Where to stay around Chester, MA?

Our 2018 property listings offer a large selection of 95 vacation rentals near Chester. From 59 Houses to 23 Bungalows, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chester for a holiday or a weekend are on VRBO.

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

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

  • Chester Town Hall: 399 vacation rentals
  • Pittsfield Station: 572 vacation rentals
  • Bas Ridge Golf Course: 522 vacation rentals
  • Glendale Falls: 334 vacation rentals
  • Crane Museum of Papermaking: 504 vacation rentals

But there are many other points of interest around Chester 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 Chester?

Yes, of course. VRBO has 59 Houses in Chester. Our other popular types of vacation rentals in Chester include:

  • Bungalows: 23 rentals available
  • Cabins: 23 rentals available
  • Cottages: 23 rentals available

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

Can I find a vacation rental with pool in Chester?

Yes, you can select your prefered vacation rental with pool among our 13 vacation rentals with pool available in Chester. Please use our search bar to access the selection of vacation rentals available.

    Take in the lush beauty of Chester

    The area's theater scene and monuments are just a few of the reasons to vacation in Chester. Renowned for its hiking, camping and waterfalls, this city welcomes all visitors. 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 Chester

    Do you want to find attractions to visit in the city? Venture out of your cozy vacation rental and check out everything that makes Chester a fun place to get away. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

    • Becket Land Trust Historic Quarry (4 mi / 6.5 km)
    • Chesterfield Gorge (8.3 mi / 13.4 km)
    • Otis Ridge (9.6 mi / 15.5 km)
    • Maple Corner Farm Cross Country Ski Area (11.2 mi / 18 km)
    • Bas Ridge Golf Course (13.5 mi / 21.8 km)
    • Wood's Pond (15.3 mi / 24.7 km)

    Exploring the natural features in Chester

    Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Chester is a great place to spend some time outside. Here are some of the area’s most eye-catching features, all within 30 miles (48.2 km) of the city center:

    • Becket Land Trust Historic Quarry (4 mi / 6.5 km)
    • Chesterfield Gorge (8.3 mi / 13.4 km)
    • Tolland State Forest (10.8 mi / 17.4 km)
    • October Mountain State Forest (11.1 mi / 17.8 km)
    • Goose Pond Reservation (11.8 mi / 19 km)
    • Tyringham Cobble (14.3 mi / 22.9 km)