Where to stay around Cheshire, MA?

Our 2018 property listings offer a large selection of 189 vacation rentals near Cheshire. From 74 houses to 68 condos, 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.

What are the popular point of interests near where I can stay when traveling to Cheshire?

VRBO offers a large selection of vacation rentals near lovely places in Cheshire. From VRBO travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Jiminy Peak: 433 vacation rentals
  • Tanglewood Music Center: 702 vacation rentals
  • Wahconah Falls State Park: 454 vacation rentals
  • Southern Vermont College: 426 vacation rentals
  • Western Gateway Heritage State Park: 332 vacation rentals

But there are many other points of interest around Cheshire listed on VRBO where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent houses in Cheshire?

Yes, of course. VRBO has 74 houses in Cheshire. Our other popular types of vacation rentals in Cheshire include:

  • Condos: 68 rentals available
  • Apartments: 13 rentals available
  • Cottages: 6 rentals available

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

Can I rent golf rental rentals in Cheshire?

Absolutely, VRBO has 119 golf rental rentals in Cheshire. You have also many other possibilities in Cheshire area, including:

  • Ski rentals: 84 rentals
  • Mountain view rentals: 65 rentals
  • Lake view rentals: 19 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with online bookable in Cheshire?

Yes, you can select your prefered vacation rental with online bookable among our 189 vacation rentals with online bookable 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)