Massachusetts holiday lettings

We found 15,575 holiday rentals — enter your dates for availability

Discover a selection of 9928 homes, 3113 apartments and other holiday rentals in Massachusetts that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you expect for your stay, which might include a pool and a washer and dryer. No matter what you're looking for, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Popular cities in Massachusetts

Holiday rentals with weekly discounts - Massachusetts

Showing deals for:26 Sept - 3 Oct

Why visit Massachusetts

  • Rich history: Discover Massachusetts' historical landmarks, including the Freedom Trail in Boston and the iconic Plymouth Rock.
  • Stunning scenery: Experience the breathtaking landscapes of the Berkshires and the beautiful beaches along Cape Cod.
  • Cultural experiences: Explore vibrant cities with renowned museums, theatres, and historic colleges like Harvard and MIT.
  • Outdoor activities: Enjoy a variety of outdoor pursuits, from hiking and cycling to sailing and whale watching.
  • Charming accommodations: Choose from a range of delightful holiday rentals, including cottages and stylish condos.

Popular types of accommodation in Massachusetts

If you're pondering the ideal accommodation for your escape to Massachusetts, look no further. Our most sought-after options include private holiday homes, charming cottages, and stylish condos. Whether you're searching for house rentals, cabin retreats, or even monthly lettings, you'll find a diverse range of holiday rentals to suit your needs. Enjoy your stay with the reassurance of transparency and savings at your fingertips.

  • Houses: The top choice for holiday rentals in Massachusetts, offering spacious and comfortable living for families or groups.
  • Cottages: A charming option, these quaint retreats provide a cosy atmosphere, perfect for a peaceful getaway.
  • Condos: Ideal for those seeking modern amenities, these self-contained units often come with shared facilities.
  • Apartments: Conveniently located, apartments are a great choice for tourists wanting to immerse themselves in local culture.
  • Cabins: Rustic and inviting, cabins provide a unique experience, often nestled in nature.**

Top attractions in Massachusetts

Massachusetts offers a delightful blend of outdoor activities, scenic beauty, and romantic getaways. Visitors can explore stunning beaches, urban parks, and historic colleges, providing a rich cultural experience perfect for families and solo travellers alike. Don't miss the opportunity for sightseeing throughout the region, ensuring you capture the essence of this charming state during your holiday.

  • Fenway Park: A historic sports stadium, Fenway Park is a must-visit for sports enthusiasts, offering a vibrant atmosphere filled with baseball culture. Experience the thrill of a live game surrounded by passionate fans, and take in the iconic Green Monster while soaking up the rich history of America's pastime.
  • TD Garden: This premier event venue hosts everything from thrilling sports events to major concerts. With its modern facilities and buzzing atmosphere, TD Garden is perfect for those looking to enjoy high-energy entertainment in the heart of Massachusetts.
  • Harvard University: As one of the world's most prestigious institutions, Harvard University boasts stunning architecture and lush campuses. Immerse yourself in its rich academic culture, explore fascinating museums, and stroll through the historic grounds that have inspired countless scholars.

Things to do recommended for couples

For a romantic getaway in Massachusetts, indulge in a concert at Tanglewood Music Center, relish skiing at Jiminy Peak Mountain Resort, or take a scenic stroll along Sandwich Boardwalk, where you can bask in the beach vibes and embrace the outdoors together.

Things to do recommended for families

Your family vacation in Massachusetts will be filled with excitement at Gillette Stadium, where sports fans unite. Enjoy thrills at Cape Cod Inflatable Park, a fantastic waterpark, and have a blast at Apex Entertainment Center, an arcade adventure zone perfect for all ages.

Things to do recommended for groups

Explore the vibrant atmosphere of Harvard Square for shopping and entertainment, hike along the scenic Cape Cod Rail Trail for a bit of adventure, and enjoy a round of golf at the Foxborough Country Club amidst beautiful outdoor surroundings. Perfect activities for your group getaway!

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate quite a bit. Furthermore, booking an extended stay can often result in significant savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to search by price, location, and type of accommodation.

