Holiday Rentals in Massachusetts

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Massachusetts holiday rentals
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Massachusetts holiday rentals: compare the best deals

Best family friendly Massachusetts holiday rentals

Among the 61432 accommodations in Massachusetts, here are the 4 best family friendly rentals

Indulge In The Ultimate Vacation Experience At This Exquisite Custom Log Home. - Massachusetts
10 32 reviews

Indulge In The Ultimate Vacation Experience At This Exquisite Custom Log Home.

apartment, Oak Bluffs
This Oak Bluffs seaside property is situated a short walk (under 1.6km) from Eastville Beach and Martha's Vineyard Hospital, and less than 1.6km from Oak Bluffs Harbour and the public library.
This 242 square metre house offers four bedrooms, three bathrooms, sleeps eight guests, and boasts a jacuzzi, terrace, garden, parking, and free Wi-Fi, ideal for families seeking a relaxing beach holiday.
Home Away From Home - Massachusetts
9.0 1 review

Home Away From Home

house, Leicester
This Leicester house, near the DCU Center Arena & Convention Centre (16km), Fitton Football Stadium (14.8km), and Worcester Regional Airport (11km), offers excellent location ratings.
Sleeping up to 19 guests, this 14 square metre property boasts 5 bedrooms, 4 bathrooms, 2 living rooms, a fully equipped kitchen, garden, terrace, parking, and free Wi-Fi; laundry service is also provided.
Massachusetts Vacation Rental: 5 Mi To Fall River - Massachusetts
9.0 14 reviews

Massachusetts Vacation Rental: 5 Mi To Fall River

apartment, Somerset
This Somerset beach house, located within 10km of Hartley's Pork Pies, Pierce Beach & Playground, Somerset Marina, the Marine Museum at Fall River, and the USS Massachusetts, offers a convenient base for exploring the area.
This three-bedroom, one-bathroom property boasts 107 square metres of floor space, sleeps six guests, includes a fully equipped kitchen, air conditioning, parking, internet access, and a fireplace, perfect for a family holiday.
Big Farmhouse In The Foothills Of The Berkshires - Massachusetts
10 148 reviews

Big Farmhouse In The Foothills Of The Berkshires

apartment, Russell
This pet-friendly house in Russell, Massachusetts, is situated within 9.6km of the Westfield River, Tekoa Park, and Westfield State University.
This 149 square metre property sleeps eight guests and boasts three bedrooms, two bathrooms, a fully equipped kitchen with fridge and microwave, a private garden with barbecue, patio, and a DVD player; enjoy outdoor relaxation and cookouts.

Top cities

Best pet friendly Massachusetts holiday rentals

Among the 61432 accommodations in Massachusetts, here are the 4 best pet friendly rentals

Blueground | East Cambridge, Fitness Center, Nr Charles River - Massachusetts
No reviews

Blueground | East Cambridge, Fitness Center, Nr Charles River

apartment, Cambridge
This modern, fully equipped one-bedroom flat is situated in East Cambridge, a district close to the Massachusetts Institute of Technology (MIT) and Kendall Square, with straightforward access to central Boston via the T.
Offering 69 square meters of living space for up to two guests, this apartment includes a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, on-site laundry facilities, and parking, with pets welcome subject to conditions.
Lakefront Retreat & Yard Oasis - Massachusetts
10 2 reviews

Lakefront Retreat & Yard Oasis

apartment, Plymouth
This lakeside Plymouth, Massachusetts flat, situated directly opposite White Island Pond and minutes from Plymouth's town centre, offers direct waterfront access.
The two-bedroom, two-bathroom property sleeps eight, boasting a fully renovated interior with two living areas, a basement games room with ping-pong, a private backyard with pergola, gas grill and fire pit, plus an attached garage and complimentary kayaks.
2 Family Home - Massachusetts
No reviews

2 Family Home

apartment, Brockton
This one-bedroom flat in Brockton offers a peaceful base in a residential area, conveniently situated near the main street, a shopping centre, and essential amenities, with Gillette Stadium and Xfinity Center approximately 10 kilometres away.
This pet-friendly accommodation provides a private garden and patio, air conditioning, and Wi-Fi, accommodating up to two guests and ideal for exploring local attractions like Campanelli Stadium and Sky Zone Boston Indoor Trampoline Park.
Luxury Home  Private Yard  15 Min To Gillette! - Massachusetts
10 5 reviews

Luxury Home Private Yard 15 Min To Gillette!

apartment, Attleboro
This newly constructed private residence in Attleborough offers a secluded and comfortable stay, situated less than 24 kilometres from Gillette Stadium, making it ideal for attending the 2026 FIFA World Cup matches.
This pet-friendly flat boasts a full kitchen and BBQ grill, with a spacious outdoor deck and large garden perfect for tailgating and relaxation, providing free on-property parking and self check-in for up to six guests.

