Vacation Rentals in Massachusetts

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Massachusetts holiday rentals
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61432 Holiday rentals and Airbnb in Massachusetts

Best family friendly Massachusetts holiday rentals

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

Modern Luxury Home With Fireplace & Game-room - Massachusetts
9.2 11 reviews

Modern Luxury Home With Fireplace & Game-room

apartment, Brockton
This three-bedroom apartment is located in Brockton, just 37 kilometres from Fenway Park and Boston South Station, offering easy access to the city's attractions. The apartment has received very good ratings for cleanliness and user experience, and the location is rated as good.
The apartment can comfortably accommodate up to eight guests and features a fully equipped kitchen, a modern design with a fireplace and a games room, as well as free private parking. Guests can enjoy a relaxing atmosphere with a flat-screen TV, and the apartment is conveniently located near a Topgolf facility for entertainment.
Historic Harvard & Mit Victorian - Massachusetts
9.0 236 reviews

Historic Harvard & Mit Victorian

apartment, Cambridge
This Victorian flat is ideally located in Cambridge, close to both Harvard and MIT, and within easy walking distance of John F. Kennedy Park, Harvard Square, and the Brattle Theatre. The property has consistently received excellent ratings for its cleanliness, location and overall experience.
The flat offers two bedrooms, providing comfortable accommodation for couples or small families. You'll also find a living room, a fully equipped kitchen with a dishwasher, and a garden where you can relax and enjoy the fresh air. The property also boasts a spa bath, free Wi-Fi, and parking, making it a great choice for those looking for a comfortable and convenient stay in Cambridge.
Newly Renovated Condo 1 Mile From Salem - Massachusetts
No reviews

Newly Renovated Condo 1 Mile From Salem

apartment, Beverly
This newly renovated flat in Beverly is located 1.6 kilometres from Salem, a short 18-minute walk to Dane Street Beach, and close to attractions such as the Peabody Essex Museum and The House of the Seven Gables.
This 112 square metre apartment accommodates up to seven guests and features one bedroom, one bathroom, air conditioning, Wi-Fi, a fully equipped kitchen, and free private parking, with easy access to a balcony for outdoor enjoyment.
Garden Apartment For Vacation & Business Travelers - Massachusetts
9.9 393 reviews

Garden Apartment For Vacation & Business Travelers

apartment, Medford
This charming lower-level flat is situated in Medford, just a short drive from both Harvard University and Boston, offering easy access to the city's attractions. The apartment has consistently received excellent ratings for its cleanliness, location and overall experience.
The self-catering property provides 900 sq. ft. of space, comfortably accommodating up to four guests. Enjoy the convenience of a fully equipped kitchen, a private patio area, and access to a range of outdoor amenities, including a fitness centre, a garden, and parking.

Top cities

Best pet friendly Massachusetts holiday rentals

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

The Mermaid Cottage @ The Cape Cod Canal Compound Lodge - Massachusetts
9.2 113 reviews

The Mermaid Cottage @ The Cape Cod Canal Compound Lodge

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.
Clear Pond Suite - Massachusetts
9.5 260 reviews

Clear Pond Suite

apartment, Plymouth
The Clear Pond Suite is located in Plymouth, Massachusetts, just 6.1 miles from Plimoth Plantation and 22 miles from Heritage Museums & Gardens, offering easy access to local attractions. The apartment has received excellent ratings for its cleanliness, location and overall experience.
This one-bedroom flat spans 74 square metres and features a fully equipped kitchen, a private terrace with lake views, and a garden. Guests can enjoy a range of amenities including a swimming pool, free bikes, a picnic area, and on-site activities like fishing and canoeing.
Country Home With Babbling Brook And Pond View- Minutes To Berkshire East Resort - Massachusetts
9.6 136 reviews

Country Home With Babbling Brook And Pond View- Minutes To Berkshire East Resort

apartment, Hawley
This smoke-free holiday home is situated in the mountains, just 15 kilometres from Swift River, Hawley Bog Preserve, and Berkshire East Ski Resort, offering a peaceful escape in a stunning natural setting. It has received excellent user ratings, making it a popular choice for families and groups.
The three-bedroom property, with its 107 square metres of space, comfortably accommodates up to eight guests. It boasts a garden, barbecue facilities, a fireplace, and modern amenities like a fully equipped kitchen and a DVD player, ensuring a relaxing and enjoyable stay.
Bright Studio Near Boston -- T -- Fifa 2026 - Massachusetts
No reviews

