Villas and Holiday homes in Massachusetts

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Massachusetts villas
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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 Lux Family Villa 6min To Gillette Pool&gym - Massachusetts
9.8 7 reviews
Massachusetts
14/09 – 16/09
SG$2326/nighttotal: SG$4652 (2 )

A Lux Family Villa 6min To Gillette Pool&gym

5 2
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.
Bostonarea Executive Estate For 31 Days W Pool - Massachusetts
Massachusetts
10/11 – 07/01
SG$2381/nighttotal: SG$138098 (58 )

Bostonarea Executive Estate For 31 Days W Pool

8 2
house , Dedham
This Dedham Luxe Grand Colonial property, situated approximately 16-19 kilometres from Boston attractions including the Museum of Fine Arts, Fenway Park, Boston University, and the Hynes Convention Centre, offers a luxurious stay.
This five-bathroom, one-bedroom residence boasts a 763 square metre floor area, accommodating up to 16 guests and featuring a private pool, free parking, and a fully equipped kitchen; washer/dryer and Wi-Fi are also included.
Pool, Gym & Game Room: Expansive Falmouth Retreat! - Massachusetts
Massachusetts
04/10 – 31/10
SG$937/nighttotal: SG$25299 (27 )

Pool, Gym & Game Room: Expansive Falmouth Retreat!

3 2
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.
The Creation Station Is A Cozy Place So Make Yourself At Home. - Massachusetts
9.9 640 reviews
Massachusetts
23/06 – 25/06
SG$320/nighttotal: SG$640 (2 )

The Creation Station Is A Cozy Place So Make Yourself At Home.

1 2
apartment , Easthampton Town
The Creation Station bungalow is situated in Easthampton, just a short distance from the town's cultural district, offering easy access to breweries, music venues, and art markets. This charming property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The bungalow is a spacious one-room property spanning 149 square metres, offering a bright and airy atmosphere thanks to its numerous windows. Amenities include a swimming pool, jacuzzi, spa, and a garden, with a unique entertainment hub featuring a stage, sound system, and karaoke facilities.

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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

Multi-level Marion House: Loft, Deck + Ocean Views - Massachusetts
9.6 57 reviews
Massachusetts
10/11 – 07/01
SG$488/nighttotal: SG$28304 (58 )

Multi-level Marion House: Loft, Deck + Ocean Views

5 2
house , Marion
This five-bedroom house is located just six kilometres from Hollywoods Beach, Ned's Point Lighthouse and East Over Reservation, offering easy access to a range of attractions. The property has received excellent ratings for location, cleanliness and overall user experience.
This spacious home spans 260 square metres and comfortably accommodates eight guests. Amenities include a fully equipped kitchen, air conditioning, a terrace, a garden, a bar, parking and free Wi-Fi in public areas.
Renovated Cottage With Nice Yard And Homey Interior - Massachusetts
9.0 41 reviews
Massachusetts
31/08 – 07/09
SG$543/nighttotal: SG$3801 (7 )

Renovated Cottage With Nice Yard And Homey Interior

3 2
cottage , Edgartown
This charming cottage is located just 3.2 kilometres from the centre of Edgartown, near Sengekontacket Pond, offering a peaceful retreat close to the island's attractions. It has received very good reviews from previous guests.
The cottage has two bedrooms and one bathroom, covering 93 square metres, and can accommodate up to eight guests. The cottage offers a fully equipped kitchen, a private garden, a terrace, and a parking space, making it perfect for families and groups looking for a comfortable and convenient stay.
The Fairview - North Of Boston Furnished Home - Massachusetts
9.9 17 reviews
Massachusetts
09/07 – 10/07
SG$530/nightfor 1 night

The Fairview - North Of Boston Furnished Home

3 2
house , Peabody
This Peabody dwelling is situated 7.4 kilometres from the Peabody Essex Museum and 8 kilometres from The House of the Seven Gables.
This spacious holiday home offers 135 square metres of living space with three bedrooms, two bathrooms, and accommodation for seven guests, featuring a fully equipped kitchen, entertainment systems, and access to a fitness centre, tennis court, and outdoor fireplace.
New 9br6bth Parking Mit Harvard Boston Walk To T - Massachusetts
Massachusetts
09/07 – 10/07
SG$6384/nightfor 1 night

New 9br6bth Parking Mit Harvard Boston Walk To T

9 2
house , Somerville
This Somerville house, near Inman Square, offers easy access to the T subway and is less than 2.4 kilometres from both the Massachusetts Institute of Technology (MIT) and Cambridge College.
This nine-bedroom, six-bathroom property boasts 232 square metres of floor space, comfortably accommodating 42 guests and including a fully equipped kitchen, three living rooms, parking, and a balcony.