Frequently asked questions about holiday rentals in Massachusetts

  • What are the must-see sights in Massachusetts?

    For must-see sights in Massachusetts, you've got plenty of options! Boston's Freedom Trail is a classic, taking you past historical landmarks like the Paul Revere House and Boston Common. Then there's Plymouth, where you can explore Plimoth Patuxet Museums and learn about the Pilgrims. For art and culture, the Museum of Fine Arts in Boston is world-renowned, and Salem offers a fascinating glimpse into the city's witch trial history. Don't forget the beautiful beaches on Cape Cod, like those in Chatham or Provincetown.
  • What are the best Airbnb and vacation rentals in Massachusetts?

    Near Boston Historic Two-bedroom With Modern Amenities, Steps To The Green Line & Minutes From Boston #15 and Luxurious Renovated House are the most popular Airbnb and vacation rentals in Massachusetts among travelers.

  • Are there unique natural phenomena in Massachusetts?

    Massachusetts boasts some lovely natural features. The Berkshires offer stunning mountain scenery, perfect for hiking. The coastline is dramatic, with places like the dramatic cliffs of Race Point Beach on Cape Cod. You can also explore the diverse ecosystems of the many state parks and forests, like the Mount Greylock State Reservation, home to the highest point in Massachusetts.
  • What are the most popular Airbnbs in Massachusetts?

  • What essentials should you bring along for a trip to Massachusetts?

    Pack for all types of weather! Massachusetts experiences varied conditions. Comfortable walking shoes are a must, especially if you plan on exploring Boston or hiking. Layers of clothing are recommended, as temperatures can change quickly. Don't forget sunscreen, a hat, and sunglasses, even on cloudy days. A reusable water bottle is also essential, especially during warmer months.
  • What are the best vacation rentals with a pool in Massachusetts?

  • What famous events or festivals are happening in Massachusetts?

    The Boston Marathon is a world-famous event held annually in April. Many smaller, local festivals take place throughout the year, celebrating everything from food to music. Check local listings for specific dates and events during your visit. The Fourth of July celebrations in many towns are also quite spectacular.
  • What are the best rentals for families and kids in Massachusetts?

  • Where can you find the best restaurants serving local dishes in Massachusetts, and what are the must-try specialties?

    For delicious local food, explore the North End in Boston for authentic Italian cuisine. You can find classic New England clam chowder and lobster rolls throughout the state. Many restaurants feature fresh seafood, given the state's coastal location. Trying a 'Boston cream pie' is a must for dessert lovers.
  • What are the best rentals or Airbnbs with a jacuzzi in Massachusetts?

  • What are some less-famous attractions in Massachusetts that are worth a visit?

    Consider visiting the charming town of Lenox in the Berkshires, known for its beautiful scenery and cultural attractions like Tanglewood. The Arnold Arboretum in Boston offers a peaceful escape, showcasing diverse plant collections. The Plimoth Patuxet Museums, while well-known for the Pilgrims, is a great place to experience living history. Also, explore the many lighthouses along the coast.
  • What are the best activities for engaging with locals and understanding their culture in Massachusetts?

    Visiting local farmers' markets is a great way to interact with locals and sample regional produce. Attending a local sporting event, like a Red Sox game, provides a taste of the city's passion. Exploring smaller towns outside of Boston gives you a chance to meet people and experience a slower pace of life. Many towns hold festivals and events that are perfect for cultural immersion.
  • What unique natural landscapes and terrain features can travellers explore in Massachusetts?

    Massachusetts offers a diverse range of landscapes. The sandy beaches of Cape Cod contrast sharply with the rocky coastline of the North Shore. The rolling hills of the Berkshires provide opportunities for hiking and scenic drives. The state also has numerous forests, wetlands, and ponds, offering diverse wildlife viewing opportunities. Don't forget the islands, like Martha's Vineyard and Nantucket.
  • How many days are ideal for a trip to Massachusetts, and what are some itinerary suggestions?

    A week is a good amount of time to explore Massachusetts, allowing you to see the main attractions in Boston and venture outside the city. A shorter trip of 3-4 days could focus on Boston and its surrounding areas. A possible itinerary could include 2 days in Boston, 1 day in Salem, and 2 days exploring Cape Cod or the Berkshires.

