Holiday Rentals in Massachusetts

41544 available vacation rental offers

7 nights
2
1
  • tripcom
  • booking
  • airbnb
  • tripadvisor
  • klook
  • agoda
  • expedia
  • hotelscom
  • hotelscombined
  • eztravel
  • makemytrip
  • rakutentravel
Massachusetts holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Massachusetts holiday rentals: compare the best deals

Best family friendly Massachusetts holiday rentals

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

Seaglass Cottage - Massachusetts
9.8 186 reviews
Massachusetts
06/26 – 06/28
HK$2277/nighttotal: HK$4554 (2 )

Seaglass Cottage

1 2
apartment , Bourne
This charming cottage is situated just 0.2km from the beach in Bourne, offering easy access to the town's amenities, park and the Cape Cod Canal. It has received excellent ratings for cleanliness, location and user experience.
This two-bedroom holiday home can accommodate up to six guests and is equipped with a modern kitchen, air conditioning, a garden and parking. Guests can enjoy a range of activities nearby, including walking trails, shopping centres, other beaches, a water park, and historical sites.
93 M² House ∙ 2 Bedrooms ∙ 1 Guest - Massachusetts
Massachusetts
07/01 – 09/15
HK$957/nighttotal: HK$72732 (76 )

93 M² House ∙ 2 Bedrooms ∙ 1 Guest

2 1
house , Auburn
Vacation rental listing for 1 person. You will be based in Auburn.
Services and facilities: an iron, a fridge and a washing machine. Take advantage of the garden in this house!
Velocity Residence - Massachusetts
9.8 5 reviews
Massachusetts
06/27 – 06/30
HK$2283/nighttotal: HK$6849 (3 )

Velocity Residence

4 3
house , Worcester
Velocity Residence, a house in Worcester, is situated 3.5 kilometres from Worcester Polytechnic Institute and 3 kilometres from Worcester Regional Airport, with the DCU Center Arena & Convention Centre 4.5 kilometres away.
This family-friendly property offers 4 bedrooms, 2 bathrooms, a kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, and parking for up to 10 guests, featuring a private water park and complimentary WiFi.
Spacious 4-bedroom With Four And Half Bathrooms - Massachusetts
10 12 reviews
Massachusetts
07/03 – 07/04
HK$3914/nightfor 1 night

Spacious 4-bedroom With Four And Half Bathrooms

4 4
apartment , Auburn
This four-bedroom, five-bathroom house is situated in Worcester, Massachusetts, approximately 8km from Auburn's shopping areas such as the Auburn Mall and The Shoppes at Blackstone Valley, and a similar distance from attractions including the Goddard Rocket Launching Site and Union Station.
The property, suitable for up to eight guests, offers a spacious layout, a spa, and pet-friendly accommodation, making it ideal for families or groups exploring both Worcester and Auburn's offerings.

Top cities

Best pet friendly Massachusetts holiday rentals

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

Huge Studio In Boston Commons 5bg7 - Massachusetts
9.1 19 reviews
Massachusetts
06/27 – 06/30
HK$2775/nighttotal: HK$8325 (3 )

Huge Studio In Boston Commons 5bg7

1 3
apartment , Boston
This residential flat is situated in the Downtown Boston Theatre District, mere steps from the Commons Park and within a short walk of multiple underground lines, offering unparalleled access to Boston's entertainment and public transport network.
This property, suitable for four guests, features a fully equipped kitchen with a fridge, freezer, and dishwasher, air conditioning, and in-building laundry facilities, with flexible check-in and check-out options available for an additional charge.
Lovely Back Bay 1br, By Blueground - Massachusetts
10 1 review
Massachusetts
09/01 – 05/31
HK$1534/nighttotal: HK$417248 (272 )

Lovely Back Bay 1br, By Blueground

1 2
apartment , Boston
This Back Bay flat is ideally located within a 0.8km radius of the Shops at Prudential Center, Newbury Street, and Copley Place, with Copley Square and Northeastern University a short 2.4km walk away.
The 61 square metre self-catering apartment offers one bedroom, one bathroom, sleeping up to two guests, and includes a fully equipped kitchen, fitness centre access, and housekeeping on request.
Charming House, With Water Views, Private Beach Dining And Shopping - Massachusetts
Massachusetts
07/12 – 08/08
HK$2550/nighttotal: HK$68850 (27 )

Charming House, With Water Views, Private Beach Dining And Shopping

3 4
apartment , Wareham
This Wareham flat offers tranquil lake views and is situated at the gateway to Cape Cod, just 10 kilometres from Onset Beach and the Cape Cod Canal, with easy access to Cape Cod Beaches and Old Silver Beach.
This 3-bedroom property accommodates up to 5 guests, featuring an open-concept layout, a spacious kitchen, air conditioning, internet, and a terrace or balcony, with pets welcome and parking available for your convenience, whilst being close to family-friendly destinations like Water Wizz.
Furnished & Flexible – Perfect For Longer Stays! - Massachusetts
9.8 11 reviews
Massachusetts
10/04 – 10/31
HK$837/nighttotal: HK$22599 (27 )

Furnished & Flexible – Perfect For Longer Stays!

