Villas and Holiday homes in Massachusetts

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Massachusetts villas
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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

88 Ashumet Road - Massachusetts
No reviews

88 Ashumet Road

house, Falmouth
This East Falmouth property, situated on a quiet cul-de-sac bordering conservation land, offers convenient access to beaches such as Falmouth Heights, Old Silver, and Surf Drive Beach, all within 11 kilometres, and is close to downtown Falmouth and Mashpee Commons.
This detached house for 7 guests features 4 bedrooms, 2 bathrooms, air conditioning, a private heated pool (July-Labour Day), a fenced garden, Wi-Fi, a fully equipped kitchen, and a dedicated study, with nearby attractions including the Shining Sea Bikeway, Falmouth Ice Arena (6 kilometres away), and ferry services to Martha's Vineyard and Nantucket.
Pool, Gym & Game Room: Expansive Falmouth Retreat! - Massachusetts
No reviews

Pool, Gym & Game Room: Expansive Falmouth Retreat!

house, Falmouth
This Falmouth holiday home is located just 32km from both the Sandwich Glass Museum and Heritage Museums & Gardens, offering easy access to these attractions and the surrounding area. The house is situated in a quiet residential area, providing a peaceful retreat from the hustle and bustle of the town.
The property spans 303 square metres and comfortably accommodates up to 10 guests, making it ideal for families or groups of friends. It features a well-equipped kitchen, three bedrooms, three bathrooms, a private pool, a gym, and a games room, ensuring a comfortable and enjoyable stay.
House ∙ 4 Bedrooms ∙ 1 Guest - Massachusetts
No reviews

House ∙ 4 Bedrooms ∙ 1 Guest

house, Avon
This detached house in Avon provides ample space with 4 bedrooms and 5 bathrooms, featuring a private swimming pool, a terrace, a balcony, and a garage for parking.
Guests can enjoy a fully-equipped kitchen with a dishwasher, air conditioning, and a BBQ grill, with the property being suitable for families and offering easy access to local amenities and outdoor pursuits a short drive away.
Waterfront Cottage In Summer Village W/ Grill - Massachusetts
10 2 reviews

Waterfront Cottage In Summer Village W/ Grill

cottage, Westford
This charming cottage is located in Westford's Summer Village district, a short 7-minute drive (4.4km) from Westford Town Common and a 13-minute drive (8.1km) from Kimball Farm. The cottage offers a peaceful retreat with easy access to local attractions.
The 81 square metre property sleeps up to six guests and features two bedrooms and one bathroom. This comfortable holiday home comes with a fully equipped kitchen, a private outdoor area with a barbecue, and access to a shared swimming pool and jacuzzi.

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

Entire 3 Story Brownstone Building, Walk To Fenway - Massachusetts
10 173 reviews

Entire 3 Story Brownstone Building, Walk To Fenway

house, Boston
This 7-bedroom house is conveniently located in the Fenway–Kenmore district, just a short walk from Fenway Park, Boston University, and the Longwood Medical Area. This property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The spacious 372 square metre house comfortably accommodates up to 16 guests. Enjoy access to a fully equipped kitchen, a private patio, and a garden, ideal for relaxing after a day exploring the city.
Walk To Buzzards Bay Beach: Spacious Onset Home - Massachusetts
9.9 15 reviews

Walk To Buzzards Bay Beach: Spacious Onset Home

house, Wareham
This Onset property, near Buzzards Bay and 18km from Heritage Museums & Gardens and the Sandwich Glass Museum, offers a spacious family-friendly home. This five-bedroom, three-bathroom dwelling boasts a 186 square metre floor area, a Jacuzzi, spa, and private garden, sleeping up to ten guests, with free Wi-Fi and parking.
130 M² House ∙ 3 Bedrooms ∙ 12 Guests - Massachusetts
No reviews

130 M² House ∙ 3 Bedrooms ∙ 12 Guests

house, Wareham
This spacious Cape Cod-style house is located in Wareham's Swift's Beach neighbourhood, 0.8km from the ocean and an hour's drive from Boston, Providence, and Newport.
The 130 square metre property sleeps 12, boasts three bedrooms, one bathroom, a fully equipped kitchen with dishwasher, and offers a large fenced garden, multiple decks, and outdoor amenities including a shower and barbecue.
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.

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 visit to Plymouth, with its Pilgrim Monument and Plimoth Patuxet Museums, is essential. Boston is a must, offering iconic sites like Faneuil Hall Marketplace, the Freedom Trail, and the Boston Tea Party Ships & Museum. Further afield, Salem's maritime history and witch trial legacy are captivating, and the Berkshires offer stunning natural beauty and cultural institutions like Tanglewood.
  • What are the best villa rentals in Massachusetts?

    Among the villa rentals in Massachusetts, Luxurious Harbor View "Millie" 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 is mountainous, perfect for hiking and scenic drives. The coastline features beautiful beaches, particularly on Cape Cod and the islands of Nantucket and Martha's Vineyard. Extensive forests are found throughout the state, particularly in central and western Massachusetts, providing opportunities for hiking and outdoor recreation. You'll also find charming coastal towns and bustling 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, explore the charming town of Lenox in the Berkshires, known for its beautiful scenery and cultural attractions like the Norman Rockwell Museum. The Mount Greylock State Reservation, home to the highest peak in Massachusetts, offers incredible hiking trails and panoramic views. Consider a visit to the Fruitlands Museum in Harvard, showcasing Shaker history and stunning landscapes. The charming coastal town of Rockport is also a delightful surprise.
  • 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?

