Compare villa rentals in Massachusetts from 100+ providers!

12003 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Massachusetts villas
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

12003 Villa rentals in Massachusetts

Best Massachusetts villas and beach houses with a pool

Among the 12003 accommodations in Massachusetts, here are the 4 best villas and beach houses with a pool

325 M² House ∙ 4 Bedrooms ∙ 8 Guests - Massachusetts
No reviews

325 M² House ∙ 4 Bedrooms ∙ 8 Guests

house, Plymouth
This oceanfront bluff home in Cape Cod, Plymouth, offers panoramic Atlantic views, situated 3.3 miles from Sagamore Beach and 3702 feet from Shaws Supermarket.
This 3490 sq ft house accommodates 8 guests with 4 bedrooms and 4 bathrooms, featuring a heated swimming pool, Jacuzzi, private beach access, a separate suite above the garage, and includes daily exclusive free tickets to local attractions through the Xplorie partnership.
Waterfront Cottage In Summer Village W/ Grill - Massachusetts
10 2 reviews

Waterfront Cottage In Summer Village W/ Grill

cottage, Westford
This charming cottage is located in the Summer Village district of Westford, just a short drive from Westford Town Common and Kimball Farm, offering easy access to local attractions and activities. It's perfect for families or groups looking for a comfortable and convenient getaway.
This 2-bedroom, 1-bathroom vacation rental comfortably accommodates up to 6 guests. It features a fully equipped kitchen, laundry facilities, air conditioning, a private fire pit, a shared pool, and a hot tub for relaxation.
Luxurious Villa With Pool And Gardens - Amazing Private Estate Retreat - Massachusetts
No reviews

Luxurious Villa With Pool And Gardens - Amazing Private Estate Retreat

house, Dedham
This spacious 8,000+ sq. ft. estate in Dedham's Precinct 1 residential area offers convenient access to major routes into Boston, with Legacy Place and Dedham Square a short drive away.
This family-friendly house features a seasonal outdoor swimming pool, beautifully maintained gardens, 8 bedrooms accommodating up to 20 guests, and a full-sized kitchen, ideal for extended stays and professionals.
Overlook Poolside Getaway With Seasonal Pool - Massachusetts
10 1 review

Overlook Poolside Getaway With Seasonal Pool

house, Falmouth
This Falmouth vacation home is located near South Cape Beach State Park (4.6 miles) and about 14 miles from attractions such as the Sandwich Glass Museum, Heritage Museums & Gardens, and Cape Cod Gateway Airport.
This 1840-square-foot property boasts one bedroom, two bathrooms, and accommodates up to 11 guests, featuring a private pool, a fully equipped kitchen with dishwasher, free Wi-Fi, in-house laundry, and a relaxing garden.

Top cities

Best family friendly Massachusetts villas and beach houses

Among the 12003 accommodations in Massachusetts, here are the 4 best family friendly villas and beach houses

Breezy Marie - Massachusetts
No reviews

Breezy Marie

house, Plymouth
House listing. You will be in Plymouth.
Facilities and services include a swimming pool, an iron and a barbecue. This is a family-friendly house!
Serene Lake Access And Hot Tub - Cozy Charming Escape - Massachusetts
No reviews

Serene Lake Access And Hot Tub - Cozy Charming Escape

house, Billerica
This modern lake house is located on Nutting Lake in Billerica, offering direct lake access and is approximately 40 miles from Boston and 40 miles from the New Hampshire Seacoast.
This family-friendly house sleeps 10 guests and features 4 bedrooms, 3 bathrooms, a private hot tub, a Pac-Man arcade machine, and a full kitchen with a fridge, freezer, microwave, and dishwasher.
Relax, Unwind & Enjoy Amazing Waterviews - Massachusetts
No reviews

Relax, Unwind & Enjoy Amazing Waterviews

house, Bourne
This Cape Cod cottage in Bourne offers stunning water views of Eel Pond with nearby ocean access via Monument Beach, and is located within 3.1 miles of Barlows Landing Beach and Hen's Cove Public Beach.
This family-friendly rental accommodates up to 4 guests with 2 bedrooms and 1 bathroom, featuring air conditioning, internet, a full kitchen, and includes the Xplorie program with $750 in daily free tickets to local attractions.
Private Sun Bedroom In Harvard House - Massachusetts
9.8 269 reviews

Private Sun Bedroom In Harvard House

apartment, Waltham
This family-friendly vacation home in Waltham is located on a river with serene views, within 3 miles of Bentley College and Boston Children's at Waltham. It has excellent user, location and cleanliness ratings.
The house has 5 bedrooms, a private balcony for outdoor relaxation, a cozy fireplace, a fully equipped kitchen with a refrigerator and oven, and free WiFi. Pets are allowed, it's family friendly, and there's parking.

