Windsor vacation rentals
Find the best place to stay - Windsor
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
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Top rated rentals - Windsor
Photo gallery for Sfa Lodge Log Cabin 4 Bd - 2 Ba Nestled In The Woods 5 Mins From Berkshire East
Beautiful Cabin
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
Book a vacation rental for your Windsor getaway
Learn about the unique charm of Windsor with a stay in a private vacation home. 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 hoping to find things to do in the city? Venture out of your vacation home and experience everything that makes Windsor a one-of-a-kind vacation spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:
- 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 an adventurous traveler or just want to take in the scenery, Windsor is a great place to spend some time outside. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city center:
- 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)
Transportation to and around Windsor
The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 13.8 mi (22.2 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Westfield, MA (BAF-Barnes Municipal), which is 28.9 mi (46.5 km) away.