Chester holiday rentals
Find spaces that suit your style
Find the best place to stay - Chester
The Playhouse: 7,000 Square Feet of Berkshires Modern Luxury and History
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Theatrical Chester will entice you
The area's theatre scene and monuments are just some of the reasons to come on holiday to Chester. This city's hiking, camping and waterfalls draw many visitors. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.
Activities and attractions in Chester
Are you hoping to find attractions to see while you're in town? Venture out of your holiday home and experience everything that Chester has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:
- Wyndhurst Golf & Club (15.4 mi / 24.7 km)
- Bousquet Ski Area (18 mi / 29 km)
- Otis Ridge (8.5 mi / 13.7 km)
- Kennedy Park (16.7 mi / 26.9 km)
- Blandford Ski Area (6.6 mi / 10.6 km)
- Maple Corner Farm Cross Country Ski Area (10.7 mi / 17.1 km)
Exploring the natural landscape of Chester
Whether you're an adventurous traveller or just want to appreciate the scenery, Chester is a great place to get outside. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city centre:
- Otis Reservoir (9.4 mi / 15.1 km)
- October Mountain State Forest (10.2 mi / 16.5 km)
- Goose Pond Reservation (10.7 mi / 17.2 km)
- Look Memorial Park (15.5 mi / 25 km)
- The Mount (16 mi / 25.8 km)
- Smith College Botanic Garden (17.5 mi / 28.2 km)
Transport to and around Chester
The nearest airport is in Westfield, MA (BAF-Barnes Municipal), located 15.4 mi (24.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Pittsfield, MA (PSF-Pittsfield Municipal), which is 18.9 mi (30.4 km) away.