Compare Vacation Rentals & Rent By Owner Homes in Cheshire, Massachusetts, USA
About Cheshire Vacation Rentals
With more than 59 Cheshire vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Cheshire.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Cheshire, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Cheshire. Places to stay near Cheshire are 874.89 ft² on average, with prices averaging US $349 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Cheshire with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Frequently Asked Questions About Cheshire?
What are the top vacation rentals in Cheshire?
- Charming historic cottage on scenic road to Mt. Greylock
- Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
- Hearts Desire is a furnished whole house in a small, colorful garden center.
- Berkshire Mountain Escape: family retreat open now for fall color and skiing!
- Brooksong, the perfect Berkshires getaway
- 6-BR Berkshires Estate w Pool
- Berkshires Lakefront Retreat by Evergreen Home
- Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
- Harbour House Inn B&B
- New! Lovely Post & Beam home minutes from Lenox & Williamstown, lakes & hiking
How many Rentbyowner vacation rentals are available in Cheshire?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 59 in the Cheshire area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Cheshire.
