Villas and Holiday homes in Massachusetts

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Massachusetts holiday homes
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12003 Villa rentals in Massachusetts

Best Massachusetts villas and holiday homes with a pool

Among the 12003 accommodations in Massachusetts, here are the 4 best villas and holiday homes with a pool

Private Pool, Hot Tub, Minutes From Beach! - Massachusetts
No reviews

Private Pool, Hot Tub, Minutes From Beach!

house, Mashpee
This detached house in Mashpee is located a mere 3 minutes' drive from South Cape Beach, with Mashpee Commons and Popponesset Marketplace also just 10 minutes away, offering convenient access to local amenities and attractions.
This family-friendly property accommodates up to eight guests and features a private heated swimming pool and hot tub, a BBQ grill, a wood fire pit, and a finished basement for entertainment, alongside essential amenities such as WiFi and air conditioning.
3 Mi To Megansett Beach: Home W/ Pool & Game Room - Massachusetts
No reviews

3 Mi To Megansett Beach: Home W/ Pool & Game Room

house, Falmouth
This detached house in North Falmouth is situated 4.8 kilometres from Megansett Beach, 17.7 kilometres from South Cape Beach State Park, and within 27.4 kilometres of various museums and Cape Cod Gateway Airport.
This spacious 280 square metre property offers accommodation for 21 guests across 4 bedrooms and 5 bathrooms, featuring a private outdoor swimming pool, a dedicated games room, a fully equipped kitchen with modern appliances, an outdoor dining area, and complimentary Wi-Fi.
Relax & Renew At Luxury Villa With Heated Pool & Hot Tub,tennis,bikes,firepit! - Massachusetts
9.4 31 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.
Ocean's Edge With Pool, Hot Tub & Beach Access - Massachusetts
No reviews

Ocean's Edge With Pool, Hot Tub & Beach Access

house, Plymouth
This beachfront property in Plymouth provides direct ocean access and is located 13 kilometres from the Sandwich Glass Museum and Heritage Museums & Gardens.
This detached house offers four bedrooms, four bathrooms, a heated outdoor swimming pool, a hot tub, air conditioning, and free WiFi, with a floor area of 325 square metres and a guest capacity of 15.

Top cities

Best family friendly Massachusetts villas and holiday home

Among the 12003 accommodations in Massachusetts, here are the 4 best family friendly villas and holiday homes

Ping-pong Table, Beach Access: North Falmouth Home - Massachusetts
No reviews

Ping-pong Table, Beach Access: North Falmouth Home

house, Falmouth
House to rent. This accommodation is based in Falmouth.
Services and facilities include a terrace, an iron and a washing machine. Take advantage of the air conditioning in this house!
Sparkling Pond Views & Unforgettable Sunsets - Massachusetts
No reviews

Sparkling Pond Views & Unforgettable Sunsets

cottage, Sandwich
This lakeside holiday home in Sandwich is situated on Peters Pond, 2.7 kilometres from Lambert's Farm Market and 12.6 kilometres from Town Neck Beach.
This family-friendly cottage accommodates six guests with three bedrooms and one bathroom, offering essential kitchen facilities, air conditioning, and complimentary daily tickets to local attractions through the Xplorie partnership, including Island Cruises and Whale Watch.
Secluded 20 Acre 10br Ultra Contemporary Retreat - Massachusetts
10 2 reviews

Secluded 20 Acre 10br Ultra Contemporary Retreat

house, Manchester-by-the-Sea
This family-friendly villa is located in Manchester-by-the-Sea, just 5 kilometres from Singing Beach, West Beach, and Graves Beach, offering easy access to the beautiful coastline. This well-rated property has received excellent reviews from previous guests, ensuring a comfortable and enjoyable stay.
The spacious 10-bedroom villa provides ample accommodation for up to 14 guests, with a total floor area of 604 square metres. Guests can enjoy a range of amenities, including a fully equipped kitchen, a garden with barbecue facilities, a tennis court, and a terrace, perfect for relaxing and enjoying the beautiful surroundings.
Family-friendly Tisbury Escape - Walk To Town - Massachusetts
9.8 84 reviews

Family-friendly Tisbury Escape - Walk To Town

house, Tisbury
This charming house is located in Vineyard Haven, just 2.1 kilometres from Owen Park Beach and 2.7 kilometres from Tisbury Town Beach, offering easy access to the beautiful coastline. It has consistently received excellent ratings for user experience, location, and cleanliness.
This 5-bedroom home spans 167 square metres and comfortably accommodates up to 9 guests. You can enjoy a range of amenities including free bikes, a fully equipped kitchen, laundry facilities, air conditioning, and a terrace or balcony, perfect for relaxing after a day exploring Tisbury and its surroundings.

