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

Spacious Poolside Boston Stay Sleeps 8 Pet Friendly - Massachusetts
No reviews

Spacious Poolside Boston Stay Sleeps 8 Pet Friendly

house, Framingham
This Framingham house, situated approximately 24-29 kilometres from Boston attractions including Minute Man National Historical Park, Harvard Square, and Central Square, offers a convenient base for exploring the area.
The 140-square-metre property sleeps eight guests in four bedrooms and two bathrooms, boasting a swimming pool, garden, and fully equipped kitchen with a dishwasher; on-site amenities include billiards and table tennis.
The Clearing - Quiet - Close To Nature - Massachusetts
10 222 reviews

The Clearing - Quiet - Close To Nature

cottage, Chesterfield
This Chesterfield cottage, situated 0.3km from the Westfield River and 4.8km from the Chesterfield Gorge Reservation, offers easy access to hiking trails and scenic walks.
This 65 square metre self-catering holiday home sleeps four, boasting two bedrooms, one bathroom, a private pool, barbecue, fireplace, and free Wi-Fi.
Private Heated Pool: Family Cottage In Plymouth! - Massachusetts
9.0 6 reviews

Private Heated Pool: Family Cottage In Plymouth!

house, Plymouth
This Plymouth family cottage is situated a 1.6km walk from Plymouth Long Beach and less than 1km from Plimoth Patuxet Museums.
The 91 square metre property offers one bedroom, one bathroom, sleeps eleven guests, and boasts a private heated pool, free Wi-Fi, and a fully equipped kitchen including a dishwasher.
Relax & Renew At Luxury Villa With Heated Pool & Hot Tub,tennis,bikes,firepit! - Massachusetts
9.3 29 reviews

Relax & Renew At Luxury Villa With Heated Pool & Hot Tub,tennis,bikes,firepit!

apartment, Oak Bluffs
This family-friendly holiday home is located in Oak Bluffs, just a short distance from the beach, Circuit Avenue, and other local attractions. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The spacious 4-bedroom property spans 223 square metres and features a range of amenities including a private pool, a Jacuzzi, a tennis court, and a barbecue grill. Guests can enjoy the beautiful weather in the private garden or relax in the comfortable living spaces.

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 On Beautiful Long Pond  With Fantastic Sandy Lakefront Beach - Massachusetts
9.6 52 reviews

Cottage On Beautiful Long Pond With Fantastic Sandy Lakefront Beach

cottage, Plymouth
This Plymouth cottage is situated directly on the beach, just six miles from Pinehills Golf Club, Manomet Beach, and Waverly Oaks Golf Club. The property has consistently received excellent reviews for its location, cleanliness, and overall experience.
This two-bedroom holiday home, spanning 85 square metres, comfortably accommodates up to six guests. It offers a fully equipped kitchen, a private patio, a swimming pool, a jacuzzi, and a garden, making it ideal for families and groups seeking a relaxing and enjoyable stay.
House ∙ 2 Bedrooms ∙ 4 Guests - Massachusetts
No reviews

House ∙ 2 Bedrooms ∙ 4 Guests

house, Braintree Town
This Braintree residence is located in the Blue Hills area, offering straightforward access to Boston, approximately 16 kilometres away, and is also conveniently situated for exploring Quincy and various South Shore destinations.
This family-friendly house accommodates up to four guests in two bedrooms and features a fully equipped kitchen with a fridge, microwave, and dishwasher, alongside air conditioning and Wi-Fi, with driveway parking for two vehicles.
166 M² House ∙ 3 Bedrooms ∙ 5 Guests - Massachusetts
No reviews

166 M² House ∙ 3 Bedrooms ∙ 5 Guests

house, Somerville
House for 5 guests. This accommodation is located in Somerville.
Facilities and services include a kitchen, air conditioning and an iron. This is a family-friendly house!
Beachfront Stay Near Downtown Scituate - Massachusetts
No reviews

Beachfront Stay Near Downtown Scituate

house, Scituate
This beachfront holiday let in Scituate offers direct access to Sand Hills Beach and is located approximately 37 kilometres from the JFK Presidential Library & Museum.
This family-friendly accommodation includes free private parking, WiFi, a shared kitchen, a private balcony with barbecue, and both indoor and outdoor play areas, alongside a private beach area.

