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

Your Cozy And Relaxing Retreat - Massachusetts
10 3 reviews
Massachusetts
20/06 – 27/06
$645/nighttotal: $4515 (7 )

Your Cozy And Relaxing Retreat

1 2
apartment , Woburn
This one-bedroom apartment is ideally located in Woburn, just a short drive from Harvard Square, Cambridge College, and the Brattle Theatre, offering easy access to the cultural and historical attractions of the area. The property consistently receives excellent ratings for its cleanliness, location, and overall experience, making it a popular choice for travellers.
The apartment comfortably accommodates two guests and features a fully equipped kitchen, a private hot tub, and a balcony with garden views. Guests can enjoy relaxing evenings by the outdoor fireplace, take advantage of the free Wi-Fi and private parking, and explore the peaceful garden surrounding the property.
Hyatus Luxury Residences Boston Everett Signature Collection - Massachusetts
10 5 reviews
Massachusetts
31/07 – 16/08
$447/nighttotal: $7152 (16 )

Hyatus Luxury Residences Boston Everett Signature Collection

1 1
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.
Private Furnished 1br -- Washer, Dryer -- Easy Access To Boston - Massachusetts
Massachusetts
01/07 – 31/07
$249/nighttotal: $7470 (30 )

Private Furnished 1br -- Washer, Dryer -- Easy Access To Boston

1 2
apartment , Malden
This one-bedroom flat is situated in Malden, offering convenient access to Boston with public transport links a short distance away.
This 50 square metre apartment accommodates up to five guests and features a fully equipped kitchen, private parking, free Wi-Fi, and an in-unit washer and dryer.
18th Century Refurbished Yankee 3 Bedroom Farmhouse In The Berkshires - Massachusetts
10 4 reviews
Massachusetts
01/07 – 10/07
$496/nighttotal: $4464 (9 )

18th Century Refurbished Yankee 3 Bedroom Farmhouse In The Berkshires

3 2
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.

Top cities

Best pet friendly Massachusetts vacation rentals

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

Sleek 3br Boston - World Cup 2026 Escape - Near Franklin Park 60-3 - Massachusetts
9.8 5 reviews
Massachusetts
03/07 – 05/07
$1693/nighttotal: $3386 (2 )

Sleek 3br Boston - World Cup 2026 Escape - Near Franklin Park 60-3

3 13
apartment , Boston
This three-bedroom Boston apartment, near Wollaston Beach, is conveniently located approximately 10.5 kilometres from Fenway Park and 11.5 kilometres from Boston South Station.
The 117 square metre self-catering flat boasts two bathrooms, free Wi-Fi, private parking, and accommodates up to 29 guests, making it ideal for large groups visiting the city.
1 Mi To Downtown Salem: Studio W/ Fire Pit Access - Massachusetts
9.8 25 reviews
Massachusetts
21/06 – 23/06
$403/nighttotal: $806 (2 )

1 Mi To Downtown Salem: Studio W/ Fire Pit Access

1 2
studio , Salem
This Salem apartment, a short 2.4km walk from Salem State College, Glendale Cove Beach, and Salem Pioneer Village, offers easy access to key attractions including Salem Harbour and the Salem Museum.
The 39 square metre self-catering flat features one bedroom, one bathroom, sleeps three, and includes a private patio, fully equipped kitchen, and on-request housekeeping.
Mayflower*sleeps 5*near Beach*firepit*outdoor Shwr*grill - Massachusetts
9.9 134 reviews
Massachusetts
08/08 – 29/08
$445/nighttotal: $9345 (21 )

Mayflower*sleeps 5*near Beach*firepit*outdoor Shwr*grill

1 5
apartment , Plymouth
This charming bungalow is located just a short 5-minute walk from White Horse Beach in Plymouth, making it ideal for enjoying the beautiful coastline. Guests have consistently rated the property excellent for its cleanliness, location, and overall experience.
The bungalow offers a comfortable layout with one bedroom and one bathroom, spanning 51 square metres and accommodating up to 5 guests. Amenities include a fully equipped kitchen, air conditioning, a private garden, parking, and access to a community fire pit, ensuring a relaxing and enjoyable stay.
Walk To Shops & Eats! Attleboro Basecamp - Massachusetts
Massachusetts
24/06 – 29/06
$498/nighttotal: $2490 (5 )

Walk To Shops & Eats! Attleboro Basecamp

3 1
apartment , Attleboro
This Attleboro flat is centrally located between Boston and Providence, offering proximity to Finberg Park, the Attleboro Arts Museum and Sturdy Memorial Hospital, all within 1.6 kilometres.
With a floor area of 117 square metres, this dwelling accommodates up to six guests and features three bedrooms, one bathroom, a kitchen with fridge and microwave, air conditioning, and a treadmill, allowing pets for a £40 fee.

