Winchester Rentals By Owner

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

• Farmhouse living within sight of Lexington - Horse Paddock available
• 4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
• Charming 3-Bedroom House with Pool, WiFi, AC in Tranquil Winchester
• The Perch - NEW/Downtown!
• The Winchester
• College Park Getaway
• 133 S Highland St Apt A
• College Park Getaway
• College Park Bungalow
• College Park Bungalow

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

• Historic Log Cabin - Farm - Near RRG and Lex. Winter retreat rates available
• 4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
• 133 S Highland St Apt A
• 2nd Story Historic Downtown 2BR with Modern Amenities
• The Perch - NEW/Downtown!

Yes, there are 1 self-catering vacation homes in Winchester that have hot tubs, swimming pools, & other amenities.

There are many luxury villas and vacation homes in or near Winchester. Filter by price to compare find the most expensive places to stay on Sequoiacabins.

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