Windsor holiday homes, MA, USA: holiday houses & more

Scroll through and select from holiday rentals in Windsor to find one that's perfect for your trip. Holiday homes offer the best amenities for your stay with friends, family or just your pet, such as a hot tub and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Book a holiday rental for your Windsor getaway

Learn about the unique charm of Windsor with a stay in a holiday home rental. This city is well-known for its restaurants and shopping. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Windsor

Are you looking for attractions to visit during your stay? Venture out of your holiday home and experience everything that Windsor has to offer. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

Berkshire East Ski Resort (11.5 mi / 18.5 km)
Jiminy Peak Mountain Resort (12.9 mi / 20.8 km)
Bousquet Ski Area (13.6 mi / 21.8 km)
Wyndhurst Golf & Club (16.1 mi / 25.9 km)
Waubeeka Golf Links (14.2 mi / 22.9 km)
Kennedy Park (14.8 mi / 23.8 km)

Exploring the natural landscape of Windsor

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Windsor is a great place to spend some time outside. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

Savoy Mountain State Forest (8.1 mi / 13.1 km)
Mount Greylock State Reservation Visitor Center (9.1 mi / 14.6 km)
Mohawk Trail State Forest (10.1 mi / 16.2 km)
Mount Greylock (10.8 mi / 17.4 km)
Mount Greylock State Reservation (11.5 mi / 18.5 km)
October Mountain State Forest (13.1 mi / 21.1 km)

Transport to and around Windsor

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 13.8 mi (22.2 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 28.9 mi (46.5 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Windsor?

A number of factors determine what you'll pay for your holiday home in Windsor, such as the season, length of stay and type of property. But, all Bookabach homes have one thing in common — unbeatable value. Just enter your travel dates to find your home away from home.

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

The average price for a holiday home near the beach in Windsor depends on when you're going and the type and size of property you're looking for. You can easily and quickly find prices on Bookabach by entering your travel dates and destination. Then use the handy filter tool to select the number of bedrooms and amenities important to you, such as WiFi, air conditioning and a hot tub.

What are the top attractions for families in Windsor?

Keep your kids busy at these awesome family-friendly attractions in Windsor:

Tannery Falls
Mount Greylock State Reservation Visitor Centre
Wahconah Falls State Park

How old do you have to be to rent a holiday home in Windsor?

Age restrictions can differ across properties on Bookabach, so be sure to check the rules of the holiday home in Windsor you're considering. But in general, it's 16, 18 or 21.

How long can I rent a holiday home in Windsor for?

It all depends on the Windsor property. To view a list of options offering extended stays, simply enter your dates and number of people into the Bookabach search page. Look forward to having the entire place to yourself, along with the comforts of home like air conditioning, a kitchen and outdoor spaces to run around in. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.