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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

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.
Sunset Cove Retreat - Massachusetts
No reviews

Sunset Cove Retreat

house, Wareham
Book this Holiday rental. You will stay in Wareham.
Services and facilities: an iron, a fridge and air conditioning. Take advantage of the pool in this house.
Shared Hot Tub: Historic Cottage, Walk To Elm Park - Massachusetts
10 26 reviews

Shared Hot Tub: Historic Cottage, Walk To Elm Park

cottage, Worcester
This charming cottage is located in Worcester, just a 1.3 kilometre walk from Mechanics Hall and a 0.8 kilometre stroll from Elm Park, making it a great base for exploring the city. It has consistently received excellent reviews from previous guests.
The cottage offers 111 square metres of space, comfortably accommodating up to four guests. It features a fully equipped kitchen, a private garden, a shared swimming pool, and a range of other amenities for a relaxing and enjoyable stay.
Cozy 2-bedroom Cabin In Campground - Massachusetts
No reviews

Cozy 2-bedroom Cabin In Campground

cabin, Falmouth
This 2-bedroom lodge is located in East Falmouth, offering proximity to the Woods Hole Ferry Terminal, Oak Bluffs Harbour, and within a short distance of Cape Cod Beaches and Old Silver Beach.
This accommodation sleeps up to 6 guests and features internet, air conditioning, a swimming pool, jacuzzi, terrace, garden, and parking, with access to campground amenities and a scenic pond.

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

Newly Renovated Single Family Home - Massachusetts
10 1 review

Newly Renovated Single Family Home

house, Springfield
This detached house is located in a quiet district of Springfield, offering convenient access to Springfield's renowned landmarks.
This accommodation for 23 guests provides complimentary high-speed Wi-Fi, free private parking, a fully equipped kitchen, two bathrooms, and a flat-screen TV, with a strictly non-smoking environment.
Modern Dog-friendly Cape Cod Cottage Near Beaches - Massachusetts
No reviews

Modern Dog-friendly Cape Cod Cottage Near Beaches

house, Bourne
This two-bedroom Cape cottage in Pocasset, Bourne, is situated less than 1 kilometre from local beaches and parks, offering convenient access to marinas and village amenities.
This dog-friendly dwelling accommodates up to five guests and features central air conditioning, a modern open-plan living area, a patio with an outdoor shower, and complimentary linens, plus $750 of daily free attraction tickets through Xplorie, including Island Cruises and Whale Watch.
Location  & Quality! Right In Town, Freshly Renovated, Near Everything U Need! - Massachusetts
9.9 151 reviews

Location & Quality! Right In Town, Freshly Renovated, Near Everything U Need!

cottage, Tisbury
This charming two-bedroom apartment is located in Tisbury, just a short walk from the ferry terminal, the main street, restaurants, and beaches. This makes it the perfect base for exploring the area and enjoying everything Tisbury has to offer. The apartment has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment offers 60 square metres of living space, comfortably accommodating up to four guests. It comes fully equipped with a kitchen, a garden, a spa, parking, air conditioning, and internet access, allowing you to relax and enjoy your time away.
Sunny Chalet Nestled In The Woods Of Ashfield - Massachusetts
9.6 23 reviews

Sunny Chalet Nestled In The Woods Of Ashfield

chalet, Ashfield
This chalet is situated in the mountains of Ashfield, within two miles of Steady Lane/Hill Cemetery and Land of Providence, with Ashfield Lake and Bullitt Reservation also within three miles. The property has received excellent ratings from previous guests.
The chalet has three bedrooms and two bathrooms, with a total floor area of 167 square metres and a capacity for nine guests. The amenities include a fully equipped kitchen, a jacuzzi, a terrace, a garden, a fitness centre, and parking, along with ski-in/ski-out access and the option of housekeeping services.

Frequently asked questions about villa rentals in Massachusetts

  • What are the must-see attractions in Massachusetts?