Bright Studio Near Boston -- T -- Fifa 2026

studio, Malden
This Malden flat is situated near the T, offering convenient access to Boston's attractions, with Central Square 7.56 kilometres away and the O2 Arena 7.88 kilometres distant.
This one-bedroom flat, measuring 40 square metres, accommodates up to seven guests and features a fully equipped kitchen, on-site parking, and complimentary high-speed Wi-Fi.

Frequently asked questions about holiday rentals in Massachusetts

  • What are the must-see sights in Massachusetts?

    Massachusetts boasts a wealth of historical and cultural attractions. For history buffs, a visit to Boston is essential, exploring sites like 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 association with the Salem Witch Trials are captivating. Beyond the cities, the charming towns of Nantucket and Martha's Vineyard offer beautiful beaches and quaint New England architecture.
  • What are the best Airbnb and holiday rentals in Massachusetts?

    Near Boston Historic Two-bedroom With Modern Amenities, Luxurious Renovated House and 2bed/2bath Apt At Waltham Landing - Middle Unit are the most popular Airbnb and holiday rentals in Massachusetts among travellers.

  • Are there unique natural phenomena in Massachusetts?

    While Massachusetts doesn't have dramatic geological features like massive canyons, its natural beauty is subtle yet striking. The coastline offers dramatic cliffs and sandy beaches. The Berkshires region provides stunning mountain scenery, perfect for hiking and scenic drives. The diverse ecosystems support a wide variety of plant and animal life. Specific locations include the dramatic cliffs of the North Shore and the rolling hills of the Pioneer Valley.
  • 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, as Massachusetts experiences varied conditions throughout the year. Comfortable walking shoes are a must, especially for exploring Boston and other historic towns. Layers of clothing are recommended, as temperatures can fluctuate. Don't forget sunscreen, a hat, and sunglasses, particularly during the summer months. A reusable water bottle is also a good idea, to stay hydrated while exploring.
  • What are the best holiday rentals with a pool in Massachusetts?

    Captain Gosnold Village, The Cozy Carriage House - A+ Location - Luxking and Berkshire Mountain Lodge are the best holiday rentals with a pool in Massachusetts.

  • What famous events or festivals are happening in Massachusetts?

    Massachusetts hosts numerous events throughout the year. The Boston Marathon is a world-renowned athletic event. The Salem Haunted Happenings festival celebrates the city's spooky history. Numerous smaller town festivals and fairs take place throughout the summer and autumn, celebrating local produce and crafts. Specific dates vary annually, so checking local event listings closer to your travel dates is advisable.
  • 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?

    Numerous restaurants across Massachusetts showcase local cuisine. In Boston, look for places specialising in New England clam chowder, lobster rolls, and Boston baked beans. Many restaurants in coastal towns offer fresh seafood. The Berkshires region features farm-to-table restaurants using locally sourced ingredients. Specific restaurant recommendations would require more detail on your preferred location and cuisine.
  • 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?

    Beyond the well-known sites, explore the charming towns of the Berkshires, such as Lenox and Stockbridge, offering beautiful scenery and cultural attractions. The Plimoth Patuxet Museums provide a more immersive experience of early colonial life than just Plymouth Rock. The Cape Cod National Seashore offers stunning beaches and hiking trails away from the more crowded areas.
  • What are the best activities for engaging with locals and understanding their culture in Massachusetts?

    Visiting local farmers' markets provides a great opportunity to interact with residents and sample regional produce. Attending smaller town festivals and fairs offers a chance to experience local traditions and customs. Exploring neighbourhoods beyond the main tourist areas, such as the North End in Boston or the Back Bay, allows for a more authentic experience of daily life.
  • What unique natural landscapes and terrain features can travellers explore in Massachusetts?