Frequently Asked Questions about villa rentals in Massachusetts

  • What are the must-see attractions in Massachusetts?

    Massachusetts boasts a ton of iconic spots! For history buffs, there's Plymouth, the site of the Pilgrims' landing, and Boston, with its Freedom Trail showcasing revolutionary landmarks like Faneuil Hall and the Paul Revere House. Art lovers should head to the Museum of Fine Arts in Boston or the Norman Rockwell Museum in Stockbridge. And don't forget Salem, steeped in witch trial history and maritime charm.
  • What are the best villa rentals in Massachusetts?

  • Is Massachusetts known for mountains, beaches, forests, or other types of landscapes?

    Massachusetts offers a diverse range of landscapes. You'll find stunning beaches along Cape Cod and the North Shore, perfect for swimming and sunbathing. The Berkshires region in western Massachusetts features rolling hills and mountains, ideal for hiking and scenic drives. Plus, there are plenty of forests throughout the state, offering opportunities for camping and exploring the great outdoors. It's a really varied state geographically.
  • What are the best villa rentals with a pool in Massachusetts?

  • What are some unique ways to learn about the culture of Massachusetts by engaging with its people?

    One great way is to attend a local farmers market; many towns host them regularly, showcasing regional produce and crafts. Visiting a historical reenactment, like those held at Plimoth Patuxet Museums, provides a hands-on experience. Also, consider taking a food tour in Boston or a walking tour in a smaller town – you'll meet locals and learn about their lives and traditions.
  • What are the best villa rentals with a jacuzzi in Massachusetts?

  • How much time should you set aside to thoroughly explore Massachusetts?

    A week allows you to see the highlights, but to truly experience Massachusetts, you'd need at least two weeks. The state is diverse, with Boston, Cape Cod, the Berkshires, and many other regions, each requiring time to explore properly. A longer trip lets you delve deeper into the state's history, culture, and natural beauty.
  • What are the best villa rentals for families and kids in Massachusetts?

  • Is there anything you might not think to pack for a trip to Massachusetts?

    Depending on the time of year, pack layers! Massachusetts weather can be unpredictable. Even in summer, evenings can be cool. Also, comfortable walking shoes are a must, as exploring many of the historical sites and charming towns involves a lot of walking. And don't forget insect repellent, especially if you plan on hiking or spending time outdoors.
  • What are the best pet friendly villa rentals in Massachusetts?

  • What cultural experiences or workshops in Massachusetts offer something different?

    Consider a whale watching tour from Provincetown or Gloucester – it's a unique way to experience the maritime culture. Many museums offer specialized workshops, such as pottery classes or historical reenactment participation. Alternatively, check out the many local theater productions across the state, showcasing both established and emerging talent.
  • What are the best villa rentals with parking in Massachusetts?

  • Are there any food festivals in Massachusetts where you can try local food?

    The Topsfield Fair is a large agricultural fair with plenty of local food options. Many towns and cities host smaller, seasonal festivals throughout the year, often featuring local cuisine. Check local event listings for specific dates and locations.
  • What seasonal natural events, such as migrations or blooming periods, occur in Massachusetts?

    In spring, witness the vibrant blooms of wildflowers across the state, particularly in the Berkshires. Fall brings spectacular foliage, with the leaves changing color across the landscape. Bird migration is also significant, with various species passing through during spring and fall.
  • What exclusive experiences are available when visiting Massachusetts?

    Consider a private tour of a historic home, such as the Adams National Historical Park or the Longfellow House. A private sailing charter on Cape Cod or the islands offers a luxurious and unique perspective. For a truly exclusive experience, book a stay at a luxury resort in the Berkshires or on Martha's Vineyard.