Where to stay in Massachusetts

Massachusetts offers a delightful blend of history and natural beauty, perfect for a family getaway or a romantic retreat. From the charming streets of Boston to the scenic landscapes of the Berkshires, each region boasts its own unique atmosphere. Enjoy family-friendly attractions, rich historical sites, and picturesque views, making it an ideal destination for a fall weekend escape. With a variety of holiday rentals available, you’re sure to find the perfect base for your adventures.

  • Boston: Boston, a bustling metropolis, is rich in history and culture. Located in the heart of Massachusetts, this vibrant city attracts visitors looking for a dynamic urban experience. With its remarkable educational institutions, music venues, and extensive shopping centres, Boston offers a plethora of activities. Key landmarks include the historic Fenway Park, home to the Boston Red Sox, and the Hynes Convention Center, which hosts various events. Strolling through the Freedom Trail, you'll encounter significant sites that tell the story of America's birth, making it a must-visit for history enthusiasts.
  • Cape Cod: Cape Cod is a picturesque destination known for its stunning coastal scenery and outdoor adventures. Located in southeastern Massachusetts, this charming area is perfect for those seeking a relaxed beach experience. Visitors can indulge in activities like golfing at scenic courses or enjoying thrilling water park attractions. With its beautiful sandy beaches and family-friendly atmosphere, Cape Cod is ideal for seaside relaxation and exploration. Don’t miss the iconic Cape Cod National Seashore, which offers breathtaking views and nature trails.
  • Nantucket: Nantucket, an enchanting island city, provides a serene escape with its stunning landscapes and outdoor activities. Situated off the coast of Massachusetts, this island is renowned for its beautiful beaches and charming historic architecture. Visitors can enjoy golfing on lush courses or explore the picturesque coastline. The island’s family-friendly beaches, such as Jetties Beach, offer excellent opportunities for sunbathing and water sports. With its quaint atmosphere and rich maritime history, Nantucket is a delightful destination for those seeking both relaxation and adventure.

Best time to go to Massachusetts

If you're planning a trip to Massachusetts, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in April and June to July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January27.3°F (-2.6°C)Light RainMostly SunnySlightly LowSlightly Low
February27.3°F (-2.6°C)Light RainMostly SunnyAverageSlightly Low
March38.3°F (3.5°C)Light RainMostly SunnyAverageSlightly Low
April47.5°F (8.6°C)Light RainMostly SunnySlightly HighAverage
May58.3°F (14.6°C)Light RainMostly SunnyAverageAverage
June63.3°F (17.400000000000002°C)Light RainMostly SunnySlightly HighSlightly High
July69.4°F (20.8°C)Light RainMostly SunnySlightly HighSlightly High
August70.7°F (21.5°C)Light RainMostly SunnyAverageSlightly High
September62.4°F (16.900000000000002°C)Light RainMostly SunnyAverageAverage
October56.7°F (13.7°C)Light RainMostly SunnyAverageAverage
November38.8°F (3.8°C)Light RainMostly SunnySlightly LowAverage
December33.6°F (0.9°C)Light RainMostly SunnySlightly LowAverage

What do I need to keep in mind when booking a vacation in 'Massachusetts

If you’re travelling with a group, family, or pets, or if you’re seeking extended stays, be sure to apply the appropriate filters based on your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Massachusetts with a group: Think about how many bedrooms you'll require, as well as additional features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Massachusetts with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with suitable amenities, such as a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Massachusetts: For many, a family holiday wouldn’t be the same without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Massachusetts: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities such as a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform where you can plan new trips, resume your previous arrangements, or manage your travel plans with ease. Your saved or booked properties will be neatly organised into categories such as Potential, Upcoming, or Current Trips. To begin making the most of Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The historical area of Massachusetts awaits your stay

Enjoy the area's museums, history and live music with a rental holiday home in Massachusetts. Renowned for its sporting events, shopping and restaurants, this city welcomes all visitors. Copley Square and Harvard Square are just a couple of the must-see attractions. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Massachusetts

