Holiday Rentals in Massachusetts

41544 available vacation rental offers

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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 41544 accommodations in Massachusetts, here are the 4 best family friendly rentals

Magical Little Home In Historic District I Parking I Rustic Luxury I Outdoor Seating - Massachusetts
9.9 24 reviews

Magical Little Home In Historic District I Parking I Rustic Luxury I Outdoor Seating

house, Marblehead
This detached house is situated in Marblehead's historic district, a 19-minute walk from Gas House Beach and approximately 6.4 kilometres from the Peabody Essex Museum.
This property offers 118 square meters of living space, accommodating up to three guests with one bedroom and two bathrooms, and features a fully equipped kitchen, air conditioning, and complimentary Wi-Fi.
Sterling 1br At Everett | Pool & Gym - Massachusetts
No reviews

Sterling 1br At Everett | Pool & Gym

apartment, Everett
This Everett flat is centrally located, offering a 3-kilometre drive to Encore Boston Harbor and a 5-kilometre drive to the shops and restaurants at Assembly Row.
This 46 square metre dwelling accommodates up to four guests and features a communal swimming pool, garden, billiards, and a fully equipped kitchen with a washer and dryer.
Boston Luxury Home +Free Parking  5 Mins To Casino - Massachusetts
9.9 130 reviews

Boston Luxury Home +Free Parking 5 Mins To Casino

apartment, Everett
This Everett apartment, ideally situated near Encore Boston Harbor casino and with easy access to Boston city centre and the North End (approximately 8 km from Logan Airport), offers a convenient base for exploring the area.
The spacious two-level property sleeps 12 guests across five bedrooms and three bathrooms, boasting a game room, bonus den, fully equipped kitchen, high-speed Wi-Fi, and on-site car rental.
Cozy 3br Boston Apt  Pet-friendly W/ Parking  Red Line & I-93 Access 80/3 - Massachusetts
10 3 reviews

Cozy 3br Boston Apt Pet-friendly W/ Parking Red Line & I-93 Access 80/3

apartment, Boston
This Dorchester, Boston flat is conveniently located near the Shawmut subway station (a 4-minute walk) and offers easy access to the Boston Convention and Exhibition Centre (a 14.5-kilometre drive) and Copley Square (also a 14.5-kilometre drive).
The three-bedroom, one-bathroom property sleeps up to 13 guests, features a fully equipped kitchen including a dishwasher, in-unit laundry, and free on-site parking, alongside air conditioning and Wi-Fi.

Top cities

Best pet friendly Massachusetts holiday rentals

Among the 41544 accommodations in Massachusetts, here are the 4 best pet friendly rentals

Sunny 3br Boston 1st-floor Apt  Pet-friendly  Franklin Park & Red Line 558-1 - Massachusetts
8.4 16 reviews

Sunny 3br Boston 1st-floor Apt Pet-friendly Franklin Park & Red Line 558-1

apartment, Boston
This Dorchester, Boston flat is conveniently located near Boston Common and Revere Beach, offering easy access to Fenway Park and TD Garden.
Sleeping up to 13 guests (with extra fees after 6), this three-bedroom property boasts two bathrooms, a fully equipped kitchen including a fridge, microwave, and dishwasher, in-unit laundry facilities, and pet-friendly accommodation.
Stylish South End Studio - Massachusetts
No reviews

Stylish South End Studio

studio, Boston
This studio apartment is situated in Boston's South End, bordering Back Bay, offering convenient access to Northeastern University and the Southwest Corridor Park, with restaurants and live music venues within walking distance.
This 24 square meter studio accommodates up to two guests and features a private bathroom, a kitchen with essential amenities, and is ideal for medical stays or exploring attractions like Fenway Park, located approximately 3.5 kilometers away.
Cozy 3br Worcester Apt  Pet-friendly Near Clark University & I-290 4/1 - Massachusetts
10 1 review

Cozy 3br Worcester Apt Pet-friendly Near Clark University & I-290 4/1

apartment, Worcester
This flat in Worcester's Main South district is located 750 metres from John J. Binienda Memorial Beach and 500 metres from Burnside Fountain, offering convenient access to local landmarks.
This property accommodates up to 13 guests, featuring three bedrooms, one bathroom, a fully equipped kitchen with oven, fridge, and microwave, air conditioning, complimentary Wi-Fi, and on-site parking, with nearby access to Quinsigamond State Park and The Hanover Theatre for the Performing Arts.
Clear Pond Suite - Massachusetts
9.5 257 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.