Nearby regions

Best Massachusetts holiday rentals with a pool

Among the 61432 accommodations in Massachusetts, here are the 4 best rentals with a pool

Whole House Steps From Pleasant Pond - Massachusetts
9.4 57 reviews

Whole House Steps From Pleasant Pond

apartment, Wenham
This charming house is located in Wenham, just a short drive from the Wenham Museum and other local attractions, making it a great base for exploring the area. The property has received excellent reviews from previous guests, highlighting its comfort and convenience.
The house has one bedroom and two bathrooms, comfortably accommodating up to four guests. It offers a range of amenities, including a swimming pool, terrace, garden, and parking, as well as modern kitchen appliances, laundry facilities, and internet access.
Beach, Pool, Deck, And Views - New Seabury - Massachusetts
10 5 reviews

Beach, Pool, Deck, And Views - New Seabury

apartment, Mashpee
This New Seabury townhome, situated in the Mews on the Knoll neighbourhood, enjoys a prime location overlooking the 8th tee and green of the Dunes Golf Course and is a kilometre walk from Nantucket Sound beach.
The two-bedroom, two-bathroom property sleeps six, boasting a fully equipped kitchen with stainless steel appliances, a private swimming pool, and child-friendly amenities including a highchair and playpen; nearby attractions include Mashpee Commons and the Mashpee National Wildlife Refuge.
Modern Cape Cod Home In Vibrant Beach Community - Steps To Beach; Pool Access!! - Massachusetts
10 22 reviews

Modern Cape Cod Home In Vibrant Beach Community - Steps To Beach; Pool Access!!

apartment, Falmouth
This East Falmouth holiday home is situated near the sea, within 3.2km of Cape Cod Beaches and the Waquoit Bay National Estuarine Research Reserve, and within 9.7km of the Cape Cod Children's Museum and Mashpee River Reservation.
This spacious four-bedroom property, boasting 223 square metres of floor area, comfortably sleeps ten guests and includes a swimming pool, terrace, garden, free Wi-Fi, and a fully equipped kitchen with dishwasher.
Blueground | South End, Pool, Nr Boston Common - Massachusetts
No reviews

Blueground | South End, Pool, Nr Boston Common

apartment, Boston
This Boston flat is located in the South End, offering convenient access to Newbury Street, Faneuil Hall Marketplace, Boston Common, Boston Harbour, TD Garden, and Fenway Park.
This 72 square metre apartment sleeps two guests and features a modern kitchen, air conditioning, and building amenities including a swimming pool and sauna, with on-site parking available for a fee.

Best Massachusetts holiday rentals with parking

2 Bedroom Pet-friendly Apt Steps To The Beach - Massachusetts
9.6 206 reviews

2 Bedroom Pet-friendly Apt Steps To The Beach

apartment, Salisbury
This family-friendly apartment is located in Salisbury, a short distance from the beautiful beaches of Salisbury Beach State Reservation, Salisbury Beach, and Seabrook Beach. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment has two bedrooms, a bathroom, and a living area, providing ample space for up to six guests. It also offers a range of amenities including a fully equipped kitchen, air conditioning, a swimming pool, and a terrace, ensuring a comfortable and enjoyable stay.
Cozy Boston Getaway Apartment Perfect For 2026 World Cup Visit, Free Parking - Massachusetts
9.4 67 reviews

Cozy Boston Getaway Apartment Perfect For 2026 World Cup Visit, Free Parking

apartment, Boston
This one-bedroom apartment is situated in a peaceful neighbourhood in Boston, just 11km from the Hynes Convention Center and Back Bay, and 10km from the Boston Museum of Fine Arts. It has received excellent ratings for cleanliness and user experience, as well as a very good location rating.
The apartment offers 56 square metres of space, accommodating up to 5 guests. It features a fully equipped kitchen, air conditioning, a private garden, and free private parking, making it an ideal choice for families or groups of friends exploring Boston.
Vintage 5br Apt In Boston With Free Parking - Massachusetts
9.7 3 reviews

Vintage 5br Apt In Boston With Free Parking

apartment, Boston
This spacious 5-bedroom flat in Boston offers convenient access to Harvard University and Harvard Square, located approximately 4 kilometres away, with Brattle Theatre and Central Square Theatre also within 4 kilometres.
This substantial property boasts 167 square metres of living space, accommodating up to 22 guests with its five bedrooms and two bathrooms, and includes private parking and a balcony.
39 - 3br Quincy - Stunning Townhouse Near Adams - Massachusetts
9.7 241 reviews

39 - 3br Quincy - Stunning Townhouse Near Adams

apartment, Quincy
This newly built townhouse is located in Quincy, just 15 kilometres from Boston South Station and Back Bay, and 11 kilometres from the JFK Presidential Library & Museum. The apartment has received excellent ratings for location, cleanliness and user experience.
This three-bedroom apartment offers 177 square metres of space and can comfortably accommodate up to 13 guests. The apartment includes modern amenities such as a fully equipped kitchen with a dishwasher, air conditioning, free parking, and Wi-Fi.
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