Compare Vacation Rentals & Airbnb in Massachusetts

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Massachusetts vacation rentals
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61432 Rentals and Airbnb in Massachusetts

Best family friendly Massachusetts vacation rentals

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

18th Century Refurbished Yankee 3 Bedroom Farmhouse In The Berkshires - Massachusetts
9.8 9 reviews

18th Century Refurbished Yankee 3 Bedroom Farmhouse In The Berkshires

apartment, Rowe
This pet-friendly farmhouse in Rowe, Massachusetts, is conveniently located within walking distance of Pelham Lake Park and Rowe Town Library.
The three-bedroom property sleeps six guests, boasting a fully equipped kitchen, in-unit laundry, a private terrace, and access to kayaking and winter sports equipment; nearby attractions include Berkshire East Ski Area and Honora Winery, a short drive away.
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.
Artist's Camp On Lake Mahkeenac - Massachusetts
9.6 22 reviews

Artist's Camp On Lake Mahkeenac

cabin, Stockbridge
This charming cottage is located on a river, just 3.4 kilometres from the Frelinghuysen Morris House and Studio and 3.8 kilometres from Tanglewood Music Center, making it a great base for exploring Stockbridge's cultural attractions. It has received excellent reviews from previous guests.
The property has two bedrooms and one bathroom, comfortably accommodating up to four guests. The cottage is equipped with a fully equipped kitchen, a terrace, a garden, a fireplace, and a spa, offering a comfortable and relaxing stay.
Captain Morse House Luxury - In Town, Walk To Waterfront, Beach, Pets, 5 Stars - Massachusetts
No reviews

Captain Morse House Luxury - In Town, Walk To Waterfront, Beach, Pets, 5 Stars

house, Edgartown
The Captain Morse House, a substantial residence, is located on North Water Street in Edgartown, Martha's Vineyard, offering direct waterfront views and situated approximately 300 metres from Edgartown's Main Street shopping and dining.
This expansive property sleeps 28 guests with 12 bedrooms and 7 bathrooms, featuring two full kitchens, two dining rooms, and two living rooms, complemented by a spacious garden with seating for 20, two barbecue stations, and complimentary bicycles, beach chairs, and lawn games.

Top cities

Best pet friendly Massachusetts vacation rentals

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

Updated Vintage Bungalow With Incredible Views - Massachusetts
9.9 191 reviews

Updated Vintage Bungalow With Incredible Views

bungalow, Dartmouth
This Dartmouth bungalow, near the University of Massachusetts Dartmouth and Interstate 195, offers easy access to Boston, Providence, and Cape Cod, all within a convenient driving distance.
This 400 sq ft (approx. 37 sq m) self-catering property features a 350 sq ft (approx. 33 sq m) deck, one bedroom, one bathroom, sleeps three, and includes a fully equipped kitchenette, laundry facilities, and panoramic lake views; pets are welcome (upon approval).
Luxury Apt With City Views And Pool - Massachusetts
No reviews

Luxury Apt With City Views And Pool

apartment, Boston
This West End flat is ideally located in Boston, a short walk (less than 1 km) from TD Garden, the Museum of Science, and North Station, with Faneuil Hall and Boston Harbour within easy reach.
The 59 square metre (635 square foot) self-catering apartment offers one bedroom, one bathroom, sleeps three, and includes a fully equipped kitchen, in-unit laundry, air conditioning, and access to a swimming pool and fitness centre.
Beachfront Stay Near Downtown Scituate - Massachusetts
No reviews

Beachfront Stay Near Downtown Scituate

house, Scituate
This beachfront holiday let in Scituate offers direct access to Sand Hills Beach and is located approximately 37 kilometres from the JFK Presidential Library & Museum.
This family-friendly accommodation includes free private parking, WiFi, a shared kitchen, a private balcony with barbecue, and both indoor and outdoor play areas, alongside a private beach area.
Spacious Studio | 1 King Bed | Near Boston Waltham Center - Massachusetts
No reviews

Spacious Studio | 1 King Bed | Near Boston Waltham Center

studio, Waltham
This lakeside studio apartment in Waltham's downtown district offers convenient access to Harvard Square, located 8 kilometers away, and Newbury Street, 9 kilometers distant, with the natural beauty of Boston Common a mere 7 kilometers from your doorstep.
Guests can enjoy complimentary breakfast, on-site fitness facilities, and pet-friendly accommodation with free Wi-Fi, a fully equipped kitchenette including a fridge and microwave, and balcony views, accommodating up to two people with a 11:00 check-out.