1 2
apartment , New Bedford
This Dartmouth, Massachusetts self-catering property is located less than 0.16 km from Buttonwood Park, offering easy access to Route 6, Route 140, and I-195, putting New Bedford, Newport, Boston, Cape Cod, and Providence within convenient driving distance.
The one-bedroom apartment sleeps two guests, features a 1950s retro décor, a fully equipped kitchen with fridge, freezer and microwave, air conditioning, parking in a one-car garage, and excellent guest reviews for cleanliness and location.

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! Boston's Freedom Trail is a classic, taking you past historical landmarks like the Paul Revere House and Boston Common. Then there's Plymouth, where you can explore Plimoth Patuxet Museums and learn about the Pilgrims. For art and culture, the Museum of Fine Arts in Boston is world-renowned, and Salem offers a fascinating glimpse into the city's witch trial history. Don't forget the beautiful beaches on Cape Cod, like those in Chatham or Provincetown.
  • What are the best Airbnb and vacation rentals in Massachusetts?

    Near Boston Historic Two-bedroom With Modern Amenities, Steps To The Green Line & Minutes From Boston #15 and Luxurious Renovated House are the most popular Airbnb and vacation rentals in Massachusetts among travelers.

  • Are there unique natural phenomena in Massachusetts?

    Massachusetts boasts some lovely natural features. The Berkshires offer stunning mountain scenery, perfect for hiking. The coastline is dramatic, with places like the dramatic cliffs of Race Point Beach on Cape Cod. You can also explore the diverse ecosystems of the many state parks and forests, like the Mount Greylock State Reservation, home to the highest point in Massachusetts.
  • 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 experiences varied conditions. Comfortable walking shoes are a must, especially if you plan on exploring Boston or hiking. Layers of clothing are recommended, as temperatures can change quickly. Don't forget sunscreen, a hat, and sunglasses, even on cloudy days. A reusable water bottle is also essential, especially during warmer months.
  • 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. Many smaller, local festivals take place throughout the year, celebrating everything from food to music. Check local listings for specific dates and events during your visit. The Fourth of July celebrations in many towns are also quite spectacular.
  • 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 delicious local food, explore the North End in Boston for authentic Italian cuisine. You can find classic New England clam chowder and lobster rolls throughout the state. Many restaurants feature fresh seafood, given the state's coastal location. Trying a 'Boston cream pie' is a must for dessert lovers.
  • 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 visiting the charming town of Lenox in the Berkshires, known for its beautiful scenery and cultural attractions like Tanglewood. The Arnold Arboretum in Boston offers a peaceful escape, showcasing diverse plant collections. The Plimoth Patuxet Museums, while well-known for the Pilgrims, is a great place to experience living history. Also, explore the many lighthouses along the coast.
  • 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 locals and sample regional produce. Attending a local sporting event, like a Red Sox game, provides a taste of the city's passion. Exploring smaller towns outside of Boston gives you a chance to meet people and experience a slower pace of life. Many towns hold festivals and events that are perfect for cultural immersion.
  • What unique natural landscapes and terrain features can travellers explore in Massachusetts?

    Massachusetts offers a diverse range of landscapes. The sandy beaches of Cape Cod contrast sharply with the rocky coastline of the North Shore. The rolling hills of the Berkshires provide opportunities for hiking and scenic drives. The state also has numerous forests, wetlands, and ponds, offering diverse wildlife viewing opportunities. Don't forget the islands, like Martha's Vineyard and Nantucket.
  • How many days are ideal for a trip to Massachusetts, and what are some itinerary suggestions?

    A week is a good amount of time to explore Massachusetts, allowing you to see the main attractions in Boston and venture outside the city. A shorter trip of 3-4 days could focus on Boston and its surrounding areas. A possible itinerary could include 2 days in Boston, 1 day in Salem, and 2 days exploring Cape Cod or the Berkshires.

Nearby regions

Best Massachusetts holiday rentals with a pool

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

Cape Cod Falmouth Getaway, Great Harbors, Pool, Close Beaches Aug 10-16 Avail - Massachusetts
10 38 reviews
Massachusetts
08/31 – 09/07
HK$3699/nighttotal: HK$25893 (7 )

Cape Cod Falmouth Getaway, Great Harbors, Pool, Close Beaches Aug 10-16 Avail

3 2
apartment , Falmouth
This family-friendly house is located in East Falmouth, just a short distance from Cape Cod Beaches and Menauhant Beach. The property has received excellent user ratings, making it a popular choice for travellers.
The 130 square metre house has three bedrooms and two bathrooms, comfortably sleeping up to eight guests. Enjoy the modern amenities, including a swimming pool, a tennis court and a fully equipped kitchen, making it ideal for a relaxing and enjoyable stay.
The Fisher: City Access • Kitchen • Gym • W/d - Massachusetts
9.7 46 reviews
Massachusetts
06/26 – 06/28
HK$2429/nighttotal: HK$4858 (2 )