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

Fifa 40 Minutes To Gillette Steps From The Beach, Charming Cottage Plymouth Ma - Massachusetts
10 12 reviews

Fifa 40 Minutes To Gillette Steps From The Beach, Charming Cottage Plymouth Ma

cottage, Plymouth
This charming cottage is situated just a short distance from a private beach and pond, offering a peaceful retreat within easy reach of Plymouth's historic centre, just 5 km away. The cottage is highly rated by previous guests, receiving excellent reviews for its comfortable accommodation and convenient location.
The cottage has three bedrooms and one bathroom, comfortably accommodating up to eight guests. The property offers a range of amenities including a fully equipped kitchen, air conditioning, a garden, and parking, making it ideal for families and groups looking for a relaxing and enjoyable stay.
16 Mi To Boston: Home W/ Deck In Weymouth - Massachusetts
8.7 3 reviews

16 Mi To Boston: Home W/ Deck In Weymouth

house, Weymouth Town
This Weymouth house, situated approximately 26 kilometres from Boston, offers easy access to major attractions such as the Freedom Trail and the JFK Presidential Library.
The 226 square metre property sleeps up to 11 guests in three bedrooms and three bathrooms, boasting a fully equipped kitchen with dishwasher, free Wi-Fi, and parking.
Plum Island Beautiful Views Weekly Summer Rental - Massachusetts
9.0 18 reviews

Plum Island Beautiful Views Weekly Summer Rental

cottage, Newbury
This renovated cottage in Newbury offers private beach access and is a 5-minute walk to the main beach, with Newburyport's shops and restaurants a 10-minute drive away.
This 74 square meter dwelling accommodates up to five guests, featuring three bedrooms, one bathroom, air conditioning, a garden, parking, and a kitchen equipped with a fridge and microwave oven, whilst also providing easy day trip access to Boston, located 1 hour away by car.
Private 2-bedroom Cabin On 75 Acres In Quaint Royalston For A Relaxing Stay - Massachusetts
No reviews

Private 2-bedroom Cabin On 75 Acres In Quaint Royalston For A Relaxing Stay

cabin, Royalston
This Royalston lodge offers convenient on-site parking and is located a 9-minute walk from Royalston State Forest and a 4-minute drive from Royalston Falls.
This family-friendly cottage provides two bedrooms, one bathroom, a fully equipped kitchen with a dishwasher, and amenities including Wi-Fi, a smart TV, and a washing machine, with proximity to Rhododendron State Park and Ellinwood Country Club.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts villas and holiday homes with jacuzzi

It S All Good Game Room Ev Charger A C - Massachusetts
No reviews

It S All Good Game Room Ev Charger A C

house, Newbury
This Plum Island holiday home offers direct beach access to Newbury Beach and is situated 40km from both the Peabody Essex Museum and The House of the Seven Gables.
The 157 square metre property boasts five bedrooms, two bathrooms, sleeps thirteen guests, and includes a fully equipped kitchen with dishwasher, a jacuzzi, and free Wi-Fi.
Mermaid House @ The Compound Beach Resort Habitat - Massachusetts
9.3 109 reviews

Mermaid House @ The Compound Beach Resort Habitat

apartment, Wareham
The Mermaid House @The Onset Beach Compound Resort - Habitat is a short walk from Onset Beach and Shell Point Beach in East Wareham, a peaceful area known for its relaxed atmosphere. This property has received excellent ratings for its location, cleanliness, and overall experience.
The house is spacious, with 102 square metres of space and the capacity to accommodate up to 8 guests. Amenities include a spa tub, a terrace, a garden, and parking, making it a perfect choice for families and groups looking for a comfortable and relaxing stay.
Hot Tub, Gym, Game Room! Luxe Estate In Longmeadow - Massachusetts
No reviews

Hot Tub, Gym, Game Room! Luxe Estate In Longmeadow

house, Longmeadow
This Longmeadow property, a seven-bedroom house, is situated 9.5km from the Eastern States Exposition and The Big E, and 16km from Bradley International Airport.
The 604 square metre residence boasts a private hot tub, swimming pool, fitness centre, and parking, comfortably accommodating up to eleven guests with four bathrooms and a fully equipped kitchen.
A Lux Family Villa 6min To Gillette Pool&gym - Massachusetts
9.8 7 reviews

A Lux Family Villa 6min To Gillette Pool&gym

house, Foxborough
This Foxborough villa is situated under 5km from Moose Hill Wildlife Sanctuary, Family Funway Foxborough, and Deborah Sampson Park, and within 10km of Gillette Stadium and Showcase Live.
The five-bedroom, four-bathroom property sleeps ten guests and boasts a private pool, in-villa dryer, and is within easy reach of local attractions, offering a smoke-free environment.
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