Compare Vacation Rentals & Airbnb in Massachusetts

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Massachusetts vacation rentals
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41544 Rentals and Airbnb in Massachusetts

Best family friendly Massachusetts vacation rentals

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

Entire Historic Carriage House With Fireplace & Ac - Massachusetts
10 343 reviews
Massachusetts
03/07 – 04/07
$575/nightfor 1 night

Entire Historic Carriage House With Fireplace & Ac

1 4
apartment , Sherborn
The Carriage House is situated in the Historic District of Sherborn, a short distance from nearby colleges and attractions, offering a peaceful retreat in a charming setting. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The self-catering cottage provides comfortable accommodation for up to four guests in one bedroom and one bathroom. Guests can enjoy a range of amenities, including a well-equipped kitchen, a private screened porch, and access to beautiful shared grounds, making it a perfect choice for families or groups looking for a relaxing getaway.
Elegant 2br - 2ba Oasis With Pool & Gym - Massachusetts
10 3 reviews
Massachusetts
27/08 – 25/09
$439/nighttotal: $12731 (29 )

Elegant 2br - 2ba Oasis With Pool & Gym

3 2
apartment , Everett
This centrally located Everett apartment offers easy access to Encore Boston Harbor (a 4-minute drive) and Assembly Row (a 6-minute drive), and is a 14-minute walk from Chelsea station.
The 93-square-metre (1000 sq ft) property boasts six bedrooms, two bathrooms, accommodates six guests, and includes amenities such as a swimming pool, garden, and a fully equipped kitchen.
Fully Furnished, Luxurious Smart Home, 5 Bedrooms W/dedicated Office - Massachusetts
10 1 review
Massachusetts
27/06 – 04/07
$1230/nighttotal: $8610 (7 )

Fully Furnished, Luxurious Smart Home, 5 Bedrooms W/dedicated Office

5 8
apartment , Framingham
This family-friendly holiday home in Framingham is situated within a 6-minute drive of Fun and Games Family Entertainment Center and Shoppers World, with straightforward access to outdoor pursuits at Ashland State Park and Cochituate State Park.
This spacious 5-bedroom, 2.5-bathroom flat offers accommodation for up to 9 guests, featuring a well-equipped kitchen with a full-size refrigerator, oven, stovetop, coffee maker, and ice dispenser, alongside a private terrace, game room with billiards, and on-site amenities including free Wi-Fi and a television.
Ocean View Room @ Beach Resort / Habitat *Hot Tub* - Massachusetts
Massachusetts
26/06 – 28/06
$496/nighttotal: $992 (2 )

Ocean View Room @ Beach Resort / Habitat *Hot Tub*

1 2
apartment , Wareham
This private room at The Flamingo Guest House, within The Onset Beach Compound, offers direct beach access and ocean views in Onset, a short distance from Porter Thermometer Museum and Aptucxet Trading Post Museum.
This 10 square metre flat sleeps two guests and includes a kitchen with a fridge and microwave, air conditioning, a garden, parking, and complimentary daily breakfast, with kayaks, bikes, and paddleboards available for use.

Top cities

Best pet friendly Massachusetts vacation rentals

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

Downtown Beverly 5 Min To Salem - Massachusetts
Massachusetts
19/07 – 24/07
$320/nighttotal: $1600 (5 )

Downtown Beverly 5 Min To Salem

2 4
apartment , Beverly
This Beverly apartment, located downtown, is 3.2km from The House of the Seven Gables and the Peabody Essex Museum, and an 11-minute walk from Dane Street Beach.
This two-bedroom, one-bathroom flat offers 850 square metres of space, sleeps seven guests, includes a fully equipped kitchen, in-unit laundry, private entrance, garden, and free Wi-Fi.
Wonderful 1br In Mission Hill - Massachusetts
8.3 3 reviews
Massachusetts
27/06 – 04/07
$387/nighttotal: $2709 (7 )

Wonderful 1br In Mission Hill

1 2
apartment , Boston
This one-bedroom flat in Mission Hill, Boston, is situated 2.6 kilometres from Fenway Park, 3.5 kilometres from Back Bay's shops and restaurants, and 3.7 kilometres from MIT.
This 50-square-metre apartment accommodates up to three guests and features a fully equipped kitchen with a dishwasher, complimentary WiFi, and on-site laundry facilities.
Bright Newbury Street 1 Bedroom Apartment - Massachusetts
Massachusetts
03/07 – 08/07
$363/nighttotal: $1815 (5 )

Bright Newbury Street 1 Bedroom Apartment

1 2
apartment , Boston
This one-bedroom flat is located on Newbury Street, a short distance from Back Bay, and within 2.4 kilometres of Boston Common and Beacon Hill.
This apartment offers 65 square metres of living space for two guests, featuring air conditioning, a fully equipped kitchen with a fridge and dishwasher, and an in-unit washing machine, located 1.9 kilometres from Fenway Park.
Boston Childrens, Beth Israel, Dana F, Brigham - Massachusetts
8.3 3 reviews
Massachusetts
27/06 – 04/07
$310/nighttotal: $2170 (7 )

Boston Childrens, Beth Israel, Dana F, Brigham

1 2
apartment , Brookline
This Brookline apartment, ideally located near Boston's major hospitals, including Boston Children's Hospital and Brigham and Women's Hospital, is less than 3km from Boston University and the Hynes Convention Centre.
The 65 square metre, one-bedroom flat sleeps seven guests and features a fully equipped kitchen with dishwasher, free Wi-Fi, and a spa; it's also within easy reach of the Museum of Fine Arts and Fenway Park.

