Holiday Rentals in Massachusetts

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Massachusetts holiday rentals
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Best Holiday rentals and Airbnb offers in Massachusetts

Best family friendly Massachusetts holiday rentals

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

Bungalow 19 By The Little Alum Lake In Brimfield - Massachusetts
10 13 reviews

Bungalow 19 By The Little Alum Lake In Brimfield

apartment, Brimfield
This Brimfield detached house offers easy access to local attractions, located a 6-minute drive from St. Anne's Shrine and a 5-minute drive from Streeter Beach, with Heins Farm Conservation Area and Leadmine Mountain Conservation Area nearby.
This two-bedroom bungalow accommodates up to four guests and features a fully equipped kitchen, air conditioning, complimentary Wi-Fi, a private garden, and on-site laundry facilities, ideal for family holidays.
Charming Garden Level 1 Bedroom 1 Bath Apartment In Brockton - Massachusetts
8.0 15 reviews

Charming Garden Level 1 Bedroom 1 Bath Apartment In Brockton

apartment, Brockton
This Brockton flat is conveniently located approximately 4km from Signature Healthcare, 5.3km from Massasoit Community College, and 5km from Brockton Mall.
The one-bedroom apartment, sleeping up to three guests, features a kitchen with fridge and microwave, air conditioning, parking, Wi-Fi, and is close to recreational areas such as Blue Hills Reservation.
Home-like 4br-3ba Apt | Near Ashmont Station (New) - Massachusetts
10 24 reviews

Home-like 4br-3ba Apt | Near Ashmont Station (New)

apartment, Boston
This Dorchester apartment, a 7-10 minute walk from Ashmont Red Line station, offers easy access to Boston city centre and is situated approximately 0.8 km from Highway 93.
Sleeping up to 12 guests comfortably in four bedrooms and with three bathrooms, this family-friendly property features a modern open-plan kitchen, living and dining area, private garden, parking, and high-speed internet access.
Beach Access|ac|free Parking|new Listing Discount - Massachusetts
9.8 64 reviews

Beach Access|ac|free Parking|new Listing Discount

house, Salisbury
This beachfront property in Salisbury, Massachusetts offers direct beach access and is within walking distance of Salisbury Beach State Reservation.
The two-bedroom condo sleeps six, features a fully equipped kitchen including fridge, freezer and microwave, high-speed WiFi, a Smart TV, air conditioning, and a shared outdoor dining area with grill; nearby attractions include mini-golf, arcades, and various restaurants.

Top cities

Best pet friendly Massachusetts holiday rentals

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

Keyless Entry Laundry In Bldg Pet Friendly - Massachusetts
8.8 4 reviews

Keyless Entry Laundry In Bldg Pet Friendly

apartment, Boston
This city centre flat in Boston offers prime access to public transport, being a 5-minute walk from Boston South Station and within 600 metres of the Freedom Trail, with the Boston Tea Party Ship & Museum a 9-minute walk away.
This pet-friendly one-bedroom flat, covering 120 square metres, accommodates up to three guests and features air conditioning, a fully equipped kitchen with a dishwasher, and on-site laundry facilities.
Polished South End Studio - Massachusetts
10 3 reviews

Polished South End Studio

apartment, Boston
This studio flat is situated in Boston's South End, a prime location offering convenient walking access to its well-regarded restaurants, independent shops, and local parks, with the nearest park being approximately 350 metres away.
This property allows pets, features air conditioning, a kitchenette equipped with a fridge and freezer, and accommodates two guests with a queen-size bed, all supported by a 24/7 guest messaging team.
Grand 3br Boston Home - Pet-friendly - Franklin Park & Red Line 558-1 - Massachusetts
9.5 9 reviews

Grand 3br Boston Home - Pet-friendly - Franklin Park & Red Line 558-1

apartment, Boston
This three-bedroom apartment in Boston is situated approximately 5.6 to 8 kilometres from attractions such as the Boston Aquarium, the John F. Kennedy Presidential Library and Museum, and Fenway Park.
The 75-square-metre property offers free Wi-Fi, private parking, a fully equipped kitchen including a dishwasher, two bathrooms, and accommodates up to 25 guests, making it ideal for families or large groups visiting Boston.
Centrally Located Back Bay 1 Bedroom - Massachusetts
9.0 3 reviews

Centrally Located Back Bay 1 Bedroom

apartment, Boston
This centrally located one-bedroom flat in Boston's Back Bay district is a short walk to Back Bay and Hynes Convention Centre, and within 1.6 kilometres of the Prudential Tower and Boston Museum of Fine Arts.
This 65 square metre apartment accommodates up to three guests with one bedroom and one bathroom, featuring air conditioning, free WiFi, and a kitchen equipped with a fridge and microwave oven, with pets welcome.

