Middlefield holiday rentals, Massachusetts: holiday houses & more

Scroll through and select from holiday rentals in Middlefield to find one that's perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for hanging out with the people that matter most, such as parking and air conditioning. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

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Find the best place to stay - Middlefield

The Playhouse: 7,000 Square Feet of Berkshires Modern Luxury and History

Sleeps 20 · 6 bedrooms · 5 bathrooms

Blue door - entrance to the front house. Walkway on left leads to back house.

In-Town Victorian 5 Bd Front House &/or 6 Bd Back House w/Beach Rights, Skiing

Sleeps 24 · 12 bedrooms · 7+ bathrooms

Top rated rentals - Middlefield

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Find the perfect holiday rental for your Middlefield getaway

Learn about the unique charm of Middlefield with a stay in a holiday home rental. This city has something for everyone. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Middlefield

Do you want to discover attractions to see in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Middlefield a fun place to get away to. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

Wyndhurst Golf & Club (12.9 mi / 20.7 km)
Bousquet Ski Area (14.3 mi / 23 km)
Jiminy Peak Mountain Resort (20.1 mi / 32.3 km)
Otis Ridge (11.5 mi / 18.4 km)
Blandford Ski Area (11.7 mi / 18.8 km)
Kennedy Park (13.5 mi / 21.8 km)

Exploring the natural landscape of Middlefield

Whether you're looking for adventure or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Middlefield. Here are some of the area’s noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

October Mountain State Forest (7.5 mi / 12.1 km)
Goose Pond Reservation (9.9 mi / 16 km)
Otis Reservoir (13.7 mi / 22 km)
The Mount (13.7 mi / 22.1 km)
Naumkeag Museum (15.9 mi / 25.6 km)
Look Memorial Park (16.7 mi / 26.9 km)

How to get to and around Middlefield

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 15.1 mi (24.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Westfield, MA (BAF-Barnes Municipal), which is 19.6 mi (31.6 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Middlefield?

The most sought-after types of holiday rentals in Middlefield are houses. Searching for something different? Vrbo has plenty of options to match our guests' requirements, so you'll see holiday properties in lots of shapes and sizes. The ideal fit is waiting for you — grab yours today.

How much does it cost to rent a holiday rental in Middlefield?

Several things influence how much you'll pay for a holiday rental in Middlefield, like the time of year, length of stay and property type. Still, all our holiday homes have one thing in common — exceptional value. Just enter your travel dates to find your ideal match.

How much does it cost to rent a beach house in Middlefield?

When you travel and the style and size of the property will determine the cost of your beachside stay. Type in your Middlefield travel dates to see all your options on Vrbo. Can't live without a hot tub? Use the filters to choose the amenities and features you want.

What are popular rental amenities in Middlefield?

Some of the most popular rental amenities people look for in Middlefield include a barbecue grill, a garden and mountain views. Whether you're taking a trip with family, friends or even pets, Vrbo holiday homes provide the best amenities for fun and relaxation with your loved ones.

What are the top attractions for families in Middlefield?

Keeping the kiddos entertained during your holiday in Middlefield is a breeze with these family-friendly attractions:

Glendale Falls
Skyline Trail
Littleville Lake

How old do you have to be to rent a holiday rental in Middlefield?

The minimum age can vary across properties on Vrbo, so be sure to check the rules of the holiday rental in Middlefield you want to book. But typically, it's 16, 18 or 21.

How long can I rent a holiday rental in Middlefield for?

The amount of time you can stay in a Middlefield holiday home for depends on each property. Just put in your preferred travel dates to find options that offer long-term stays. They include all the things you need to make your extended holiday more enjoyable like kitchens and laundries. Some holiday homes may also offer discounted weekly or monthly prices, so you can have a longer stay for less.