenox provides a cultural immersion in the arts.
  • What are the best villa rentals for families and kids in Massachusetts?

  • How much time should you set aside to thoroughly explore Massachusetts?

    A week allows for a good overview of Massachusetts, hitting major cities and attractions. However, to truly experience the state's diversity – from Boston to the Berkshires and Cape Cod – two weeks or even more would be ideal. It depends on your interests and preferred pace of travel.
  • What are the best pet friendly villa rentals in Massachusetts?

  • Is there anything you might not think to pack for Massachusetts?

    Depending on the time of year, you might overlook packing layers. Massachusetts weather can be unpredictable, even in summer. Comfortable walking shoes are a must, as exploring many towns and historical sites involves a lot of walking. Finally, insect repellent can be useful, especially during warmer months.
  • What are the best villa rentals with parking in Massachusetts?

  • What cultural experiences or workshops in Massachusetts offer something different?

    The Massachusetts Institute of Technology (MIT) offers public lectures and events, providing access to cutting-edge science and technology. Many historical societies and museums offer workshops on topics ranging from historical crafts to local art forms. Check local listings for specific offerings, as these vary seasonally.
  • Are there any food festivals in Massachusetts where you can try local food?

    The Boston Seafood Festival is a popular annual event showcasing fresh seafood. Many smaller towns and regions host their own agricultural fairs and festivals throughout the year, offering opportunities to sample local produce, baked goods, and other regional specialties. Check local event listings for specific dates and locations.
  • What seasonal natural events, such as migrations or blooming periods, occur in Massachusetts?

    Spring brings the blooming of wildflowers across the state, particularly in the Berkshires. Autumn showcases vibrant foliage, with peak colour typically occurring in October. Bird migration is a significant event, with various species passing through during spring and autumn.
  • What exclusive experiences are available when visiting Massachusetts?

    A private tour of the Isabella Stewart Gardner Museum in Boston, focusing on its unique history and collection, offers an exclusive experience. A private whale watching tour from Cape Cod provides a more intimate experience of observing these magnificent creatures. Similarly, a private guided hike in the Berkshires, tailored to your interests, can offer a unique perspective on the region's natural beauty.

Nearby regions

Best Massachusetts villas and holiday homes with a kitchen

5 Mi To Td Garden Quiet Medford Getaway! - Massachusetts
8.0 2 reviews
Massachusetts
18/07 – 24/07
319 €/nighttotal: 1914 € (6 )

5 Mi To Td Garden Quiet Medford Getaway!

2 4
house , Medford
This Medford house, a peaceful retreat 8km from Boston's TD Garden and within a 6-8km radius of Harvard Square, Inman Square, and the Brattle Theatre, offers easy access to major attractions.
The 121 square metre property boasts two bedrooms, two bathrooms, sleeps nine guests, and includes a fully equipped kitchen with fridge, microwave, and dishwasher, plus free Wi-Fi and parking.
Rustic-chic Cottage With Yard And Grill - Near Hiking! - Massachusetts
9.7 35 reviews
Massachusetts
26/06 – 28/06
192 €/nighttotal: 384 € (2 )

Rustic-chic Cottage With Yard And Grill - Near Hiking!

2 2
house , Northfield
The Rustic-Chic Cottage is located in Northfield, just 39 kilometres from both Amherst College and the Beneski Museum of Natural History, making it a great base for exploring the area. The cottage has received excellent ratings for user experience, location, and cleanliness.
This 2-bedroom cottage sleeps 2 guests and offers 125 square metres of living space. The cottage is fully equipped with a kitchen, air conditioning, free Wi-Fi, a garden, and free bikes, plus it has a patio with river views and is close to hiking trails.
A Timeless Retreat At Historic Crompton House - Massachusetts
Massachusetts
12/07 – 08/08
254 €/nighttotal: 6858 € (27 )

A Timeless Retreat At Historic Crompton House

2 4
house , Worcester
This historic Crompton House is situated in a convenient Worcester district, offering direct access to Mechanics Hall and Hanover Theatre, and is under an hour by train to Boston.
This 2-bedroom, 2-bathroom dwelling accommodates up to 4 guests and features a private garden, shared swimming pool and hot tub, wood-burning fireplaces, on-site parking, and an espresso machine, with easy access to Worcester Public Market and Polar Park.
Ledge On Green - Massachusetts
Massachusetts
21/06 – 23/06
341 €/nighttotal: 682 € (2 )

Ledge On Green

1 3
house , Rockport
This Rockport residence, Ledge on Green, is located 2.1 kilometres from Back Beach and 35.4 kilometres from the Peabody Essex Museum.
This 123 square metre house offers accommodation for up to 7 guests, featuring 2 bedrooms, 2 bathrooms, a well-equipped kitchen with a dishwasher and microwave, a terrace with sea views, and on-site amenities including a children's playground and outdoor furniture.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts villas and holiday homes with jacuzzi

Fisherman's Paradise - Massachusetts
Massachusetts
04/10 – 31/10
645 €/nighttotal: 17415 € (27 )

Fisherman's Paradise

3 2
house , Newbury
Fisherman's Paradise, a beachfront property in Newburyport, Massachusetts, offers direct access to Newbury Beach and is a 31km drive from the Peabody Essex Museum and The House of the Seven Gables.
This 167 square metre holiday home boasts three bedrooms, two bathrooms including a jacuzzi, a fully equipped kitchen with dishwasher, parking, a private balcony with sea views, and accommodates up to 15 guests, with free Wifi and a garden.
Chilmark Luxury Quansoo Beach Access-4br - Massachusetts
Massachusetts
10/11 – 07/01
2954 €/nighttotal: 171332 € (58 )

Chilmark Luxury Quansoo Beach Access-4br

4 2
house , Chilmark
This beachfront property in Chilmark offers direct access to Quansoo Beach and is situated 7.1 kilometres from Martha's Vineyard Airport and 17.7 kilometres from Edgartown Lighthouse.
This spacious holiday home, covering 186 square metres, accommodates up to 15 guests with four bedrooms and four bathrooms, featuring air conditioning, a swimming pool, Jacuzzi, fitness centre, and a fully equipped kitchen, alongside complimentary Wi-Fi and private parking.
Elegant 3br Home In Worcester - Massachusetts
8.7 3 reviews
Massachusetts
10/11 – 07/01
246 €/nighttotal: 14268 € (58 )

Elegant 3br Home In Worcester

1 2
house , Worcester
This elegant three-bedroom house in Worcester is situated 6.1km from the DCU Center and 3.5km from Fitton Field, offering convenient access to local attractions.
The 167 square metre property boasts three bathrooms, sleeps nine guests, and includes a fully equipped kitchen, jacuzzi, garden, parking, and free Wi-Fi.
Tiffany's Treasure - Massachusetts
Massachusetts
27/06 – 30/06
1234 €/nighttotal: 3702 € (3 )

Tiffany's Treasure

4 3
house , Oak Bluffs
This spacious Oak Bluffs holiday home is situated 4km from Martha's Vineyard Airport and 10.6km from Edgartown Lighthouse, offering convenient access to local attractions.
The 176 square metre property boasts four bedrooms, three bathrooms including a jacuzzi, a fully equipped kitchen, and can comfortably accommodate up to fifteen guests, with a terrace, garden and free Wi-Fi.
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