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

Hot Tub, Gym, Game Room! Luxe Estate In Longmeadow - Massachusetts
Massachusetts
27/06 – 30/06
SG$8058/nighttotal: SG$24174 (3 )

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

7 3
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.
Stay & Play In Plymouth: Spacious Home W/ Yard - Massachusetts
Massachusetts
07/01 – 12/01
SG$415/nighttotal: SG$2075 (5 )

Stay & Play In Plymouth: Spacious Home W/ Yard

4 2
house , Plymouth
This detached house in Plymouth is located approximately 8.5 kilometres from Plimoth Plantation and within driving distance of the Sandwich Glass Museum and Heritage Museums & Gardens.
This air-conditioned property offers 4 bedrooms, accommodating up to 15 guests, with a private swimming pool, Wi-Fi, and parking, alongside a kitchen equipped with a fridge, microwave, and dishwasher.
Sunset Waterfront Privacy Beach - Massachusetts
9.8 131 reviews
Massachusetts
07/01 – 12/01
SG$801/nighttotal: SG$4005 (5 )

Sunset Waterfront Privacy Beach

2 2
cottage , Newburyport
This charming waterfront cottage is situated just a short distance from the bustling centre of Newburyport, offering a tranquil escape with stunning views of the marsh. It has received excellent ratings for location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay.
The property features three bedrooms, accommodating up to six guests, and a modern kitchen equipped with a dishwasher, washer, and dryer. Guests can enjoy the private pool, relax on the beach, explore the island on bikes provided, and witness breathtaking sunsets over the water.
Waterfront Cottage In Summer Village W/ Grill - Massachusetts
Massachusetts
21/07 – 30/07
SG$834/nighttotal: SG$7506 (9 )

Waterfront Cottage In Summer Village W/ 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.

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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

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.
186 M² House ∙ 3 Bedrooms ∙ 7 Guests - Massachusetts
Massachusetts
21/06 – 23/06
SG$757/nighttotal: SG$1514 (2 )

186 M² House ∙ 3 Bedrooms ∙ 7 Guests

3 2
house , Scituate
Sunset Sanctuary, a three-bedroom house in Scituate, Massachusetts, enjoys a secluded location at the end of a private street, a short drive from Scituate's harbour and historical attractions including the Scituate Lighthouse and the Old Oaken Bucket.
This 185 square metre (1991 square feet) property sleeps nine guests comfortably, offering a spacious screened deck, a private outdoor shower, a Solo Stove fire pit, and amenities including Wi-Fi, a dishwasher, and a washer/dryer.
Charming, Updated 3 Bedroom Farmhouse Farm Stay. - Massachusetts
10 36 reviews
Massachusetts
24/07 – 26/07
SG$492/nighttotal: SG$984 (2 )

Charming, Updated 3 Bedroom Farmhouse Farm Stay.

3 2
farm , Williamsburg
This three-bedroom riverside farmhouse, near Chesterfield, Massachusetts, offers tranquil views and is 4.3km from the Brewer Brook Wildlife Management Area and within 10km of Petticoat Hill and the Silvio O. Conte National Fish and Wildlife Refuge.
Sleeping six guests, this self-catering holiday cottage boasts a fully equipped kitchen (including a dishwasher), air conditioning, a terrace, garden, parking, and Wi-Fi; barbecue facilities are available for outdoor dining, and housekeeping services are offered on request.
Cambridge Boston 3br2bth Parking W&d Subway Ac - Massachusetts
9.8 10 reviews
Massachusetts
09/07 – 10/07
SG$1462/nightfor 1 night

Cambridge Boston 3br2bth Parking W&d Subway Ac

3 2
house , Somerville
This Somerville house, located near Inman Square (a 2.2km walk), Central Square Theatre (1.9km), and MIT (2.2km), offers easy access to diverse dining and entertainment options.
This 102 square metre property boasts three bedrooms, two bathrooms, sleeps fifteen guests, and includes free Wi-Fi, private parking, and a fully equipped kitchen with a dishwasher.

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

Pet-friendly Cabin W/ Fire Pit, Bbq & Great Deck! - Massachusetts
8.9 57 reviews
Massachusetts
26/06 – 03/08
SG$419/nighttotal: SG$15922 (38 )

Pet-friendly Cabin W/ Fire Pit, Bbq & Great Deck!

