Cheshire vacation rentals
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Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Top rated rentals - Cheshire
Photo gallery for Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Weekend Boys Trip
- 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
Why people love visiting charming 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. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.
Activities and attractions in and around Cheshire
Are you hoping to discover attractions to visit while you're in the area? Venture out of your vacation home and experience everything that makes Cheshire a one-of-a-kind vacation spot. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:
- Jiminy Peak Mountain Resort (6.6 mi / 10.6 km)
- Bousquet Ski Area (11.8 mi / 18.9 km)
- Berkshire East Ski Resort (15.2 mi / 24.5 km)
- Wyndhurst Golf & Club (16 mi / 25.8 km)
- Waubeeka Golf Links (7.6 mi / 12.3 km)
- Clarksburg State Park (12.7 mi / 20.5 km)
Exploring the natural landscape of Cheshire
Whether you're looking for adventure or just want to take in the scenery, Cheshire is a great spot to appreciate mother nature. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:
- Mount Greylock State Reservation Visitor Center (2.6 mi / 4.2 km)
- Mount Greylock (5.2 mi / 8.4 km)
- Mount Greylock State Reservation (5.6 mi / 9 km)
- Savoy Mountain State Forest (8 mi / 12.9 km)
- Pittsfield State Forest (9.9 mi / 15.9 km)
- Natural Bridge State Park (10.8 mi / 17.3 km)
Transportation to and around Cheshire
The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 11.5 mi (18.5 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Hudson, NY (HCC-Columbia County), which is 33.6 mi (54 km) away.