The Fisher: City Access • Kitchen • Gym • W/d

1 2
apartment , Boston
This Boston apartment rental is conveniently located near Boston College, Harvard University, and the Massachusetts Institute of Technology (MIT), with a 5-minute walk to the T subway providing easy access to the city centre.
The one-bedroom, one-bathroom flat sleeps four guests and boasts a fully equipped kitchen, in-unit laundry, two Roku TVs, and access to a large complex with shared amenities including a swimming pool, fitness centre, and multiple lounges.
Charming Groton Farmhouse Apartment - Massachusetts
8.0 1 review
Massachusetts
11/10 – 01/07
HK$1919/nighttotal: HK$111302 (58 )

Charming Groton Farmhouse Apartment

1 2
apartment , Groton
This Groton holiday home, a 13-minute drive (approx. 8km) from the MIT Haystack Observatory and 15-minute drive (approx. 9km) from Kimball Farm, offers a peaceful rural retreat near Beaver Brook Reservation and Silver Lake State Park.
The 102 square metre (1100 sq ft) property comprises one bedroom, one bathroom, a fully equipped kitchen including dishwasher, and a private garden with outdoor furniture; Wi-Fi, air conditioning, a fireplace, and on-site parking are also provided.
Family Friendly South End Suite - Massachusetts
Massachusetts
07/03 – 07/08
HK$9733/nighttotal: HK$48665 (5 )

Family Friendly South End Suite

1 2
apartment , Boston
This South End flat is situated 1.0 kilometre from Boston South Station and 0.96 kilometres from Back Bay, offering proximity to the Boston Tea Party Ship & Museum and the Freedom Trail.
This 111 square metre apartment accommodates up to 15 guests with 2 bedrooms, 2 bathrooms, a fully equipped kitchen, and amenities including air conditioning, a swimming pool, and a fitness centre.

Best Massachusetts holiday rentals with parking

Gorgeouswestwood - Massachusetts
10 1 review
Massachusetts
07/03 – 07/05
HK$1292/nighttotal: HK$2584 (2 )

Gorgeouswestwood

1 2
apartment , Westwood
This one-bedroom flat is situated in Westwood, approximately 21-22 kilometres from Boston landmarks such as Fenway Park and Boston University, with Norwood Memorial Airport located 6.9 kilometres away.
This non-smoking apartment accommodates up to three guests and features a fully equipped kitchen, air conditioning, free private parking, complimentary WiFi, and a terrace or balcony, all within a quiet residential setting with a garden.
2 Bedroom Boston Condo In Jamaica Plain With Parking - Massachusetts
9.7 161 reviews
Massachusetts
07/03 – 07/15
HK$3605/nighttotal: HK$43260 (12 )

2 Bedroom Boston Condo In Jamaica Plain With Parking

2 4
apartment , Boston
This Egleston Square Condo is located in Jamaica Plain, a lively neighbourhood just a short distance from the Boston Museum of Fine Arts and Fenway Park. The property boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay. This two-bedroom flat comfortably sleeps five guests, offering a spacious and well-equipped living space. Amenities include a fully-equipped kitchen, a garden, a swimming pool, a tennis court and a spa, as well as access to bicycles, BBQ facilities and baby strollers upon request.
Modern 3br/ Close To Encore- Everett #2 - Massachusetts
8.6 42 reviews
Massachusetts
06/21 – 06/23
HK$2293/nighttotal: HK$4586 (2 )

Modern 3br/ Close To Encore- Everett #2

3 2
apartment , Everett
This three-bedroom apartment is conveniently located in Everett, just a short distance from the city centre and attractions such as Encore Boston Harbor and TD Garden. It has received very good user ratings and is perfect for families or groups of up to eight people.
The 93 square metre property boasts a modern and stylish design, featuring a well-equipped kitchen with modern appliances, a comfortable living room with a smart TV, and a small deck area for relaxing. Guests can enjoy amenities such as a Jacuzzi, a spa, and a garden, as well as parking and fast Wi-Fi.
Garden Level One Bedroom Apartment - Massachusetts
8.9 22 reviews
Massachusetts
07/18 – 07/19
HK$1519/nightfor 1 night

Garden Level One Bedroom Apartment

1 2
apartment , Brockton
This Brockton garden apartment offers convenient access to Boston attractions, situated approximately 26-31km from landmarks such as the John F. Kennedy Presidential Library and Museum, South Station, and Logan Airport.
The self-catering flat, sleeping up to five guests, includes free Wi-Fi, private parking, a fully equipped kitchen, and a flat-screen TV; it's a non-smoking property.
©2026 cozycozy.com