Frequently asked questions about holiday rentals in Massachusetts

  • What are the must-see sights in Massachusetts, United States?

    Massachusetts boasts a wealth of historical and cultural attractions. For history buffs, a trip to Boston is essential, including a visit to the Freedom Trail, Faneuil Hall, and the Boston Tea Party Ships & Museum. Plymouth, the site of the Pilgrims' landing, offers a glimpse into early American history. Salem's maritime history and connection to the Salem Witch Trials are also captivating. Beyond Boston, the charming coastal towns of Cape Cod and the Berkshires offer stunning scenery and quaint villages.
  • What are the best Airbnb and holiday rentals in Massachusetts?

    Near Boston Historic Two-bedroom With Modern Amenities, Luxurious Renovated House and Your Home For The Holidays are the most popular Airbnb and holiday rentals in Massachusetts among travellers.

  • Are there any unique natural phenomena in Massachusetts, United States?

    While Massachusetts doesn't have dramatic geological features like geysers, its coastline is remarkably diverse. The dramatic cliffs of the North Shore, the sandy beaches of Cape Cod, and the rocky shores of the islands offer unique coastal experiences. The Berkshires offer stunning mountain scenery and opportunities for hiking and exploring forests. The state's numerous ponds and lakes, like Walden Pond, are also noteworthy.
  • What are the most popular Airbnbs in Massachusetts?

  • What essentials should you bring to Massachusetts, United States?

    Packing for Massachusetts depends on the season. Comfortable walking shoes are a must, as exploring many of the historical sites and towns involves a lot of walking. Layers are recommended as the weather can be unpredictable, particularly near the coast. In the colder months, pack warm clothes, including a hat, gloves, and scarf. Sunscreen and insect repellent are also advisable, regardless of the season.
  • What are the best holiday rentals with a pool in Massachusetts?

  • What famous events or festivals are happening in Massachusetts, United States?

    The Boston Marathon, held annually in April, is a world-famous event. The Head of the Charles Regatta, a major rowing competition, takes place in October. Numerous smaller festivals and events occur throughout the year, celebrating everything from local produce to music and arts. Specific dates vary each year, so it is best to check local event listings closer to your travel dates.
  • What are the best rentals for families and kids in Massachusetts?

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

    The North End in Boston is renowned for its Italian-American cuisine. Try classic dishes like clam chowder, lobster rolls, and Boston cream pie. Many restaurants throughout the state offer fresh seafood, reflecting Massachusetts' coastal location. Farm-to-table restaurants in the Berkshires showcase regional produce. Exploring local farmers' markets is a great way to discover regional specialties.
  • What are the best rentals or Airbnbs with a jacuzzi in Massachusetts?

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

    The Plimoth Patuxet Museums offer a more immersive experience of 17th-century life than Plymouth Rock alone. The Mount Greylock State Reservation, the highest point in Massachusetts, provides stunning views. The charming town of Lenox in the Berkshires offers a tranquil escape. The many lighthouses along the coast, such as the Race Point Lighthouse on Cape Cod, provide picturesque settings and historical insights.
  • What are the best activities for engaging with locals and understanding their culture in Massachusetts, United States?

    Visiting local farmers' markets allows interaction with producers and a taste of regional produce. Attending local events and festivals provides opportunities to experience the community spirit. Exploring smaller towns and villages away from major tourist hotspots allows for a more authentic interaction with residents. Striking up conversations in local pubs and cafes can lead to interesting encounters.
  • What unique natural landscapes and terrain features can travellers explore in Massachusetts, United States?

    Massachusetts offers a diverse range of landscapes. The dramatic coastline, with its cliffs, beaches, and islands, is a key feature. The rolling hills and mountains of the Berkshires provide opportunities for hiking and scenic drives. The state's many ponds and lakes offer opportunities for swimming, boating, and fishing. The diverse forests provide habitats for a wide range of flora and fauna.
  • How many days are ideal for visiting Massachusetts, United States, and what are some itinerary suggestions?

    Seven to ten days allows for a good exploration of the state's highlights. A possible itinerary could include three days in Boston, two days exploring Cape Cod, and two days in the Berkshires. Alternatively, focus on a specific region for a deeper experience. A shorter trip could focus solely on Boston and its surrounding areas.

