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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

A Timeless Retreat At Historic Crompton House - Massachusetts
Massachusetts
02/08 – 14/08
NZ$724/nighttotal: NZ$8688 (12 )

A Timeless Retreat At Historic Crompton House

2 3
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.
Bright, Coastal Mashpee Condo Near The Commons - Massachusetts
9.7 37 reviews
Massachusetts
11/09 – 13/09
NZ$1172/nighttotal: NZ$2344 (2 )

Bright, Coastal Mashpee Condo Near The Commons

2 2
apartment , Mashpee
This two-bedroom apartment is situated in Mashpee, just 3.2km from South Cape Beach and 2.1km from South Cape Beach State Park, offering easy access to the beautiful coastline and outdoor activities. It has consistently received excellent ratings for location, cleanliness, and user experience.
The 97 square metre apartment comfortably accommodates up to 6 guests and includes a fully equipped kitchen with a fridge, microwave, dishwasher, and other appliances. Enjoy the convenience of air conditioning, a private patio, free Wi-Fi, a washing machine, and a swimming pool, as well as a garden and parking.
Private Heated Pool: Family Cottage In Plymouth! - Massachusetts
10 3 reviews
Massachusetts
23/12 – 30/12
NZ$535/nighttotal: NZ$3745 (7 )

Private Heated Pool: Family Cottage In Plymouth!

2 6
cottage , Plymouth
This Plymouth holiday home is situated less than 1.6km from Plymouth Long Beach and a short drive from Plimoth Patuxet Museums, offering easy access to the coast and local historical attractions.
The 91 square metre property sleeps six guests across two bedrooms and one bathroom, boasting a private heated pool, fenced garden, Smart TVs, and a well-equipped kitchen including a dishwasher.
New Seabury Escape - Massachusetts
9.2 7 reviews
Massachusetts
11/09 – 13/09
NZ$1496/nighttotal: NZ$2992 (2 )

New Seabury Escape

2 2
house , Mashpee
This Mashpee holiday home is situated 4km from South Cape Beach State Park and within 26-29km of Heritage Museums & Gardens, Sandwich Glass Museum, and the John F. Kennedy Hyannis Museum.
This two-bedroom, two-bathroom property offers 146 square metres of living space, a private patio with pool views, a garden, free Wi-Fi, and is pet-friendly.

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

167 M² House ∙ 2 Bedrooms ∙ 4 Guests - Massachusetts
Massachusetts
19/07 – 17/10
NZ$347/nighttotal: NZ$31230 (90 )

167 M² House ∙ 2 Bedrooms ∙ 4 Guests

2 1
house , Quincy
House rental for up to 4 guests. You will be based in Quincy.
Services and facilities include a freeze, free parking and a kitchen. Take advantage of the air conditioning in this house in Quincy.
Spacious Accessible Waterfront Retreat With Hot Tub - Massachusetts
10 2 reviews
Massachusetts
10/11 – 08/12
NZ$473/nighttotal: NZ$13244 (28 )

Spacious Accessible Waterfront Retreat With Hot Tub

4 2
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.
168 M² House ∙ 3 Bedrooms ∙ 5 Guests - Massachusetts
10 2 reviews
Massachusetts
10/11 – 08/12
NZ$495/nighttotal: NZ$13860 (28 )

168 M² House ∙ 3 Bedrooms ∙ 5 Guests

3 2
house , Mashpee
This three-bedroom, two-bathroom Cape Cod house in Mashpee is situated 5.1 km from Mashpee Commons, 2 km from Johns Pond, and 14 km from Falmouth's attractions.
The 168 square metre property boasts a spacious kitchen, private backyard with dog run, basement game room, and includes the Xplorie offer providing $750 of local attraction tickets, accommodating up to four guests.
Seaside Solstice Hot Tub, Sauna 4 Bedroom - Massachusetts
10 1 review
Massachusetts
16/07 – 18/07
NZ$2456/nighttotal: NZ$4912 (2 )

Seaside Solstice Hot Tub, Sauna 4 Bedroom

1 3
house , Scituate
This Scituate holiday home is situated a 9-minute walk from Sand Hills Beach and approximately 37 kilometres from the John F. Kennedy Presidential Library and Museum.
This 265 square metre property sleeps up to 19 guests, boasting two bathrooms, a fully equipped kitchen, Wi-Fi, private parking, a hot tub, sauna, terrace, and garden.

