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

Ideal North End 1brm Central To Everything - Massachusetts
9.6 177 reviews

Ideal North End 1brm Central To Everything

apartment, Boston
This one-bedroom flat is situated in the North End, a historic Italian neighbourhood in downtown Boston, within walking distance of TD Garden, Faneuil Hall, the harbour, and the aquarium. This property has consistently received excellent ratings for its location, cleanliness and overall guest experience.
The flat is modern and well-designed, with a comfortable layout and a floor area of 51 square metres. You'll find a fully equipped kitchen, a comfortable bedroom with a queen-size bed, a modern bathroom, and access to a range of amenities including Wi-Fi, air conditioning, and a washing machine.
74l - 2br Quincy - Cozy Couple Hideout Near Wollaston Beach - Massachusetts
9.7 3 reviews

74l - 2br Quincy - Cozy Couple Hideout Near Wollaston Beach

apartment, Quincy
This Quincy apartment, situated a short 6.4km drive from Boston's South Station and Back Bay, offers easy access to Wollaston Beach, a 10-minute walk away.
This two-bedroom, one-bathroom flat boasts a spacious 1100 square metre floor area, sleeps up to 18 guests, and includes a fully equipped kitchen, private parking, and a terrace with garden access.
Vineyard Haven Guest House - Sleeps 4, A/c, Walk To Town - Massachusetts
9.9 136 reviews

Vineyard Haven Guest House - Sleeps 4, A/c, Walk To Town

apartment, Tisbury
This family-friendly house is situated in Vineyard Haven, a short walk from the Vineyard Playhouse, Lake Tashmoo, and the ferry terminal. It has received excellent ratings for location, cleanliness, and overall user experience.
This two-bedroom house, spanning 107 square metres, comfortably accommodates up to four guests. The property offers a range of amenities, including a fully equipped kitchen, a terrace or balcony, a garden, a spa, a tennis court, and parking.
East Boston Apartment | 5 Min From Logan Airport - Massachusetts
9.8 34 reviews

East Boston Apartment | 5 Min From Logan Airport

apartment, Boston
This three-bedroom flat is located in East Boston's Eagle Hill district, offering proximity to a park just 200 metres away, Logan Airport within a five-minute journey, and Downtown Boston a ten-minute commute, with the MBTA Blue Line a ten-minute walk for city exploration.
This family-friendly residence accommodates up to ten guests, featuring air conditioning, a garden, and a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher, making it suitable for families and business travellers.

Top cities

Best pet friendly Massachusetts holiday rentals

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

Walk To Town From This Cozy Home All To Yourself - Massachusetts
9.9 22 reviews

Walk To Town From This Cozy Home All To Yourself

apartment, Northampton
This renovated 1890s farmhouse, a 10-minute walk (approx. 1.6km) from Northampton town centre, Smith College, and Northampton railway station (with direct trains to/from New York City), offers a pet-friendly apartment rental.
The two-bedroom, two-bathroom property sleeps five guests and includes a fully equipped kitchen with dishwasher, air conditioning, a jacuzzi, garden, parking, and EV charging; Google Home is also available.
Harmony Medical Suites Chinatown - Massachusetts
8.0 145 reviews

Harmony Medical Suites Chinatown

studio, Boston
This Boston flat is situated in Chinatown, offering convenient access to the city centre within 700 metres, a six-minute walk to Boston South Station and the Freedom Trail, and an eleven-minute walk to the Boston Tea Party Ship & Museum.
This apartment provides air-conditioned accommodation with complimentary WiFi, a kitchen equipped with a fridge, microwave, and dishwasher, and on-site fitness facilities, with parking also available.
3 Mi To Onset Beach & Village! Pet-friendly Apt - Massachusetts
10 2 reviews

3 Mi To Onset Beach & Village! Pet-friendly Apt

apartment, Wareham
This pet-friendly apartment in Wareham is conveniently located near Onset Beach and within 24-47km of Cape Cod attractions such as Heritage Museums & Gardens and Plimoth Patuxet Museums.
The 42 square metre self-catering flat offers one bedroom, one bathroom, and sleeps up to seven guests, boasting air conditioning, free Wi-Fi, parking, and a fully equipped kitchen including a fridge and microwave.
3 Mi To Onset Beach & Village! Pet-friendly Apt - Massachusetts
9.0 2 reviews

3 Mi To Onset Beach & Village! Pet-friendly Apt

apartment, Wareham
This Wareham apartment, ideally located near Onset Beach (4.8km), Swift's Beach (6.4km), and Myles Standish State Forest (12.9km), offers easy access to beaches and family attractions like Water Wizz (3.2km).
The 42-square-metre self-catering flat features one bedroom, one bathroom, sleeps four guests, and includes amenities such as a kitchenette with a fridge and microwave, air conditioning, parking, Wi-Fi, and two Smart TVs.