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! In Boston, you absolutely have to visit the Freedom Trail, a 4-kilometre-long path that takes you past 16 historical landmarks like the Boston Common, Paul Revere's House, and the Old North Church. Then there's Plymouth, with Plymouth Rock and Plimoth Patuxet Museums, offering a glimpse into the early days of the colony. Further afield, Salem's Witch Museum and historical sites are fascinating, and the Berkshires offer stunning natural beauty and cultural attractions like Tanglewood.
  • What are the best Airbnb and vacation 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 vacation rentals in Massachusetts among travelers.

  • Are there unique natural phenomena in Massachusetts?

    Massachusetts boasts some interesting natural features. The dramatic cliffs and coastline of the North Shore are a highlight, particularly around Gloucester and Rockport. The Berkshires offer stunning mountain scenery, perfect for hiking and exploring. While not a unique phenomenon globally, the autumn foliage in the state is spectacular and draws many visitors.
  • 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 can experience varied conditions, even within a single day. Comfortable walking shoes are a must, as you'll likely be doing a lot of exploring on foot. Layers of clothing are essential, including a waterproof jacket. Don't forget sunscreen, a hat, and sunglasses, especially during the summer months. A reusable water bottle is also highly recommended.
  • 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. In the summer, the Boston Harborfest celebrates the city's maritime history with various events. The state also hosts numerous local town fairs and festivals throughout the year, many celebrating harvests and local traditions. Specific dates vary, so checking local 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?

    For classic New England fare, look for restaurants in Boston's North End for excellent Italian-American food. Seafood is a staple, and you'll find many fantastic restaurants along the coast serving fresh catches. Try clam chowder (a creamy soup with clams), lobster rolls (lobster meat in a toasted bun), and Boston baked beans (slow-cooked beans in molasses). Many restaurants throughout the state offer regional variations on these dishes.
  • 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 exploring the charming towns of the Berkshires, like Lenox and Stockbridge, offering beautiful scenery and quaint shops. The Plimoth Patuxet Museums, while known, often get overlooked in favour of Plymouth Rock. The Arnold Arboretum in Boston is a beautiful botanical garden with a vast collection of trees and plants. The Cape Cod National Seashore offers stunning beaches and hiking trails beyond the usual tourist hotspots.
  • 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 residents and sample regional produce. Attending a local event or festival can provide insights into community life. Striking up conversations with people in smaller towns and villages can lead to interesting interactions. Exploring local pubs and restaurants offers opportunities to experience the social side of Massachusetts culture.
  • What unique natural landscapes and terrain features can travellers explore in Massachusetts?

    Massachusetts has a diverse landscape. The coastline offers dramatic cliffs, sandy beaches, and rocky inlets. The Berkshires provide mountainous terrain perfect for hiking and exploring. Cape Cod's unique geography, a long, narrow peninsula, provides a distinct coastal experience. The state's many islands, such as Martha's Vineyard and Nantucket, offer unique natural beauty and wildlife.
  • How many days are ideal for a trip to Massachusetts, and what are some itinerary suggestions?

    The ideal length of stay depends on your interests. A long weekend (3-4 days) allows for exploring Boston and its surroundings. A week (7 days) enables a more in-depth exploration of Boston, a day trip to Salem, and perhaps a visit to Cape Cod or the Berkshires. Two weeks or more would allow for a more relaxed pace and exploration of more remote areas.