    Massachusetts offers diverse landscapes. The coastline features dramatic cliffs, sandy beaches, and salt marshes. Inland, the terrain varies from rolling hills and farmland to the mountainous regions of the Berkshires. The state's many forests and parks provide opportunities for hiking, biking, and wildlife viewing. Specific areas include the Cape Cod National Seashore, the Berkshires, and the Quabbin Reservoir.
  • How many days are ideal for a trip to Massachusetts, and what are some itinerary suggestions?

    The ideal length of a trip depends on your interests. A long weekend (3-4 days) could focus on Boston and its surrounding areas. A week-long trip could incorporate Boston, a coastal town like Salem or Plymouth, and a day trip to a location like the Berkshires. Two weeks would allow for a more in-depth exploration of the state's diverse regions.

Nearby regions

Best Massachusetts holiday rentals with a pool

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

Apt In Downtown Seaport - Massachusetts
No reviews

Apt In Downtown Seaport

apartment, Boston
This Seaport District flat is a 19-minute walk from the Old State House and 1.1 km from Boston South Station, offering easy access to major attractions and public transport.
The 59 square metre one-bedroom apartment sleeps five, features a fully equipped kitchen with dishwasher, in-unit laundry, free Wi-Fi, and access to a swimming pool and fitness centre.
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.
Luxury Salem 2br Apartment | Pool  Gym  Parking - Massachusetts
9.8 9 reviews

Luxury Salem 2br Apartment | Pool Gym Parking

apartment, Salem
This luxury flat in Salem is situated a short walk from Downtown Salem's historic waterfront, shops, and eateries, with convenient access to the MBTA Commuter Rail and Salem Ferry for travel to Boston.
This serviced apartment offers two bedrooms and two bathrooms, accommodating up to five guests, and features a heated seasonal outdoor swimming pool, rooftop terrace, fitness centre, speakeasy lounge, and secure parking.
Breezy Marie - Massachusetts
No reviews

Breezy Marie

house, Plymouth
House rental listing. Your accommodation will be based in Plymouth.
Services and facilities include a kitchen, air conditioning and a fridge. This house in Plymouth has a swimming pool!

Neighborhoods and points of interest in Massachusetts

Best Massachusetts holiday rentals with parking

Pet-friendly Garden Studio ~ 25 Mi To Boston! - Massachusetts
9.0 2 reviews

Pet-friendly Garden Studio ~ 25 Mi To Boston!

studio, Scituate
This studio apartment is located in Scituate, just a short walk from Minot Beach and less than 1.6km from Bassing Beach, offering easy access to the beautiful coastline. North Scituate Beach is just a 4-minute walk away.
The apartment is a comfortable 33 square metres, ideal for two guests, with a fully equipped kitchen, a private entrance, and a washing machine for added convenience. Guests can enjoy free Wi-Fi, cable TV, and air conditioning throughout their stay.
Cozy Hilltown Cottage - Massachusetts
10 213 reviews

Cozy Hilltown Cottage

house, Cummington
This Cummington cottage, situated on a secluded 10-acre plot, is a short drive (approximately 16-48km) from cultural attractions such as MASS MoCA, Shelburne Falls, and Tanglewood.
The self-catering property offers a queen bed, full bathroom, functional kitchen, and sleeper sofa, accommodating up to four guests, and includes private parking, a garden, and internet access.
Island View Lakefront Retreat - Massachusetts
9.5 43 reviews

Island View Lakefront Retreat

apartment, Spencer
This three-bedroom flat in Spencer offers direct lake access and is located within an 8-kilometre drive of Rapscallion brewery and 15 kilometres from TreeHouse brewery.
This well-equipped property accommodates up to five guests and features a kitchen with a fridge, microwave, and dishwasher, alongside air conditioning, off-street parking, and a garden, providing year-round opportunities for seasonal activities and wildlife observation.
10 Minutes To Airport-boston-casino (2g) - Massachusetts
9.7 425 reviews

10 Minutes To Airport-boston-casino (2g)

apartment, Chelsea
This Chelsea apartment is conveniently located in a quiet neighbourhood, within walking distance of the area's attractions. The property has received excellent ratings for cleanliness, location and overall user experience. The two-bedroom flat can comfortably accommodate up to five guests, offering a spacious living area and a dedicated playroom for families. The apartment includes a fully equipped kitchen, a private bathroom, and access to shared amenities, including a living room and designated parking.
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