    Massachusetts boasts a rich history and diverse landscapes. 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 offers a glimpse into the Pilgrims' story at Plimoth Patuxet Museums. Salem is renowned for its witch history, with museums and historic sites dedicated to the Salem Witch Trials. For a different perspective, consider the cultural attractions of the Berkshires, including Tanglewood, the renowned summer home of the Boston Symphony Orchestra, and the Norman Rockwell Museum.
  • 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 surprising variety of landscapes. The Berkshires region in western Massachusetts features rolling hills and mountains, perfect for hiking and scenic drives. The coastline offers stunning beaches, from the popular shores of Cape Cod to the quieter coves of the North Shore. Extensive forests, particularly in central and western Massachusetts, provide opportunities for hiking, camping, and exploring the natural beauty of the state. It's a blend of all these, really.
  • What are the best villa rentals with a pool in Massachusetts?

  • What are some surprising and hidden attractions in Massachusetts?

    Beyond the well-known destinations, Massachusetts holds many hidden gems. The Mount Auburn Cemetery in Cambridge, while a cemetery, is a beautiful and historic landscape with stunning architecture and walking trails. The Fruitlands Museum in Harvard offers a unique blend of history, art, and nature. The charming town of Lenox in the Berkshires, with its stunning scenery and historic mansions, is another often-overlooked treasure. For a unique experience, consider exploring the abandoned cranberry bogs near Plymouth.
  • 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 experience Massachusetts culture, consider attending a local town meeting – a quintessential New England experience. Visiting farmers' markets across the state provides opportunities to interact with local producers and learn about regional specialties. Exploring the vibrant arts scene in Boston, Cambridge, or the Berkshires, by attending a performance or visiting local galleries, offers another avenue for cultural engagement. Many smaller towns host festivals and events throughout the year which are great for meeting locals.
  • 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 the major cities and attractions, but to truly appreciate the state's diversity, two weeks or more are ideal. This allows for more in-depth exploration of specific regions, such as Cape Cod or the Berkshires, and enables a slower pace to enjoy the natural beauty and cultural experiences.
  • 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, with significant temperature variations between day and night, especially during the shoulder seasons (spring and autumn). Comfortable walking shoes are essential for exploring the many historic sites and charming towns. Insect repellent is also advisable, particularly during the warmer months.
  • What are the best villa rentals with parking in Massachusetts?

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

    The John F. Kennedy Presidential Library and Museum in Boston offers unique insights into American history and politics. Numerous craft breweries across the state offer tours and tastings, providing a fun and informative experience. The many historical societies and museums throughout Massachusetts often host workshops and demonstrations related to historical crafts and traditions, such as blacksmithing or quilting. The Boston Harbor Islands offer a unique blend of history and nature, with ranger-led programs and opportunities for kayaking and hiking.
  • Are there any food festivals in Massachusetts where you can try local food?

    The Boston Seafood Festival is a popular event showcasing fresh seafood. Many towns and cities across Massachusetts host smaller, local food festivals throughout the year, often celebrating specific agricultural products or regional cuisines. Checking local event listings closer to your travel dates would be helpful to find these smaller events.
  • What seasonal natural events, such as migrations or blooming periods, occur in Massachusetts?

    Spring brings the spectacular bloom of wildflowers across the state, particularly in the Berkshires and along the coast. Autumn is renowned for its vibrant foliage, with peak colours typically appearing in October. Bird migration is a significant event, with many species passing through during spring and autumn. Whale watching tours are popular along the coast, particularly during the summer months.