Frequently Asked Questions about vacation rentals in Massachusetts

  • What are the must-see sights in Massachusetts?

    Massachusetts boasts a rich history and diverse landscapes. For history buffs, a trip to Boston is essential, including a walk along the Freedom Trail, visiting Faneuil Hall Marketplace, and exploring the historic neighborhoods of Beacon Hill and the North End. 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 captivating. Beyond the cities, 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 2bed/2bath Apt At Waltham Landing - Middle Unit are the most popular Airbnb and vacation rentals in Massachusetts among travelers.

  • What types of vacation rentals are available in Massachusetts?

    If you are planning to visit Massachusetts you need to look for the right accommodations to help you get the right stay. When you are on holiday you need to look for vacation rentals which would provide you with the right experiences. Vacation rentals are available in different types including apartments, lofts, condos, townhouses and even entire homes and cottages. Hence, you need to decide what's best based on your preferences and needs. These apartments and condos are furnished with all modern kitchen and bathroom facilities and amenities offering you the right comfort and convenience.
  • Are there unique natural phenomena in Massachusetts?

    While Massachusetts doesn't have massive geological wonders like some western states, its coastline offers unique natural beauty. The dramatic cliffs of the North Shore, the sandy beaches of Cape Cod, and the rocky shores of Martha's Vineyard and Nantucket are all worth exploring. The diverse ecosystems of the Berkshires, including forests and mountains, also offer unique natural experiences.
  • What are the most popular Airbnbs in Massachusetts?

  • What are the unmissable activities to do in Massachusetts?

    1. Explore the Cape Cod National Seashore - If you are heading to Massachusetts with your partner you can head to Cape Cod National Seashore where you can explore the stunning beaches and park areas of this national park. This is a great way to enjoy a good romantic weekend.

    2. Explore Halibut Point State Park - When you are looking for adventure and activities you can head to Halibut Point State Park where you can do hiking and biking and even camp and make the most of your trip.

    3. Visit Old Sturbridge Village - If you are interested in the history of the state you can visit the Old Sturbridge Village which recreates the life of New Englanders from the 1790s to the 1830s. This is the biggest outdoor history museum in the entire Northeast where you can explore 200 acres of land.
  • What essentials should you bring along for a trip to Massachusetts?

    Pack comfortable walking shoes, as you'll likely be doing a lot of exploring on foot, especially in Boston. Layers are key, as Massachusetts weather can be unpredictable. A light jacket or raincoat is always a good idea, even in summer. Sunscreen and insect repellent are also recommended, depending on the time of year and your activities. Don't forget a camera to capture the beautiful scenery and historical sites.
  • What are the best vacation rentals with a pool in Massachusetts?

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

  • Where is the best place to stay in Massachusetts?

    When you are visiting Massachusetts for the first time you would want to choose Boston as your place to stay. This is because Boston can provide you with the best hotels and rental apartments and condos you can find. Being the largest and the capital city of the state you can ensure that you can find plenty of options to move around. Boston, itself has plenty of local attractions which you can cover. However, it is well connected to other cities and towns which makes it an ideal location to stay when you are in Massachusetts with limited knowledge about how to move around.
  • What famous events or festivals are happening in Massachusetts?

    Massachusetts hosts many events throughout the year. The Boston Marathon is a world-renowned athletic event. The Boston Harborfest is a large-scale celebration of Boston's maritime history. Numerous smaller town festivals and fairs take place across the state, celebrating local culture and produce. Specific dates vary yearly, so checking local event calendars closer to your travel dates is recommended.
  • What are the best rentals for families and kids in Massachusetts?

  • What are popular theme parks in Massachusetts?