Nearby regions

Best Massachusetts houses with a kitchen

Enjoy Boston Private Patio On Montgomery Park - Massachusetts
8.5 2 reviews

Enjoy Boston Private Patio On Montgomery Park

house, Boston
This Back Bay home is a short walk from the Hynes Convention Center and a mile from the Boston Public Garden, offering easy access to major attractions.
The 1190-square-foot house features two bedrooms, one bathroom, and accommodates five guests, complete with a fully equipped kitchen, in-unit laundry, air conditioning, and a private patio.
Waterfront Cabin On Long Pond - Massachusetts
9.7 76 reviews

Waterfront Cabin On Long Pond

cabin, Plymouth
Dick's Cabin is a secluded waterfront cottage located in Cornish Point, a quiet wooded area about an hour from Boston and less than 4 miles from the nearest grocery store. The cabin has received excellent ratings for its location, cleanliness, and overall experience.
This cozy one-bedroom cabin can accommodate up to two guests. It includes a kitchen with a fridge and microwave, a garden, parking, and internet access. Guests can enjoy swimming, canoeing, and stunning lake views from the screened porch, as well as access to shared amenities like a dock, grill, and picnic table.
Cozy Oasis Near South End - Massachusetts
No reviews

Cozy Oasis Near South End

house, Boston
This Boston vacation home is located near the South End, offering convenient access to the Museum of Fine Arts (1.1 miles), MIT (2.8 miles), and Boston University (2.9 miles).
This spacious 4,000 square foot house accommodates up to 17 guests across 5 bedrooms, featuring a fully equipped kitchen with a dishwasher and oven, air conditioning, 3 bathrooms, and private parking.
Walk To Swift's Beach! Classic Cottage W/ Deck - Massachusetts
10 5 reviews

Walk To Swift's Beach! Classic Cottage W/ Deck

house, Wareham
Wareham Cottage, a two-bedroom house near Swift Beach, offers easy access to attractions like Heritage Museums & Gardens (within 17-21 miles).
This 670-square-foot vacation rental features a fully equipped kitchen, air conditioning, a private garden, spa, parking, and free Wi-Fi, comfortably accommodating families or small groups.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts villas and beach houses with jacuzzi

Ocean's Edge With Pool, Hot Tub & Beach Access - Massachusetts
No reviews

Ocean's Edge With Pool, Hot Tub & Beach Access

house, Plymouth
This oceanfront bluff vacation home in Plymouth offers panoramic Atlantic views, private beach access, and is located 3.3 miles from Sagamore Beach and 6.6 miles from the Cape Cod Canal.
This family-friendly rental accommodates up to 8 guests with 4 bedrooms and 4 bathrooms, featuring a heated pool, spa, Jacuzzi, game room, and includes $750 in daily Xplorie tickets for local attractions.
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 house offers a Lakeview retreat directly across from Nutting Lake, a 15-block walk to Billerica Center's restaurants and shops, and a 5-minute drive to the Billerica Purple Line Commuter Rail.
This family-friendly home accommodates up to 8 guests with 3 bedrooms, 2 bathrooms, a modern kitchen with stainless steel appliances, a private hot tub, a BBQ grill, and fast Wi-Fi.
Winery Farmhouse W/ Private Hot Tub & Wine Tasting - Massachusetts
9.9 128 reviews

Winery Farmhouse W/ Private Hot Tub & Wine Tasting

gîte, North Andover
The Ice House apartment is situated on a 5-acre Marble Ridge Farm estate in North Andover, a short drive from hiking trails, beaches, and the Harold Parker State Forest. This property has earned excellent ratings for location, cleanliness, and overall experience.
The apartment has three bedrooms and one bathroom, comfortably accommodating up to seven guests. Guests enjoy access to a swimming pool, garden, and a patio with lounge chairs, tables, and umbrellas, as well as complimentary farm vineyard tours and wine tastings.
Lakeview Getaway With Hot Tub - Massachusetts
No reviews

Lakeview Getaway With Hot Tub

house, Billerica
This Billerica vacation home is located an 8-minute walk from Micozzi Beach, 10 miles from Minute Man National Historical Park, and 15 miles from the Brattle Theatre.
This 1400-square-foot property boasts three bedrooms, two bathrooms, and can comfortably accommodate up to 15 guests, featuring a fully equipped kitchen, Jacuzzi, private parking, and outdoor play areas.
©2026 cozycozy.com