    Attend a local farmers' market – many towns have weekly markets showcasing local produce and crafts. Visit a historical society or museum and chat with the staff and volunteers. Consider taking a cooking class focusing on New England cuisine. Exploring the many independent bookstores and engaging with the staff can provide insights into local culture and literature. Attending a performance at a local theatre or music venue can offer a vibrant cultural experience.
  • 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, focusing on a specific region like Boston and its surroundings or Cape Cod. To truly experience the diversity of the state, including the Berkshires and the islands, two weeks or more would be ideal, allowing for a more relaxed pace and deeper exploration.
  • 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, pack layers! Massachusetts weather can be unpredictable, even in summer. Comfortable walking shoes are essential, as much of the exploration involves walking. Insect repellent, especially for summer months, is advisable, particularly when exploring the forests and coastal areas. A reusable water bottle is also highly recommended.
  • What are the best villa rentals with parking in Massachusetts?

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

    Consider a glassblowing workshop at a local studio. Many towns offer pottery or painting classes. The Boston area has numerous opportunities for historical reenactments and walking tours focusing on specific aspects of the city's history. Look for workshops on traditional New England crafts like quilting or basket weaving.
  • Are there any food festivals in Massachusetts where you can try local food?

    The Topsfield Fair is a large agricultural fair with numerous food options. Many towns and cities host smaller, seasonal food festivals celebrating local produce and cuisine. Check local event listings for specific dates and locations. The Boston Harborfest is a summer event with food stalls offering a taste of local fare.
  • What seasonal natural events, such as migrations or blooming periods, occur in Massachusetts?

    Spring brings the blooming of wildflowers, particularly in the Berkshires and other forested areas. Autumn is renowned for its spectacular foliage, with peak colours typically appearing in October. Bird migration is noticeable in spring and autumn, with various species passing through the state.
  • What exclusive experiences are available when visiting Massachusetts?

    A private tour of a historic home or estate offers an intimate look into Massachusetts's past. Consider a whale watching tour from a coastal town like Provincetown or Gloucester. A private cooking class focusing on regional specialities provides a unique cultural immersion. A hot air balloon ride over the Berkshires offers breathtaking views of the landscape.

Nearby regions

Best Massachusetts villas and holiday homes with a kitchen

Oceanfront Cape Cod Home W/ Porch, Yard + Grill! - Massachusetts
9.8 41 reviews

Oceanfront Cape Cod Home W/ Porch, Yard + Grill!

house, Marshfield
This Marshfield oceanfront property, a short 1.8km drive from both Duxbury Beach and Fieldston Beach, offers stunning sea views.
The 114 square metre house boasts two bedrooms, two bathrooms, a fully equipped kitchen including a dishwasher, and a terrace overlooking the ocean; free Wi-Fi, parking and bicycle use are also provided.
Cozy 3br Cottage With Lambert's Cove Beach Access - Massachusetts
10 1 review

Cozy 3br Cottage With Lambert's Cove Beach Access

cottage, West Tisbury
This West Tisbury holiday home is situated near Grey Barn, offering easy access to Lambert's Cove Beach (beach pass required) and proximity to attractions such as Polly Hill Arboretum and Chilmark Chocolates.
Sleeping six guests across three bedrooms and three bathrooms, the property boasts a fully equipped kitchen, outdoor dining areas, a firepit, and outdoor shower; upcoming renovations (April 2025) include a new air conditioning system and a fresh coat of paint.
Cozy Town Neck Cape Escape – Pet Friendly - Massachusetts
No reviews

Cozy Town Neck Cape Escape – Pet Friendly

house, Sandwich
This Old Harbor House property in Sandwich is a short 1km walk from Town Neck Beach and within a few kilometres of the Sandwich Glass Museum and Heritage Museums & Gardens.
The self-catering house sleeps eleven guests across one bedroom and one bathroom, offering amenities such as Wi-Fi, air conditioning, a fully equipped kitchen with fridge and microwave, and a TV.
Winery Farmhouse W/ Private Hot Tub & Wine Tasting - Massachusetts
9.9 128 reviews

Winery Farmhouse W/ Private Hot Tub & Wine Tasting

gîte, North Andover
The Ice House is a luxurious apartment located on the Marble Ridge Farm estate in North Andover, a short drive from Harold Parker State Forest, Ipswich River Wildlife Sanctuary, and Crane Beach. The property is highly rated for location, cleanliness, and overall user experience.
The apartment has three bedrooms, one bathroom, and can accommodate up to seven guests. Guests can enjoy complimentary wine tastings, access to a swimming pool, a patio, and a private garden, as well as a fully equipped kitchen and modern amenities.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts villas and holiday homes with jacuzzi

Tranquil Lakeview Escape With Hot Tub - Cozy And Inviting Retreat - Massachusetts
No reviews

Tranquil Lakeview Escape With Hot Tub - Cozy And Inviting Retreat

house, Billerica
This Billerica residence offers direct access to Nutting Lake, featuring a public beach for swimming and fishing, and is located approximately 800 metres from Billerica Centre's shops and restaurants, with easy access to Routes 3 and I-95, as well as the Billerica Purple Line Commuter Rail.
This family-friendly holiday home comfortably accommodates up to eight guests across three queen bedrooms and a sofa bed, boasting a modern kitchen with stainless steel appliances, a hot tub and BBQ grill in the private garden, and fast Wi-Fi suitable for remote working.
Luxury Villa Heated Indoor Pool - Massachusetts
9.9 17 reviews

Luxury Villa Heated Indoor Pool

house, Easton
This luxurious flat is located in a refined district of Easton, offering convenient access to local landmarks.
This spacious accommodation sleeps up to 10 guests, featuring three en-suite bedrooms, a stylish entertainment room with extra sleeping capacity, and an indoor heated saltwater swimming pool, with parking and internet provided.
Fisherman's Paradise - Massachusetts
No reviews

Fisherman's Paradise

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.
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.
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