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

Hot Tub, Gym, Game Room! Luxe Estate In Longmeadow - Massachusetts
Massachusetts
27/06 – 04/07
SG$7826/nighttotal: SG$54782 (7 )

Hot Tub, Gym, Game Room! Luxe Estate In Longmeadow

7 8
house , Longmeadow
This Longmeadow property, a seven-bedroom house, is situated 9.5km from the Eastern States Exposition and The Big E, and 16km from Bradley International Airport.
The 604 square metre residence boasts a private hot tub, swimming pool, fitness centre, and parking, comfortably accommodating up to eleven guests with four bathrooms and a fully equipped kitchen.
Massachusetts Vacation Rental: 5 Mi To Fall River - Massachusetts
8.4 5 reviews
Massachusetts
23/06 – 25/06
SG$422/nighttotal: SG$844 (2 )

Massachusetts Vacation Rental: 5 Mi To Fall River

2 2
house , Somerset
This Somerset holiday home is situated 8km from Fall River, offering easy access to Brown, Johnson & Wales Universities and the Rhode Island School of Design Museum of Art, all within a 26km radius.
The 107 square metre property boasts two bedrooms, one bathroom, sleeping up to 11 guests, and features a fully equipped kitchen, free Wi-Fi, a fireplace, and air conditioning.
Spacious 3br Sunset Island Beach House - Massachusetts
10 2 reviews
Massachusetts
27/06 – 30/06
SG$735/nighttotal: SG$2205 (3 )

Spacious 3br Sunset Island Beach House

3 3
house , Wareham
This spacious Sunset Island Beach House in Wareham offers a prime location, a 4-minute walk from Shell Point Beach and within 19 kilometres of both the Sandwich Glass Museum and Heritage Museums & Gardens.
The 121-square-metre property boasts three bedrooms, two bathrooms, and can accommodate up to 15 guests, featuring a fully equipped kitchen, free Wi-Fi, a terrace, and private parking; pets are welcome (charges apply).
Sherizee Home - Massachusetts
10 2 reviews
Massachusetts
24/07 – 26/07
SG$673/nighttotal: SG$1346 (2 )

Sherizee Home

3 2
house , Marblehead
Sherizee Home, a three-bedroom house in Marblehead, Massachusetts, is conveniently located near Riverhead, Devereux, and Gas House beaches, and is approximately 6.3 km from Salem's historic sites including the Peabody Essex Museum and The House of the Seven Gables.
This 142 square metre property offers a spacious layout sleeping up to 11 guests, boasting a fully equipped kitchen with fridge, microwave, and dishwasher, free Wi-Fi, private parking, and towels and bed linen provided.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts villas and holiday homes with jacuzzi

Lakeview Getaway With Hot Tub - Massachusetts
Massachusetts
16/07 – 18/07
SG$796/nighttotal: SG$1592 (2 )

Lakeview Getaway With Hot Tub

3 3
house , Billerica
This Billerica holiday home is situated an 8-minute walk from Micozzi Beach, 16 km from Minute Man National Historical Park, and 24 km from the Brattle Theatre.
The 130 square metre property boasts three bedrooms, two bathrooms, sleeps up to 15 guests, and includes a fully equipped kitchen, Jacuzzi, terrace, garden, free Wi-Fi, parking, and barbecue facilities; nearby attractions include a casino and fishing opportunities.
Escape To Our Cabin In The Pines In Beautiful East Falmouth On Sunny Cape Cod. - Massachusetts
10 1 review
Massachusetts
04/10 – 31/10
SG$628/nighttotal: SG$16956 (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.
1790 Stone Manor Farm - Massachusetts
9.9 157 reviews
Massachusetts
23/12 – 30/12
SG$635/nighttotal: SG$4445 (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 W/ Grill - Massachusetts
10 1 review
Massachusetts
21/07 – 30/07
SG$868/nighttotal: SG$7812 (9 )

Waterfront Cottage In Summer Village W/ Grill

2 3
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.
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