2 5
cabin , Goshen
This charming cabin is situated in Williamsburg, just a short drive from Amherst and Hampshire Colleges, and within easy reach of the Eastern States Expo Center and The Big E, offering a peaceful retreat close to attractions. It consistently receives excellent ratings for its location, cleanliness, and overall experience.
The spacious cabin has two bedrooms and a bathroom, covering 67 square metres, and can comfortably accommodate up to six guests. Enjoy the convenience of a fully equipped kitchen, air conditioning, Wi-Fi, a private garden, and a spa, making it an ideal choice for a relaxing and enjoyable stay.
Steps To Holyoke Medical Center! Remote-work Hub - Massachusetts
10 2 reviews
Massachusetts
21/06 – 23/06
SG$500/nighttotal: SG$1000 (2 )

Steps To Holyoke Medical Center! Remote-work Hub

3 2
house , Holyoke
Victory Residence, a spacious Holyoke apartment, is located 16 kilometres from The Big E and Eastern States Exposition and 27 kilometres from Amherst College.
This three-bedroom, three-bathroom dwelling boasts 297 square metres of floor space, comfortably accommodating up to 11 guests and including a fully equipped kitchen, free Wi-Fi, and private parking.
Heart Of Southie - Hot Tub + Walk To Top Bars - Massachusetts
10 4 reviews
Massachusetts
03/07 – 08/07
SG$2070/nighttotal: SG$10350 (5 )

Heart Of Southie - Hot Tub + Walk To Top Bars

4 2
house , Boston
This South Boston property is situated 0.6km from Carson Beach and a short walk from popular bars and restaurants in the area.
The 167 square metre house boasts four bedrooms, three bathrooms, sleeps thirteen guests, and includes a Jacuzzi, garden, parking, and fully equipped kitchen.
Serendipity Beach Retreat Nautical Retreat - Massachusetts
Massachusetts
21/06 – 23/06
SG$485/nighttotal: SG$970 (2 )

Serendipity Beach Retreat Nautical Retreat

1 3
house , Salisbury
This Salisbury Beach flat offers direct access to the beach and is located 5 kilometres from the Casino Ballroom, with Peabody Essex Museum and The House of the Seven Gables situated 45 kilometres away.
This 56 square metre, two-bedroom apartment accommodates up to seven guests and includes a fully equipped kitchen with a dishwasher and oven, air conditioning, free WiFi, and on-site parking.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts villas and holiday homes with jacuzzi

Escape To Our Cabin In The Pines In Beautiful East Falmouth On Sunny Cape Cod. - Massachusetts
10 1 review
Massachusetts
21/07 – 30/07
SG$654/nighttotal: SG$5886 (9 )

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

2 3
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.
Fisherman's Paradise - Massachusetts
Massachusetts
07/01 – 12/01
SG$988/nighttotal: SG$4940 (5 )

Fisherman's Paradise

1 2
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.
4br Retreat W Hot Tub Fire Pit & Game Room - Massachusetts
Massachusetts
07/01 – 12/01
SG$1680/nighttotal: SG$8400 (5 )

4br Retreat W Hot Tub Fire Pit & Game Room

4 2
house , Falmouth
This 4-bedroom holiday home in Falmouth is situated approximately 13 kilometres from the Sandwich Glass Museum and Heritage Museums & Gardens, and 13 kilometres from South Cape Beach State Park.
This spacious property offers accommodation for 16 guests with 4 bedrooms and 5 bathrooms, featuring a well-equipped kitchen with a dishwasher and microwave, air conditioning, a private hot tub, a game room, and a fire pit, with parking available.
Private Pool Hot Tub Minutes From Beach - Massachusetts
Massachusetts
04/10 – 31/10
SG$737/nighttotal: SG$19899 (27 )

Private Pool Hot Tub Minutes From Beach

1 2
house , Mashpee
This spacious holiday home in Mashpee is situated mere minutes from the beach, offering convenient seaside access.
With a generous floor area of 281 square meters, this residence accommodates up to 15 guests across four bedrooms, featuring a fully equipped kitchen, air conditioning, a private swimming pool, hot tub, garden, and on-site parking.
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