    1. Six Flags New England - When you are in Massachusetts you want to ensure that you experience Six Flags New England which is the largest theme park in the state. Also, with tons of thrilling and heart-pumping rides, you can have a great time here even with kids.

    2. Edaville Family Theme Park - If you are looking for family-friendly fun and adventurous day you can head to Edaville Family Theme Park. This is where you can enjoy bumper boats, carousels, roller coasters and even heritage railroad experiences.

    3. Boundless Adventure Zipline and Aerial Park - If you are looking for some zip line adventures you can head to Boundless Adventure Zipline and Aerial Park where you can test your aerial skills and stamina.
  • Where can you find the best restaurants serving local dishes in Massachusetts, and what are the must-try specialties?

    The North End in Boston is known for its excellent Italian restaurants, with many family-owned establishments serving classic dishes. Seafood is a staple in coastal areas; try clam chowder, lobster rolls, and fresh oysters. In the Berkshires, you'll find farm-to-table restaurants showcasing local produce and meats. Look for restaurants specializing in New England fare to experience regional specialties.
  • What are the best rentals or Airbnbs with a jacuzzi in Massachusetts?

  • What are the best events in Massachusetts?

    1. Boston Harborfest - If you are in Massachusetts for the Fourth of July celebrations you can head to Boston for the Boston Harborfest which is one of the largest celebrations. With plenty of family-friendly activities, live entertainment, boat tours and food, drinks and music you can make the most of the event.

    2. Memorial Day Weekend Festival - Memorial Day events are plenty but when you are in Massachusetts you can head to West Tisbury for the Memorial Day Weekend Festival which will provide you with plenty of fun, food, music and live entertainment.

    3. Boston Book Festival - Book lovers can rejoice and make the most of this annual event where you can celebrate the power of words. This event brings together some of the popular authors and speakers and gets more than 30,000 visitors.
  • What are some less-famous attractions in Massachusetts that are worth the visit?

    The Plimoth Patuxet Museums offer a more immersive experience of the 17th-century Plymouth Colony than just a quick visit to Plymouth Rock. The charming towns of Newburyport and Rockport on the North Shore offer beautiful coastal scenery and unique shops. The Mount Greylock State Reservation, home to the highest point in Massachusetts, provides stunning hiking trails and panoramic views.
  • 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. Exploring smaller towns and engaging with shopkeepers and restaurant owners can provide insights into local life. Attending local events and festivals allows for interaction with the community. Consider taking a walking tour led by a local guide to gain a deeper understanding of the area's history and culture.
  • What unique natural landscapes and terrain features can travelers explore in Massachusetts?

    Massachusetts offers a variety of landscapes. The coastline, with its diverse beaches, cliffs, and harbors, is a major draw. The Berkshires provide opportunities for hiking and exploring mountains, forests, and lakes. Cape Cod's unique geography, formed by glacial activity, offers beautiful beaches and marshes. The islands of Martha's Vineyard and Nantucket offer distinct coastal environments.
  • How many days are ideal for visiting Massachusetts, and what are some itinerary suggestions?

    The ideal length of a trip depends on your interests. A long weekend (3-4 days) can focus on Boston and its surrounding areas. A week allows for exploring both Boston and another region, like Cape Cod or the Berkshires. Two weeks would enable a more comprehensive exploration of the state's diverse offerings. Possible itineraries could focus on historical sites, coastal exploration, or a combination of both.
  • How is the weather in Massachusetts in high season?

    Massachusetts' high season is summer (June-August). Expect warm temperatures, often in the 20-30°C range, with occasional humidity. However, the weather can be unpredictable, with periods of sunshine interspersed with showers. Coastal areas tend to be cooler than inland areas. Packing layers is recommended to adapt to changing conditions.

