Cheshire Rentals By Owner

There are a lot of options in Cheshire. If you plan on staying in the Cheshire area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Cheshire:

• Berkshire 6BR Estate Pool, Hot Tub, Game Room
• Brooksong, the perfect Berkshires getaway
• 6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
• Lakefront Home on Pontoosuc Lake, the Berkshires
• Renovated Historic Berkshire Gem w/Hot Tub Pool
• Cheshire Cove | Waterfront Kayak Firepit
• Elegant house nestled in the scenic hills of Northern Berkshire County.
• Chic Berkshire Retreat by Evergreen Home
• Charming A-Frame Near all the Best parts of the Berkshires!
• Mountain living, Hot Tub, 1 bedroom apartment

There are many large, family-friendly vacation homes available in Cheshire; however, here are the most popular family rentals listed on our site:

• 19th c. Barn in the Berkshires
• Charming Adams Home Near Dtwn, Trails and More!
• The Revival House
• 2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Yes, there are 52 self-catering vacation homes in Cheshire that have hot tubs, swimming pools, & other amenities.

There are more than 52 luxury villas and vacation homes in or near Cheshire. Filter by price to compare find the most expensive places to stay on Mountsnowvermontrentals.

Yes, there are 52 pet friendly vacation homes and places to stays that are available in or near Cheshire that you may consider.