Search Massachusetts villas and holiday homes

10727 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • bookabach
  • expedia
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelscom
  • hotelopia
Massachusetts holiday homes
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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

Shared Hot Tub Historic Cottage, Walk To Elm Park - Massachusetts
9.0 5 reviews
Massachusetts
31/08 – 07/09
NZ$627/nighttotal: NZ$4389 (7 )

Shared Hot Tub Historic Cottage, Walk To Elm Park

2 2
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.
Waterfront Cottage In Summer Village W/ Grill - Massachusetts
10 1 review
Massachusetts
21/07 – 30/07
NZ$1161/nighttotal: NZ$10449 (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.
A Timeless Retreat At Historic Crompton House - Massachusetts
Massachusetts
03/07 – 15/07
NZ$521/nighttotal: NZ$6252 (12 )

A Timeless Retreat At Historic Crompton House

2 4
house , Worcester
This historic Crompton House is situated in a convenient Worcester district, offering direct access to Mechanics Hall and Hanover Theatre, and is under an hour by train to Boston.
This 2-bedroom, 2-bathroom dwelling accommodates up to 4 guests and features a private garden, shared swimming pool and hot tub, wood-burning fireplaces, on-site parking, and an espresso machine, with easy access to Worcester Public Market and Polar Park.
Shared Hot Tub: Historic Cottage, Walk To Elm Park - Massachusetts
10 24 reviews
Massachusetts
16/07 – 18/07
NZ$644/nighttotal: NZ$1288 (2 )

Shared Hot Tub: Historic Cottage, Walk To Elm Park

2 3
cottage , Worcester
This charming cottage is located in Worcester, just a 1.3 kilometre walk from Mechanics Hall and a 0.8 kilometre stroll from Elm Park, making it a great base for exploring the city. It has consistently received excellent reviews from previous guests.
The cottage offers 111 square metres of space, comfortably accommodating up to four guests. It features a fully equipped kitchen, a private garden, a shared swimming pool, and a range of other amenities for a relaxing and enjoyable stay.

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

Presidents - Massachusetts
9.3 25 reviews
Massachusetts
14/09 – 16/09
NZ$659/nighttotal: NZ$1318 (2 )

Presidents

4 2
house , Plymouth
This four-bedroom house is situated in a peaceful residential area of Plymouth, just 7.4 kilometres from Plimoth Plantation and 24 kilometres from both Heritage Museums & Gardens and Sandwich Glass Museum. The property has consistently received excellent ratings for its cleanliness, location and overall experience.
The 114 square metre home offers ample space for families or groups, with a fully equipped kitchen, living room, dining area and two bathrooms. Guests can enjoy a range of amenities, including free Wi-Fi, air conditioning, a terrace, a garden, parking, and a picnic area, as well as access to nearby hiking trails.
Onset Beach, Cape Code , Blackmore Pond, Private Waterfront Cottage - Massachusetts
9.7 196 reviews
Massachusetts
04/10 – 31/10
NZ$506/nighttotal: NZ$13662 (27 )

Onset Beach, Cape Code , Blackmore Pond, Private Waterfront Cottage

2 2
cottage , Wareham
This charming waterfront cottage is located in Wareham, just a short drive from Tobey Hospital, Swifts Beach, Water Wizz, and Lyman Reserve, offering easy access to attractions and activities. The cottage has consistently received excellent ratings for its cleanliness, location, and overall experience.
The two-bedroom cottage provides comfortable accommodation for up to four guests, with a spacious 74 square meters of living space. Enjoy a range of amenities including a private pool, a terrace, a garden, and free Wi-Fi, perfect for relaxing and enjoying the beautiful surroundings.
Seaside Solstice Hot Tub, Sauna 4 Bedroom - Massachusetts
10 1 review
Massachusetts
27/06 – 30/06
NZ$2361/nighttotal: NZ$7083 (3 )

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.
Enchanting Hidden Door Escape - Massachusetts
9.0 7 reviews
Massachusetts
24/07 – 27/07
NZ$1121/nighttotal: NZ$3363 (3 )

Enchanting Hidden Door Escape

4 2
house , Stoneham
This Stoneham home is conveniently located just 13.4 kilometres from Cambridge College and 14.6 kilometres from Inman Square, offering easy access to the area's attractions. The property has received very good user and location ratings, and a good cleanliness rating.
The 4-bedroom house provides 139 square metres of space, comfortably accommodating up to 10 guests. The property offers a range of amenities including air conditioning, a dishwasher, a kettle, and a hairdryer, as well as a private garden and free parking.

