Where to stay around Cheshire, MA?

Our 2019 property listings offer a large selection of 222 vacation rentals near Cheshire. From 98 Condos/Apartments to 78 Houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Cheshire for a holiday or a weekend are on VRBO.

Can I rent Condos/Apartments in Cheshire?

Yes, of course. VRBO has 98 Condos/Apartments in Cheshire. Our other popular types of vacation rentals in Cheshire include:

  • Houses: 78 rentals available
  • Studios: 14 rentals available
  • Hotels: 13 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Cabins and more.

Can I find a vacation rental with pool in Cheshire?

Yes, you can select your prefered vacation rental with pool among our 99 vacation rentals with pool available in Cheshire. Please use our search bar to access the selection of vacation rentals available.

    Take in the lakeside beauty of Cheshire

    The lake and wildlife create a pretty picture of Cheshire. Well known for its skiing, hiking and restaurants, this romantic city won't disappoint. Many of our vacation rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

    Activities and attractions in Cheshire

    Do you want to discover things to do while you're in town? Venture out of your cozy vacation rental and check out everything that makes Cheshire a fun place to get away. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

    • Waubeeka Golf Links (7.9 mi / 12.7 km)
    • Bas Ridge Golf Course (8.6 mi / 13.8 km)
    • Bousquet Ski Area (11.7 mi / 18.9 km)
    • Clarksburg State Park (12.4 mi / 20 km)
    • Hawley Bog Preserve (13.9 mi / 22.3 km)
    • Kennedy Park (14 mi / 22.5 km)

    Exploring the natural landscape of Cheshire

    Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Cheshire. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

    • Mount Greylock State Reservation Visitor Center (3.2 mi / 5.1 km)
    • Mount Greylock (5.2 mi / 8.4 km)
    • Wahconah Falls State Park (5.4 mi / 8.7 km)
    • Savoy Mountain State Forest (7.5 mi / 12.1 km)
    • Windsor Lake Park (9.1 mi / 14.6 km)
    • Western Gateway Heritage State Park (9.4 mi / 15.1 km)