Are you hoping to find top things to see and do during your stay? Venture out of your cosy holiday rental and check out everything that Massachusetts has to offer. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Encore Boston Harbor (16 mi / 25.7 km)
  • New England Aquarium (17.3 mi / 27.9 km)
  • Honey Pot Hill Orchards (6.7 mi / 10.8 km)
  • Butternut Farm Golf Club (6.9 mi / 11.1 km)
  • Fun and Games Family Entertainment Center (7.5 mi / 12.1 km)
  • Massachusetts Horticultural Society's Gardens at Elm Bank (9.7 mi / 15.6 km)

Exploring the beaches and other natural features in Massachusetts

Whether you're an outdoor enthusiast or just want to take in the scenery, Massachusetts is a great place to get outside. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Copley Square (16.1 mi / 26 km)
  • Boston Common (16.5 mi / 26.6 km)
  • Walden Pond (3 mi / 4.9 km)
  • Walden Pond State Reservation (3.1 mi / 5 km)
  • DeCordova Sculpture Park and Museum (3.9 mi / 6.2 km)
  • Minute Man National Historical Park (5.3 mi / 8.5 km)

Transport to and around Massachusetts

Fly into Bedford, MA (BED-Laurence G. Hanscom Field), the closest airport, located 6.3 mi (10.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Boston, MA (BNH-Boston Harbor Seaplane Base), which is 18.4 mi (29.5 km) away.

If you're travelling by train, Lincoln Station, Concord Station and Weston Silver Hill Station are the main stations in the area. You can see more of Massachusetts by jumping on the metro at West Concord Station, Riverside Station or Woodland Station.

Frequently asked questions

What is the best area to stay in Massachusetts when booking a holiday rental?
Dennis is one of the most popular locations to select a holiday home in Massachusetts. Looking for some awesome things to do here? Be sure to visit Cape Cod Museum of Art and Mayflower Beach.
What is the most popular type of holiday rental accommodation in Massachusetts?
Houses are the most popular style of holiday rental in Massachusetts, according to our data. Even if you have a different idea about what you'd like, Vrbo has properties in a variety of sizes and shapes. Compare our options to find your perfect pad.
How much does it cost to rent a holiday rental in Massachusetts?
The average price for a holiday rental in Massachusetts depends on a number of factors, like time of year, length of stay and property type. Whether you're thinking about a sprawling villa with lots of space or a cosy cabin for just you and your sweetheart, just enter your travel dates to view stays with terrific value.
How much does it cost to rent a beach house in Massachusetts?
Prices for beach houses in Massachusetts differ depending on the type and size of the property and when you're travelling. All you have to do is enter your travel dates into Vrbo and how many guests to see your options and prices. From there you can use our filters to tailor your search by ratings, amenities and more.
What are popular rental amenities in Massachusetts?
When it comes to rental amenities that people are on the lookout for in Massachusetts, a microwave oven, a stovetop and a fridge rank highest. With Vrbo holiday homes, you'll have options to suit your style and taste, whether you're going on a holiday with your partner, family members or even pets.
Are there large group holiday rentals in Massachusetts?
Massachusetts has 1,822 holiday homes that can cater to 10 or more guests. These stays come with the privacy and space you need to enjoy good times with friends and family.
What are the top attractions for families in Massachusetts?
You'll find lots of exciting things to see and do with the family in Massachusetts, including:

  • New England Aquarium
  • Fenway Park
  • TD Garden

Can I find two-bedroom holiday rentals in Massachusetts?
Massachusetts has 2,455 two-bedroom holiday rentals to choose from. Enjoy a holiday home with all the privacy and comfort you want at an attractive price on Vrbo.
Are there holiday rentals with WiFi in Massachusetts?
Whether you want to keep up with the latest headlines, make a video call or update your social media, there are 3,853 holiday homes with WiFi in Massachusetts. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How old do you have to be to rent a holiday rental in Massachusetts?
The minimum age allowed can differ between properties on Vrbo, so be sure to look at the rules of the holiday rental in Massachusetts you want to book. But usually, it's 16, 18 or 21.
How long can I rent a holiday rental in Massachusetts for?
It's really down to the Massachusetts property. To view all available options offering extended stays, just enter your travel dates and guest number into the Vrbo search page. Look forward to having the place to yourself, along with the comforts of home like a fully-equipped kitchen and a backyard where the kids can play. Be on the lookout for any long-term stays that offer weekly or monthly discounts.

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