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 41544 accommodations in Massachusetts, here are the 4 best rentals with a pool

The Verb Hotel - Massachusetts
9.4 8222 reviews
Massachusetts
03/07 – 04/07
$1214/nightfor 1 night

The Verb Hotel

2 4
hotel , Boston
The Verb Hotel is located in the Fenway neighbourhood of Boston, close to Fenway Park and within easy reach of Copley Square and the Museum of Fine Arts. This 3-star hotel has excellent user ratings for its location, cleanliness, and overall experience.
The hotel offers a comfortable 28 square metre room with one bedroom and one bathroom. Guests can enjoy a range of amenities including a swimming pool, a terrace, a garden, a restaurant, a bar, a fitness centre, and room service.
Hyatus Luxury Residences Boston Everett Signature Collection - Massachusetts
10 5 reviews
Massachusetts
03/08 – 06/08
$674/nighttotal: $2022 (3 )

Hyatus Luxury Residences Boston Everett Signature Collection

1 2
apartment , Everett
This Everett flat is located 3.6 kilometres from Cambridge College and 5.9 kilometres from North Station and TD Garden, with Boston Logan International Airport a mere 4 kilometres away.
This pet-friendly apartment offers 600 square metres of space for up to 7 guests, featuring a private terrace, bar, barbecue facilities, air conditioning, a fully equipped kitchen with a refrigerator and coffee machine, a communal lounge, a swimming pool, and on-site fitness centre, with free Wi-Fi throughout.
Gated Resort Community - Massachusetts
Massachusetts
01/09 – 28/02
$465/nighttotal: $83700 (180 )

Gated Resort Community

2 1
cottage , Westford
This charming cottage is located in Summer Village, a peaceful neighbourhood just 35 minutes north of Boston. The surrounding area offers easy access to both the picturesque countryside and the city's attractions.
This cosy home sleeps up to six guests in two bedrooms and one bathroom. It comes complete with a swimming pool, air conditioning, internet access, and parking. Enjoy the peace and quiet of the cottage, or explore the nearby attractions such as Max's Country Golf and Nashoba Valley Ski Area.
Beautiful Estate With Salt Water Pool  & Pond With Kayaks - Massachusetts
Massachusetts
03/07 – 04/07
$8953/nightfor 1 night

Beautiful Estate With Salt Water Pool & Pond With Kayaks

5 4
apartment , Oak Bluffs
This spacious five-bedroom residence, situated in the private Fresh Pond Estates of Oak Bluffs, offers direct access to a freshwater pond and is conveniently located 3.2 kilometres from Oak Bluffs centre, 152 metres from a bike path, and a five-minute drive from Edgartown and Vineyard Haven.
This family-friendly holiday home, covering 418 square metres and accommodating up to 12 guests, boasts a heated saltwater pool, Jacuzzi, outdoor kitchen, two fully equipped kitchens including a commercial-grade one, and ample outdoor space with a 21-metre deck perfect for enjoying the surroundings.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts vacation rentals with parking

Upscale Penthouse Near Mit Harvard Central Square - Massachusetts
8.4 8 reviews
Massachusetts
12/08 – 14/08
$833/nighttotal: $1666 (2 )

Upscale Penthouse Near Mit Harvard Central Square

1 5
apartment , Cambridge
This one-bedroom apartment is located in Cambridge, a short walk from Central Square and within easy reach of both Harvard University and the Massachusetts Institute of Technology.
The 70 square metre flat is equipped with a fully-equipped kitchen, a washing machine, a TV, and a garden, and it can accommodate up to 9 guests.
Sunny Dog Friendly Union Sq 1brm - Massachusetts
9.4 131 reviews
Massachusetts
07/01 – 12/01
$345/nighttotal: $1725 (5 )

Sunny Dog Friendly Union Sq 1brm

2 2
apartment , Somerville
This Somerville flat is perfectly situated, just a short walk from both the Gilman Square and Union Square T stops, making it easy to explore the city. It has received excellent ratings for location, cleanliness, and overall experience, ensuring a comfortable stay.
The flat has one bedroom and one bathroom, comfortably accommodating up to four guests. It offers a well-equipped kitchen, free parking, and a private outdoor space, perfect for relaxing after a day of exploring the local shops and restaurants.
Private 3-bedroom In Billerica, Cool Ac - Shared Backyard - Basement Occupied - Massachusetts
Massachusetts
03/07 – 04/07
$671/nightfor 1 night

Private 3-bedroom In Billerica, Cool Ac - Shared Backyard - Basement Occupied

3 4
apartment , Billerica
This Billerica flat offers a convenient base, located near Great Brook Farm State Park and Nutting Lake Conservation Land, with Collins Bowladrome and Lowell Memorial Auditorium also within easy reach.
This 139 square metre apartment accommodates up to six guests with three bedrooms and features a dedicated game room, individual thermostats in each bedroom, and an advanced smart-vent AC system, alongside a kitchen equipped with a fridge, microwave oven, and dishwasher, plus a terrace, balcony, garden, and parking.
Downtown Falmouth 1 Bedroom Apartment - Massachusetts
8.8 3 reviews
Massachusetts
23/06 – 25/06
$291/nighttotal: $582 (2 )

Downtown Falmouth 1 Bedroom Apartment

1 2
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.
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