Nearby regions

Best Massachusetts holiday rentals with a pool

Among the 41544 accommodations in Massachusetts, here are the 3 best rentals with a pool

Walk To Mit & T Stop! Kendall Square Extended Base - Massachusetts
No reviews

Walk To Mit & T Stop! Kendall Square Extended Base

apartment, Cambridge
This Cambridge flat is located in East Cambridge, a short walk from Kendall Square and the Massachusetts Institute of Technology (MIT), with public transport links including Kendall-MIT Station 550 metres away and Lechmere Station 1.1 kilometres away, and TD Garden a 3-minute drive.
This 102 square metre residence offers two bedrooms, two bathrooms and accommodation for four guests, featuring a fully equipped kitchen, air conditioning, internet, on-site parking, and access to shared amenities such as a swimming pool, deck, patio, and barbecue.
A Timeless Retreat At Historic Crompton House - Massachusetts
No reviews

A Timeless Retreat At Historic Crompton House

apartment, Worcester
This 2-bedroom apartment is located in Worcester's Elm Park district, offering proximity to local attractions with Elm Park 900 meters away and Mechanics Hall 1 kilometre away.
This 158 square meter residence accommodates up to four guests and features a fully equipped kitchen, air conditioning, communal swimming pool, hot tub, garden, and on-site water sports equipment.
Potager Farm Historic Private Townhouse Sleeps 4 With Pool. - Massachusetts
10 12 reviews

Potager Farm Historic Private Townhouse Sleeps 4 With Pool.

apartment, Groton
Potager Farm, a lovingly restored late 18th-century property in rural Groton, Massachusetts, is within walking distance of the Rail Trail and Harry Rich State Forest, and less than 2.4 kilometres from Groton Hill Music Centre.
This 111-square-metre farmhouse offers two bedrooms (sleeping four), a fully equipped kitchen, a private swimming pool, a terrace, and a spa, all within easy reach of Lawrence Academy and The Groton School.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts holiday rentals with parking

Lane's Cove Bijou - Massachusetts
9.9 43 reviews

Lane's Cove Bijou

apartment, Gloucester
This two-bedroom flat in Gloucester's Lane's Cove offers stunning sunset views over the ocean and cove, with a private street-level entrance and a designated driveway parking space.
The accommodation sleeps three guests and features a gourmet kitchen, a cozy gas fireplace, and a luxurious master bedroom suite, with flexible sleeping arrangements provided by a pullout sofa bed.
Two Story Cozy Of Boston Home. - Massachusetts
10 11 reviews

Two Story Cozy Of Boston Home.

apartment, Boston
This six-bedroom Boston residence, situated in Mattapan, approximately 9.6 kilometres from Boston city centre, offers easy access to attractions such as Fenway Park and TD Garden.
The property boasts a spacious layout sleeping up to 12 guests, complete with three bathrooms, a fully equipped kitchen including a dishwasher, keyless entry, garden, parking, and internet access; nearby amenities include shops and restaurants in the Lower Mills neighbourhood.
Peaceful, Modern 3br Home Near Encore Casino, 12min To Boston - Massachusetts
No reviews

Peaceful, Modern 3br Home Near Encore Casino, 12min To Boston

apartment, Everett
This renovated three-bedroom flat at 51 Paris Street in Everett, MA, is conveniently situated approximately 800 metres from Encore Boston Harbor Casino and about 19 kilometres from Downtown Boston.
This accommodation offers space for up to 10 guests with three bedrooms, one bathroom, a fully equipped kitchen including a fridge, microwave oven, and dishwasher, air conditioning, in-unit laundry, and two off-street parking spaces, with pets welcome.
Harvard And Mit Parking Pass King Bed - Massachusetts
No reviews

Harvard And Mit Parking Pass King Bed

apartment, Cambridge
This apartment is located in a Cambridge district, offering convenient access to local attractions and historical sites.
This 74 square meter flat offers two bedrooms, a fully equipped kitchen with a dishwasher and oven, air conditioning, and parking, accommodating up to 9 guests with free WiFi and check-out at 11:00 AM.
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