Nearby regions

Best Massachusetts holiday rentals with a pool

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

Clear Pond Getaway - Massachusetts
9.3 170 reviews

Clear Pond Getaway

apartment, Plymouth
Clear Pond Getaway is a beachfront flat located in Plymouth, just 6.1 miles from Plimoth Plantation and 22 miles from Heritage Museums & Gardens, making it a great base for exploring the area. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience.
This self-catering property features a fully equipped kitchen, a private terrace, and access to a swimming pool and garden. Guests can enjoy a range of activities on-site, including snorkeling, cycling, and fishing, as well as relax by the outdoor fireplace.
Beachfront W/ Hot Tub, Sauna, Pool, Fire Pits, Grill & Panoramic Views - Massachusetts
10 218 reviews

Beachfront W/ Hot Tub, Sauna, Pool, Fire Pits, Grill & Panoramic Views

apartment, Somerset
This waterfront apartment is located on a quiet dead-end road at the tip of Somerset, just 2 kilometres from Brayton Point Beach and offering stunning views of the Braga and Mount Hope Bridges. The property has received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The apartment features four bedrooms, two bathrooms, and can comfortably accommodate up to eight guests. Enjoy a range of amenities including a private sauna, a fully equipped kitchen, a fitness centre, a garden, and a private chef service, perfect for a relaxing and enjoyable stay.
Remodeled Cottage Retreat On The Lake, Close To Boston But Nestled In The Woods - Massachusetts
10 1 review

Remodeled Cottage Retreat On The Lake, Close To Boston But Nestled In The Woods

cottage, Groton
This Groton, Massachusetts lakeside property, situated on Lost Lake and approximately 72 kilometres from Boston, offers private beach access and proximity to the Westford Museum and the MIT Haystack Observatory.
The two-bedroom, one-bathroom holiday home sleeps six, boasting a fully equipped kitchen, lake views, a deck with barbecue, fire pit, and rentable canoe, plus beach chairs and life vests for family enjoyment.
Lake Access & Pools: Sun-soaked Westford Cottage! - Massachusetts
10 1 review

Lake Access & Pools: Sun-soaked Westford Cottage!

cottage, Westford
This Westford holiday home is located in the Summer Village district, offering convenient access to nearby beaches and is within driving distance of Lowell Heritage State Park and Great Brook Farm State Park.
The 74-square-metre property boasts two bedrooms, two bathrooms, sleeps four guests, and includes a fully equipped kitchen, swimming pool, Jacuzzi, and garden, plus on-site hot tub and games room.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts holiday rentals with parking

Historic Old Town Retreat Walk To Harbor - Massachusetts
9.8 130 reviews

Historic Old Town Retreat Walk To Harbor

apartment, Marblehead
This apartment is situated in the heart of Marblehead, within a 10-minute walk of Gas House Beach, Fort Sewall, and King Hooper Mansion, offering easy access to the town's key attractions. The apartment has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
This one-bedroom flat, spanning 84 square metres, comfortably accommodates two guests. Amenities include a well-equipped kitchen with a fridge, freezer, microwave, and dishwasher, as well as air conditioning, a garden, and parking.
Downtown Falmouth 1 Bedroom Apartment - Massachusetts
7.8 6 reviews

Downtown Falmouth 1 Bedroom Apartment

apartment, Falmouth
This Falmouth flat is conveniently located near Main Street and Mashpee Commons, offering easy access to the Woods Hole Ferry Terminal and other attractions.
The one-bedroom apartment sleeps three, featuring a queen bed and sofa bed, plus free Wi-Fi, heating, and an iron; nearby are the Cape Cod Children's Museum and Mashpee River Reservation.
Unique & Peaceful Boston Home, Ideal For 2026 World Cup Visitor, Free Parking - Massachusetts
9.2 91 reviews

Unique & Peaceful Boston Home, Ideal For 2026 World Cup Visitor, Free Parking

apartment, Boston
This apartment is located in a tranquil neighbourhood in Boston, just 10km from the Boston Museum of Fine Arts and 11km from Fenway Park. It has consistently received excellent ratings for its cleanliness, location and overall experience.
The apartment is a spacious two-bedroom property with one bathroom, covering 88 square metres and comfortably accommodating up to five guests. It offers a range of amenities including a fully equipped kitchen, private garden, free parking, and a washing machine, making it ideal for families or groups of friends exploring Boston.
Main Street Suite - Massachusetts
9.9 155 reviews

Main Street Suite

apartment, Sturbridge
This Sturbridge suite enjoys a convenient location next to a craft beer pub and opposite a Japanese restaurant, offering easy access to Old Sturbridge Village and other local attractions.
The self-contained apartment features a queen-size bed, a coffee bar with a Keurig machine and microwave, and accommodates two guests in its open-plan layout with a private porch.
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