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

86 M² House ∙ 2 Bedrooms ∙ 6 Guests - Massachusetts
Massachusetts
20/06 – 27/06
$563/nighttotal: $3941 (7 )

86 M² House ∙ 2 Bedrooms ∙ 6 Guests

2 2
house , Mashpee
This New Seabury holiday home is situated 2.4 kilometres from South Cape Beach and offers peaceful golf course views, with convenient access to Popponesset Marketplace (3 kilometres) and Mashpee Commons (8.2 kilometres).
This family-friendly cottage provides accommodation for six guests across two bedrooms and two bathrooms, featuring a private patio, communal pool access, air conditioning, a fully equipped kitchen, and daily free tickets to local attractions through Xplorie, including Island Cruises and Whale Watch.
Luxury Apartments By Hyatus At Boston Everett - Massachusetts
10 2 reviews
Massachusetts
12/08 – 14/08
$1524/nighttotal: $3048 (2 )

Luxury Apartments By Hyatus At Boston Everett

2 5
apartment , Everett
This Everett flat offers proximity to key destinations, situated within 4.8 kilometres of Encore Boston Harbor and Assembly Row, with Chelsea Station a 14-minute walk away.
This serviced apartment provides a swimming pool, fitness centre, and rooftop terrace, alongside in-unit laundry and complimentary public area Wi-Fi, with free on-site parking and gas grills for guest convenience.
Salt Winds - Massachusetts
10 9 reviews
Massachusetts
20/06 – 27/06
$642/nighttotal: $4494 (7 )

Salt Winds

1 5
apartment , Bourne
This Bourne flat is conveniently located for exploring Cape Cod's beaches and attractions, with local amenities just moments away.
This family-friendly property accommodates up to six guests with three bedrooms, featuring a private swimming pool, a fully equipped kitchen with a dishwasher, and air conditioning throughout.
Central 1br Apartment Assembly Square Pool Gym Parking Sleep 5 - Massachusetts
Massachusetts
01/07 – 10/07
$790/nighttotal: $7110 (9 )

Central 1br Apartment Assembly Square Pool Gym Parking Sleep 5

1 2
apartment , Somerville
This Somerville flat is situated in the Winter Hill district, offering a 1.4 kilometre walk to Cambridge College and is 4 kilometres from Inman Square and Boston's North Station and TD Garden.
This 65 square metre apartment accommodates up to seven guests and features a kitchen with a fridge, microwave and dishwasher, air conditioning, a swimming pool, garden, fitness centre, and complimentary on-site parking with free Wi-Fi.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts vacation rentals with parking

Trainmaster's Inn - Caboose - Massachusetts
9.4 10 reviews
Massachusetts
09/07 – 10/07
$487/nightfor 1 night

Trainmaster's Inn - Caboose

2 2
cottage , Palmer Town
This Palmer, Massachusetts cottage is ideally situated within 1.6 kilometres of the Quaboag River, the Yankee Flea Market, and Chase Memorial Park, offering easy access to scenic walks, unique shopping, and recreational activities.
The two-bedroom, one-bathroom self-catering property sleeps four guests and includes air conditioning, parking, Wi-Fi, a hairdryer, a desk, and charcoal grills for outdoor cooking, all within a smoke-free environment.
Beautiful 1br Near Encore Boston 8387 - Massachusetts
8.0 1 review
Massachusetts
20/06 – 27/06
$477/nighttotal: $3339 (7 )

Beautiful 1br Near Encore Boston 8387

1 3
apartment , Everett
This Everett flat is conveniently located near the Encore Boston Harbor casino (a 10-minute walk), offering easy access to Seaport Boston (an 11-minute drive, approximately 18km) and major Boston universities (10-15 minutes' drive).
The 65-square-metre (700 sq ft) one-bedroom apartment sleeps up to three guests, boasting a fully equipped kitchen, free in-unit laundry, and a designated parking space; self check-in is available.
Cozy Third-story Apartment In Dtwn Brockton! - Massachusetts
8.8 5 reviews
Massachusetts
20/06 – 23/06
$241/nighttotal: $723 (3 )

Cozy Third-story Apartment In Dtwn Brockton!

1 2
apartment , Brockton
This apartment is located in Brockton, just over 3 kilometres from both Rocky Marciano Stadium and Campanelli Stadium, offering a peaceful retreat away from the city centre. It has received excellent user ratings, making it a popular choice for travellers.
The apartment has one bedroom and one bathroom, covering 65 square metres and accommodating up to three guests. It comes with modern amenities including parking, Wi-Fi, a fully equipped kitchen, and a spa, providing everything you need for a comfortable stay.
Dont Get Stucked In Boston Traffic - Massachusetts
9.6 52 reviews
Massachusetts
19/06 – 22/06
$1965/nighttotal: $5895 (3 )

Dont Get Stucked In Boston Traffic

5 9
apartment , New Bedford
This apartment is located in New Bedford, just 1 kilometre from New Bedford Regional Airport. It has received excellent ratings for its location, cleanliness, and overall experience.
This four-bedroom flat is suitable for families or groups of friends. It features a garden, a balcony, a fully equipped kitchen, a washing machine, air conditioning, free Wi-Fi, satellite TV, and access to a fitness centre and tennis court.
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