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

5 Mi To Td Garden Quiet Medford Getaway! - Massachusetts
8.0 2 reviews
Massachusetts
03/07 – 05/07
NZ$751/nighttotal: NZ$1502 (2 )

5 Mi To Td Garden Quiet Medford Getaway!

2 2
house , Medford
This Medford house, a peaceful retreat 8km from Boston's TD Garden and within a 6-8km radius of Harvard Square, Inman Square, and the Brattle Theatre, offers easy access to major attractions.
The 121 square metre property boasts two bedrooms, two bathrooms, sleeps nine guests, and includes a fully equipped kitchen with fridge, microwave, and dishwasher, plus free Wi-Fi and parking.
Luxury 5br Home Steps To Medford Square - Massachusetts
Massachusetts
03/07 – 15/07
NZ$1995/nighttotal: NZ$23940 (12 )

Luxury 5br Home Steps To Medford Square

5 4
house , Medford
This five-bedroom house is located in Medford, 5.79 kilometres from Cambridge College and 6.60 kilometres from the Peabody Museum, with Logan Airport situated 13.99 kilometres away.
This property offers 300 square metres of living space, accommodates up to 14 guests with four bathrooms, and includes a kitchen with a fridge, microwave oven, and dishwasher, alongside on-site parking, WiFi, and an outdoor seating area.
Cambridge Base Steps To Porter Square - Massachusetts
10 1 review
Massachusetts
31/07 – 02/08
NZ$822/nighttotal: NZ$1644 (2 )

Cambridge Base Steps To Porter Square

1 2
house , Cambridge
This Cambridge holiday home is located between Porter Square and Harvard Square, offering convenient access to local attractions and public transport, with the Peabody Museum 1.9 kilometres away and Brattle Theatre nearby.
This spacious two-bedroom detached house spans 88 square meters, accommodates up to six guests, and features a separate living room, a fully equipped kitchen, air conditioning, free WiFi, a private garden, and off-site parking.
Pet-friendly Apartment, 6 Miles To Downtown - Massachusetts
10 1 review
Massachusetts
07/01 – 12/01
NZ$393/nighttotal: NZ$1965 (5 )

Pet-friendly Apartment, 6 Miles To Downtown

1 2
apartment , Revere
This pet-friendly apartment in Revere is situated approximately 1.9 kilometres from Revere Beach and within a 10.5 kilometre radius of Boston's North Station and TD Garden, as well as Old North Church and Cambridge College.
This 93 square metre holiday home offers one bedroom, one bathroom, air conditioning, a fully equipped kitchen with a dishwasher and a coffee machine, a fireplace, and free WiFi, with parking also available.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts villas and holiday homes with jacuzzi

This Romantic Cottage Is Simply A Cut Above - - Massachusetts
10 60 reviews
Massachusetts
07/01 – 12/01
NZ$622/nighttotal: NZ$3110 (5 )

This Romantic Cottage Is Simply A Cut Above -

1 2
cottage , Edgartown
This charming cottage is located in Katama, just 3km from Edgartown's historic landmarks like the Edgartown Public Library and Old Whaling Church, offering a peaceful escape from the town centre. It has received excellent user ratings for its comfort and amenities.
The cottage is a one-bedroom property with two bathrooms, covering 84 square metres and comfortably accommodating two guests. It features a fully equipped kitchen, a private garden, a terrace, a jacuzzi, and a fireplace, ensuring a relaxing and enjoyable stay.
1790 Stone Manor Farm - Massachusetts
9.9 157 reviews
Massachusetts
23/12 – 30/12
NZ$850/nighttotal: NZ$5950 (7 )

1790 Stone Manor Farm

1 6
gîte , Hopkinton
This charming gîte is located in historic Hopkinton, Massachusetts, just 72 kilometres from Boston, offering easy access to the city and surrounding attractions. The property has received excellent ratings for its location, cleanliness, and user experience.
The gîte comfortably accommodates 10 guests across 5 bedrooms and 2 bathrooms. Guests can enjoy a private pool, hot tub, and a large garden with hiking trails, as well as an outdoor fire pit for evening gatherings.
Waterfront Cottage In Summer Village With Grill - Massachusetts
Massachusetts
21/07 – 30/07
NZ$1115/nighttotal: NZ$10035 (9 )

Waterfront Cottage In Summer Village With Grill

2 3
house , Westford
This Westford property is conveniently located just 30 kilometres from Harvard Square, 47 kilometres from Peabody Museum and Inman Square, and 31 kilometres from Minute Man National Historical Park, providing easy access to a range of attractions. The surrounding area offers a peaceful and tranquil setting, perfect for a relaxing getaway.
This two-bedroom house spans 81 square metres and comfortably accommodates up to 11 guests. It features a fully equipped kitchen, a washing machine, air conditioning, a swimming pool, a jacuzzi, a fitness centre, a tennis court, and parking.
Escape To Our Cabin In The Pines In Beautiful East Falmouth On Sunny Cape Cod. - Massachusetts
10 1 review
Massachusetts
04/10 – 31/10
NZ$841/nighttotal: NZ$22707 (27 )

Escape To Our Cabin In The Pines In Beautiful East Falmouth On Sunny Cape Cod.

2 2
cabin , Falmouth
This Sun Retreats lodge is situated in East Falmouth, Cape Cod, offering convenient access to local beaches, restaurants, and the shops of Falmouth town centre, the precise distances of which are not specified.
Sleeping six guests across two bedrooms and one bathroom, this self-catering property boasts a kitchen with fridge and microwave, air conditioning, a private swimming pool and jacuzzi, plus on-site access to further pools, a games room, and a lake for boating and fishing; nearby attractions include the Cape Cod Children's Museum, Ashumet Holly Wildlife Sanctuary, Water Wizz, and Island Cove Adventures.
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