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

Waterfront Comfy 2bd Cottage W/ Direct Access To Private Beach & Amazing Bayview - Massachusetts
9.8 6 reviews
Massachusetts
10/11 – 07/01
NZ$512/nighttotal: NZ$29696 (58 )

Waterfront Comfy 2bd Cottage W/ Direct Access To Private Beach & Amazing Bayview

2 2
cottage , Wareham
This Wareham holiday home is situated near Onset Beach and Shell Point Beach, within 5km of the Porter Thermometer Museum and Lyman Reserve.
The two-bedroom property sleeps six, boasting a fully equipped kitchen, three bathrooms, air conditioning, a swimming pool, garden, parking, Wi-Fi and a DVD player, with a nearby water park offering additional entertainment.
3 Bed 2 Bath Vacation Home In West Tisbury - Massachusetts
9.0 37 reviews
Massachusetts
03/07 – 15/07
NZ$1153/nighttotal: NZ$13836 (12 )

3 Bed 2 Bath Vacation Home In West Tisbury

1 4
house , West Tisbury
This West Tisbury holiday home is situated 7km from Martha's Vineyard Airport and 19km from Edgartown Lighthouse, offering a peaceful retreat in a convenient location.
Sleeping three guests, this self-catering property boasts three bedrooms, two bathrooms, a well-equipped kitchen with dishwasher, and a private garden with outdoor dining area; free Wi-Fi is also available.
Tumbleinn - Massachusetts
Massachusetts
26/06 – 28/06
NZ$1379/nighttotal: NZ$2758 (2 )

Tumbleinn

2 2
house , Oak Bluffs
TumbleINN is a holiday cottage located in Oak Bluffs, 1.2 kilometres from Oak Bluffs Town Beach and 10.9 kilometres from Edgartown Lighthouse.
This 52 square metre property offers accommodation for up to 7 guests, featuring a kitchen equipped with a fridge and microwave oven, 1 bathroom, and an on-site restaurant, with opportunities for cycling and an outdoor dining area.
Nothing Fancy Older Pet Friendly Home Near I 95 - Massachusetts
Massachusetts
16/07 – 23/07
NZ$700/nighttotal: NZ$4900 (7 )

Nothing Fancy Older Pet Friendly Home Near I 95

3 7
house , Georgetown
This pet-friendly Georgetown holiday home, near the I-95 highway, is conveniently located 27 kilometres from both the Peabody Essex Museum and the House of the Seven Gables.
This three-bedroom property boasts a 930 square metre floor area, accommodating up to 15 guests, and features a fully equipped kitchen, air conditioning, a terrace, garden, and free Wi-Fi.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts villas and holiday homes with jacuzzi

Private Hot Tub, Yard & Games Galore: Plymouth Gem - Massachusetts
Massachusetts
31/08 – 07/09
NZ$707/nighttotal: NZ$4949 (7 )

Private Hot Tub, Yard & Games Galore: Plymouth Gem

4 2
house , Plymouth
This detached house in Plymouth is located within 11 kilometres of Plimoth Plantation and 37 kilometres from the Sandwich Glass Museum and Heritage Museums & Gardens.
This spacious residence offers 161 square meters of living space with four bedrooms, accommodating up to 15 guests, and features a private hot tub, air conditioning, and free private parking.
Hilltown Cabin Hideaway: A River Runs Through It! - Massachusetts
10 121 reviews
Massachusetts
03/08 – 06/08
NZ$563/nighttotal: NZ$1689 (3 )

Hilltown Cabin Hideaway: A River Runs Through It!

1 2
cabin , Chesterfield
This three-bedroom lodge is situated in the Hilltowns of Western Massachusetts, approximately 16km from the William Cullen Bryant Homestead and the Rivulet Trail near Cummington.
The property, boasting a hot tub and bunkhouse, sleeps four guests and offers a fully equipped kitchen, Wi-Fi, and access to a 100-acre site bordering Bronson Brook, close to the Westfield River for swimming and fishing.
Mermaid House @ The Compound Beach Resort Habitat - Massachusetts
9.3 106 reviews
Massachusetts
07/08 – 11/08
NZ$2892/nighttotal: NZ$11568 (4 )

Mermaid House @ The Compound Beach Resort Habitat

2 2
apartment , Wareham
The Mermaid House @The Onset Beach Compound Resort - Habitat is a short walk from Onset Beach and Shell Point Beach in East Wareham, a peaceful area known for its relaxed atmosphere. This property has received excellent ratings for its location, cleanliness, and overall experience.
The house is spacious, with 102 square metres of space and the capacity to accommodate up to 8 guests. Amenities include a spa tub, a terrace, a garden, and parking, making it a perfect choice for families and groups looking for a comfortable and relaxing stay.
Cozy 2-bedroom Cabin With Ac. Fun For All Ages With Pond And Pool Access. - Massachusetts
Massachusetts
12/07 – 17/07
NZ$898/nighttotal: NZ$4490 (5 )

Cozy 2-bedroom Cabin With Ac. Fun For All Ages With Pond And Pool Access.

2 4
cabin , Falmouth
This lakeside lodge in East Falmouth offers a tranquil escape, situated a short drive from Cape Cod Beaches and Inkwell Beach, with the Woods Hole Ferry Terminal approximately 5 kilometres away.
This family-friendly cottage accommodates up to six guests with two bedrooms, a bathroom featuring a tub, and includes amenities such as air conditioning, Wi-Fi, a fridge, and microwave, alongside access to resort facilities including swimming pools and a hot tub.
©2026 cozycozy.com