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

66 M² House ∙ 2 Bedrooms ∙ 5 Guests - Massachusetts
No reviews

66 M² House ∙ 2 Bedrooms ∙ 5 Guests

house, Bourne
This updated 2-bedroom Cape home is located in Pocasset, 0.4 kilometres from Pocasset Park, 0.5 kilometres from Barlows Landing Beach, and 0.7 kilometres from Hen's Cove Public Beach.
This family-friendly property offers 65 square metres of living space for up to 5 guests, featuring central air conditioning, a modern kitchen, and an enclosed outdoor shower, with the added benefit of $750 worth of daily free tickets to local attractions through the Xplorie partnership.
Modern Tiny Home Retreat | Pond, Woods & Sauna - Massachusetts
10 18 reviews

Modern Tiny Home Retreat | Pond, Woods & Sauna

cabin, Seekonk
This architect-designed lodge in Seekonk offers a secluded setting beside a private pond, surrounded by woods, and is located just 24 kilometres from downtown Providence.
This modern timber-clad tiny home accommodates up to three guests with a lofted king bed and daybed, featuring a full kitchen, bathroom with composting toilet, and access to pond and woodland trails, with an optional wood-fired sauna available.
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Massachusetts
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage, Sandwich
This three-bedroom holiday home in Sandwich is situated in a wooded area, just steps from Peters Pond, 2.7 kilometres from Lambert's Farm Market and 12.6 kilometres from Town Neck Beach.
This family-friendly cottage accommodates up to six guests with a queen bed and two bunk beds, offering complimentary linens, keyless entry, and a $750 daily Xplorie program for local attractions.
Sparkling Pond Views & Unforgettable Sunsets - Massachusetts
No reviews

Sparkling Pond Views & Unforgettable Sunsets

cottage, Sandwich
This waterside lodge in Sandwich is located on Peters Pond, 2.7 kilometres from Lambert's Farm Market and 12.6 kilometres from Town Neck Beach.
The 3-bedroom bungalow accommodates up to 6 guests, offering direct access to Peters Pond, complimentary linens, keyless entry, and includes $750 of daily free tickets to local attractions via the Xplorie partnership.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts villas and holiday homes with jacuzzi

Serene Lake Access And Hot Tub - Cozy Charming Escape - Massachusetts
No reviews

Serene Lake Access And Hot Tub - Cozy Charming Escape

house, Billerica
This Billerica detached house provides direct private access to Nutting Lake, located within a 64-kilometre drive of Boston and the NH Seacoast.
This family-friendly property accommodates up to 10 guests across four bedrooms and three bathrooms, featuring a hot tub, a Pac-Man arcade machine, and a modern kitchen with essential appliances.
Spacious Accessible Waterfront Retreat With Hot Tub - Massachusetts
9.7 3 reviews

Spacious Accessible Waterfront Retreat With Hot Tub

house, Orange
The Zen Waterfront Retreat is a three-bedroom house in Orange, Massachusetts, offering waterfront access with canoeing and fishing, situated approximately 34km from the Pelham Town Hall Historic District and 46km from the East Village Historic District.
This 196 square metre property boasts three bathrooms, two living rooms, sleeps up to 15 guests, includes free Wi-Fi, private parking, and air conditioning, making it ideal for families or large groups exploring the area.
325 M² House ∙ 4 Bedrooms ∙ 8 Guests - Massachusetts
No reviews

325 M² House ∙ 4 Bedrooms ∙ 8 Guests

house, Plymouth
This oceanfront bluff property in Cape Cod offers panoramic Atlantic views, situated 5.3 kilometres from Sagamore Beach and 18.5 kilometres from Plimoth Patuxet Museums.
This detached house boasts a 324 square meter floor area, accommodating up to 8 guests across 4 bedrooms and 4 bathrooms, and includes a heated swimming pool, hot tub, and a daily Xplorie ticket offer worth £600.
Luxury Log Villa With Endless Pool, Hot Tub & Expansive Grounds - Massachusetts
No reviews

Luxury Log Villa With Endless Pool, Hot Tub & Expansive Grounds

house, Edgartown
This luxury log villa is located in Edgartown, offering secluded accommodation on 0.3 hectares of landscaped grounds, within easy cycling distance of Edgartown village, State Beach and local shops.
This four-bedroom, three-bathroom residence accommodates up to eight guests and features an E2000 Endless Pool Swim Spa & Hot Tub, a wood-burning fireplace, a wood-burning stove, extensive outdoor entertaining spaces with a barbecue, and a private outdoor shower.
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