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

2br Condo In Cape Cod W/ Patio & Laundry - Massachusetts
No reviews

2br Condo In Cape Cod W/ Patio & Laundry

apartment, Mashpee
This Mashpee condo is conveniently located near Mashpee Commons (a short 1.8km walk), approximately 19km from Cape Cod beaches, and a 5km drive from the Cape Cod Children's Museum.
This two-bedroom, two-bathroom apartment sleeps six, offering on-site parking, a swimming pool, hot tub, and free Wi-Fi; nearby attractions include Inkwell Beach and the ports of Woods Hole and Hyannis.
New! Coastal Comfort With Stunning Harbor Views - Massachusetts
10 5 reviews

New! Coastal Comfort With Stunning Harbor Views

apartment, Plymouth
This coastal apartment in Plymouth offers direct harbour views, located 6.4 kilometres from Plymouth Rock and Plimoth Patuxet Museums, with private access to a beach just 152 metres away.
This 147 square metre flat accommodates up to six guests with three bedrooms and two bathrooms, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, and seasonal swimming pool access from Memorial Day to Labor Day.
Luxury Grand Oasis | Pool · Gym · Parking · 2br - Massachusetts
9.9 123 reviews

Luxury Grand Oasis | Pool · Gym · Parking · 2br

apartment, Everett
This Everett apartment, situated in the Commercial Triangle, offers easy access to Boston city centre via the Silver Line and Route 1.
The two-bedroom, one-bathroom flat sleeps six guests and boasts resort-style amenities including a swimming pool, fitness centre, and secure parking, plus modern kitchen and luxurious bedrooms with smart TVs.
Sleeps 15  Pool  Retreat - Massachusetts
10 38 reviews

Sleeps 15 Pool Retreat

apartment, Brimfield
Abigail's Nest, a spacious farmhouse-style property in Brimfield, Massachusetts, is located minutes from Sturbridge and the Brimfield Flea Market.
This 279-square-metre (2997 sq ft) holiday home boasts four bedrooms, three bathrooms, and can accommodate up to fifteen guests, featuring a large kitchen, swimming pool, terrace, garden, and parking.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts holiday rentals with parking

Riverfront Boston Retreat W/parking & Backyard! - Massachusetts
10 4 reviews

Riverfront Boston Retreat W/parking & Backyard!

apartment, Medford
This four-bedroom house in Medford offers a prime Mystic Riverfront location, providing direct access to walking trails and situated conveniently opposite the Medford Farmer's Market and Condon Shell, with downtown Boston just 15 minutes away and Tufts University less than 1 kilometre distant.
This family-friendly property accommodates up to nine guests with a fully equipped kitchen, air conditioning, a garden with a gas grill, and private off-street parking for three vehicles, ideal for those seeking a comfortable stay with easy access to local attractions and universities.
Escape To The Lake! - Massachusetts
10 67 reviews

Escape To The Lake!

apartment, Ashburnham
This lakefront house in Ashburnham, Massachusetts, offers stunning Sunset Lake views and is conveniently located near Wachusett Mountain (for skiing) and Mount Monadnock (for hiking), though precise distances aren't specified.
The three-bedroom, two-bathroom property sleeps five, boasts a fully equipped kitchen including a dishwasher, a jacuzzi, and access to two kayaks for exploring the lake, plus a garden and parking.
The Crows Nest - 1747 Historic Isaac Pierce House 2nd Floor Centrally Located - Massachusetts
9.8 210 reviews

The Crows Nest - 1747 Historic Isaac Pierce House 2nd Floor Centrally Located

apartment, Somerset
This two-bedroom flat is situated in a quiet historic neighbourhood on Main Street in Somerset, just a short distance from Bristol, Newport, Providence, and Boston. It has received excellent ratings for location, cleanliness, and overall user experience.
The 130 square metre flat can comfortably accommodate up to six guests and offers a range of amenities including high-speed internet, a fully equipped kitchen, a Jacuzzi, a garden, a spa, a tennis court, and parking.
Historic Huntington Home - Walk To Westfield River - Massachusetts
8.5 47 reviews

Historic Huntington Home - Walk To Westfield River

house, Huntington
This charming house is situated in Huntington, a short distance from the Westfield River and within easy reach of attractions like The Big E, Eastern States Expo Center, and Cranwell Spa & Golf Club. The property has received excellent ratings for its location, cleanliness, and overall experience.
The house offers three bedrooms and two bathrooms, accommodating up to six guests comfortably within its 279 square metres of floor space. Guests can enjoy a well-equipped kitchen, a private patio with river views, a garden, free Wi-Fi, and parking.
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