Nearby regions

Best Massachusetts villas and holiday homes with a kitchen

Copleys Guest House On Lake Monomonac - Massachusetts
9.9 72 reviews

Copleys Guest House On Lake Monomonac

house, Winchendon
This Belgian Farmhouse guesthouse, near Lake Monomonac in Winchendon, Massachusetts, offers convenient access to Wachusett Mountain (32-48 km), Crotched Mountain (32-48 km), and Mount Monadnock (32 km).
The self-catering property sleeps four, featuring a queen-size bed, a sofa bed, a full kitchen with dishwasher, a bathroom with washer/dryer, and kayaks/paddleboards for summer use, plus winter activities like ice fishing and snowmobiling nearby.
Bright & Cozy Woodland Home In Foxborough - Massachusetts
No reviews

Bright & Cozy Woodland Home In Foxborough

house, Foxborough
This woodland abode in Foxborough is situated approximately 15.9 kilometres from Norwood Memorial Airport, with Brown University, Fenway Park, and the Boston Museum of Fine Arts located at a considerable distance.
This two-bedroom, two-bathroom cottage offers 14 square metres of floor area, accommodating up to 15 guests with amenities including a fridge, microwave, dishwasher, air conditioning, free WiFi, and private on-site parking.
Bring Your Pet & Visit Springfield: Westfield Home - Massachusetts
9.5 2 reviews

Bring Your Pet & Visit Springfield: Westfield Home

house, Westfield
This Westfield holiday home is situated approximately 16 kilometres from both the Eastern States Exposition and The Big E, offering convenient access to these major attractions.
The 96-square-metre property features three bedrooms, one bathroom, sleeps up to 15 guests, and includes amenities such as a microwave, dishwasher, Wi-Fi, and parking.
Walk To Swift's Beach! Classic Cottage W/ Deck - Massachusetts
9.8 6 reviews

Walk To Swift's Beach! Classic Cottage W/ Deck

cottage, Wareham
This charming cottage is situated just a short walk from Swifts Beach in Wareham, a peaceful coastal town, and is 3.8km from Tobey Hospital. The cottage has received excellent reviews from previous guests, highlighting its comfortable and convenient features.
The cottage offers 62 square meters of space, accommodating up to four guests in two bedrooms and one bathroom. It includes a fully equipped kitchen, a private garden, a spa, parking, and air conditioning, ensuring a comfortable and enjoyable stay.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts villas and holiday homes with jacuzzi

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.
Hilltown Cabin Hideaway: A River Runs Through It! - Massachusetts
10 124 reviews

Hilltown Cabin Hideaway: A River Runs Through It!

cabin, Chesterfield
This three-bedroom lodge is situated in the Hilltowns of Western Massachusetts, approximately 16km from the William Cullen Bryant Homestead and the Rivulet Trail near Cummington.
The property, boasting a hot tub and bunkhouse, sleeps four guests and offers a fully equipped kitchen, Wi-Fi, and access to a 100-acre site bordering Bronson Brook, close to the Westfield River for swimming and fishing.
Forest Ridge 8c, L - Massachusetts
No reviews

Forest Ridge 8c, L

house, Lincoln
This property is located in Lincoln, Massachusetts, just 3.8 kilometres from Minute Man National Historical Park and within a 19.3-kilometre radius of Harvard Square, Brattle Theatre, and Harvard University. This makes it a great base for exploring both the historical charm of Lincoln and the cultural attractions of nearby Cambridge.
The house offers 3 bedrooms and 3 bathrooms, comfortably accommodating up to 15 guests. It features a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a tennis court, and free Wi-Fi, providing everything you need for a relaxing and enjoyable stay.
Breathtaking Ocean Views And Hot Tub - Luxurious Coastal Escape - Massachusetts
No reviews

Breathtaking Ocean Views And Hot Tub - Luxurious Coastal Escape

house, Bourne
This beachfront residence in Pocasset, MA, provides direct ocean views and private beach access, located in a peaceful district approximately 3.5 kilometres from The Bog Tavern and local beaches.
This expansive property sleeps eight guests across four bedrooms and two and a half bathrooms, featuring a gourmet kitchen, hot tub, kayaks, and a games area, with check-out at 10:00 AM.
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