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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

Weymouth Waterfront Getaway W/ Swim Spa & Hot Tub - Massachusetts
9.8 5 reviews

Weymouth Waterfront Getaway W/ Swim Spa & Hot Tub

house, Weymouth Town
This beachfront property in Weymouth is just 8 kilometres from the JFK Presidential Library & Museum and a short walk from Wessagusset Beach, offering a peaceful and convenient location for exploring the area. The property has received excellent ratings for its cleanliness, location, and overall experience.
The house provides comfortable accommodation for up to 9 guests across 3 bedrooms and 3 bathrooms, spanning 144 square metres. Guests can enjoy a range of amenities, including a private pool and hot tub, a fully equipped kitchen, and free Wi-Fi, making it ideal for a relaxing and enjoyable stay.
Shared Hot Tub: Historic Cottage, Walk To Elm Park - Massachusetts
9.0 6 reviews

Shared Hot Tub: Historic Cottage, Walk To Elm Park

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.
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.
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.

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

Ob Cozy-cottage-glam Off Circuit With Great Outdoor Living - Massachusetts
9.6 11 reviews

Ob Cozy-cottage-glam Off Circuit With Great Outdoor Living

cottage, Oak Bluffs
This Oak Bluffs holiday home is situated a 15-minute walk (approx. 1.2km) from Circuit Avenue and Inkwell Beach, and 10 minutes (approx. 0.8km) from the Cottage Museum and Trinity Park Tabernacle.
The two-bedroom, two-bathroom property sleeps five, offering a fully equipped kitchen, patio, garden with barbecue, Smart TV, and free Wi-Fi; nearby activities include exploring the historic beach and browsing the shops and restaurants on Circuit Avenue.
Relax By The Lake - Cozy Lakefront Retreat With Scenic Views - Massachusetts
9.8 14 reviews

Relax By The Lake - Cozy Lakefront Retreat With Scenic Views

cottage, Charlton
This lakeside retreat in Charlton, Massachusetts, is situated on Cranberry Meadow Pond, under 6.4 kilometres from Treehouse Brewery.
This two-bedroom, two-bathroom holiday home offers 78 square metres of living space, including an open-plan living area with a gas fireplace, a spacious deck with water views, and access to kayaks and canoes for exploring the pond; it sleeps six guests comfortably.
Winery Bungalow W/ Vineyard Views & Wine Tasting - Massachusetts
9.9 188 reviews

Winery Bungalow W/ Vineyard Views & Wine Tasting

gîte, North Andover
This charming bungalow is situated in the picturesque Marble Ridge Farm neighbourhood of North Andover, just a short drive from the centre of Andover and within easy reach of major highways, hiking trails, beaches, and nearby cities like Boston, Salem, and Portsmouth. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The cosy cottage has one bedroom and one bathroom, comfortably accommodating up to four guests. It features a modern kitchen, a spacious living area, a private patio, and access to an adults-only pool and a wine tasting at the on-site Marble Ridge Winery, making it perfect for a relaxing getaway.
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.

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

Hot Tub, Electric Bikes, Solo Stove, Projector, Smores - Massachusetts
9.0 24 reviews

Hot Tub, Electric Bikes, Solo Stove, Projector, Smores

house, Marblehead
This charming three-bedroom house is situated just 2.6 kilometres from Gas House Beach and 7.6 kilometres from the Peabody Essex Museum, offering a peaceful escape in the heart of Marblehead. The property has received excellent ratings for location, cleanliness and overall user experience, making it an ideal choice for your stay.
The house spans 279 square metres and comfortably accommodates up to 10 guests. Enjoy a range of amenities including a private hot tub, electric bikes, a fire pit, a projector, stunning sea views, a fully equipped kitchen, outdoor dining, free parking, and close proximity to Marblehead's top attractions.
121 M² House ∙ 3 Bedrooms ∙ 6 Guests - Massachusetts
No reviews

121 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Newton
House listing for up to 6 guests. You will be in Newton.
Services and facilities: a fridge, a freeze and a washing machine. This house in Newton also has air conditioning!
Menauhant Beach Paradise - Massachusetts
No reviews

Menauhant Beach Paradise

house, Falmouth
This one-bedroom holiday let in Falmouth is a six-minute walk to Menauhant Beach and within 30 kilometres of the Heritage Museums & Gardens and the John F Kennedy Hyannis Museum.
This holiday let offers air conditioning, a sauna, free Wi-Fi, and private parking, with a fully equipped kitchen, three bathrooms, and capacity for 23 guests.
Rustic-chic Cottage W/ Yard & Grill - Near Hiking! - Massachusetts
9.7 35 reviews

Rustic-chic Cottage W/ Yard & Grill - Near Hiking!

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.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts villas and holiday homes with jacuzzi

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.
A Timeless Retreat At Historic Crompton House - Massachusetts
No reviews

A Timeless Retreat At Historic Crompton House

house, Worcester
This holiday home is situated in Worcester, a short walk from Worcester Polytechnic Institute and the DCU Centre Arena & Convention Centre, and 1.8 kilometres from Worcester, MA Station.
This property offers 158 square metres of living space for up to 7 guests, featuring 2 bedrooms, 2 bathrooms, air conditioning, an outdoor swimming pool, a hot tub, and a well-equipped kitchen.
Pocasset Family Retreat Ocean View - Massachusetts
No reviews

Pocasset Family Retreat Ocean View

house, Bourne
This Pocasset ocean-view holiday home in Bourne, Massachusetts, is situated approximately 22.5 kilometres from both the Sandwich Glass Museum and Heritage Museums & Gardens.
The 196 square metre property boasts one bedroom, one bathroom, sleeps eleven guests, and includes a fully equipped kitchen, Jacuzzi, garden, parking, Wi-Fi, and air conditioning.
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.
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