Nearby regions

Best Massachusetts vacation rentals with a pool

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

Historic 1 Bed/in Town/best Location/hot Tub/deck - Massachusetts
9.6 632 reviews

Historic 1 Bed/in Town/best Location/hot Tub/deck

apartment, Plymouth
This historic Plymouth residence, situated in the cultural district, is directly on the town brook walking paths, a short distance (1.6km) from Plymouth's beaches, and within easy reach of the gristmill, Burial Hill, and the John Carver Hotel.
Sleeping up to 12 adults (more children possible), this renovated property boasts a swimming pool, jacuzzi, and hot tub, alongside a fully equipped kitchen, and is perfect for families, offering a terrace, garden, parking and excellent guest reviews.
1 Mile From Main Street And 1.5 Miles To Falmouth Heights Beach. - Massachusetts
No reviews

1 Mile From Main Street And 1.5 Miles To Falmouth Heights Beach.

apartment, Falmouth
This Falmouth Proper property is located 1 kilometre from Main Street's shops and restaurants, and 2.4 kilometres from Falmouth Heights beach.
This two-bedroom flat accommodates six guests and features air conditioning, a swimming pool with an additional fee, and a large garden, with local attractions including the Woods Hole Ferry Terminal and Cape Cod Children's Museum easily accessible.
2 Mi To Beach: Retreat W/ Pool & Grill In Mashpee! - Massachusetts
9.9 34 reviews

2 Mi To Beach: Retreat W/ Pool & Grill In Mashpee!

house, Mashpee
This two-bedroom house is located in Mashpee, just 2.7 kilometres from South Cape Beach and 3.5 kilometres from South Cape Beach State Park.
The 118 square metre property boasts a private pool, a fully equipped kitchen, air conditioning, a garden, and parking, ideal for families or groups of up to four looking for a comfortable and convenient base to explore the area.
Magnificent Waterfront Home With Pool - Massachusetts
9.9 46 reviews

Magnificent Waterfront Home With Pool

apartment, Newburyport
This waterfront holiday home is located just a kilometre from Newbury Beach, Plum Island Beach, and Salisbury Beach State Reservation, providing easy access to the beautiful coastline of Newburyport. The property has received excellent ratings for location, cleanliness, and overall user experience.
The house has three bedrooms, accommodating up to seven guests, and boasts a range of amenities including a swimming pool, terrace, garden, and fireplace. Guests can enjoy stunning views, relax by the pool, prepare meals in the fully equipped kitchen, or explore the nearby Plum Island Point and Parker River National Wildlife Refuge.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts vacation rentals with parking

Farmhouse Guest Apartment - Massachusetts
10 108 reviews

Farmhouse Guest Apartment

apartment, Groton
This one-bedroom apartment is located in a tranquil rural area of Groton, just a short distance from the town centre and a few kilometres from the picturesque Groton Long Point. It has received excellent ratings for location, cleanliness, and overall user experience.
The self-catering property has a private living room, full kitchen, bathroom, and a large bedroom with a desk, comfortably accommodating two guests. The apartment offers a swimming pool, BBQ area, and a garden, perfect for enjoying the beautiful weather and relaxing outdoors.
Walk To Beach Playground Lighthouse North End - Massachusetts
9.7 8 reviews

Walk To Beach Playground Lighthouse North End

apartment, Newburyport
This three-bedroom Newburyport apartment, situated in the North End, is a four-minute walk from Plum Island Beach and within 24-47 kilometres of Salem and Portsmouth.
The 84-square-metre self-catering flat offers a fully equipped kitchen, two bathrooms, private parking, a garden, and accommodates up to seven guests, with free Wi-Fi and cable TV included.
Near The Ferry/ Charming Gem Apt. - Massachusetts
9.9 123 reviews

Near The Ferry/ Charming Gem Apt.

apartment, New Bedford
This New Bedford apartment, ideally located near the ferry to Martha's Vineyard (approximately 16km away), offers easy access to the city centre's restaurants and Brooklawn Park.
The self-catering flat sleeps four adults, featuring a queen bed and sofa bed, a fully equipped kitchen, Netflix and cable TV, and on-street parking; a washer/dryer is available for stays exceeding seven days.
Spacious And Cozy- Near T-station-quiet Neighborhood! - Massachusetts
No reviews

Spacious And Cozy- Near T-station-quiet Neighborhood!

apartment, Malden
Apartment rental listing. Your accommodation will be located in Malden.
Facilities and services include an iron, free parking and a kitchen. Take advantage of the air conditioning in this apartment!
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