The best rentals from the top sites, all in one place

We believe finding a vacation rental in Winchester should be easy and not take hours of searching and scrolling. We’ve designed VacationRenter from the ground up to help travelers find the perfect rental faster and easier.

Where to stay in Winchester

Vacation rentals in Winchester

There are 20 vacation rentals near Winchester for all manner or mood of travel, availability of time off, and size of budget. So, if you are hoping for an affordable Winchester vacation, you can find 10% rentals under $100/night. Or if you are willing to splurge on a luxury vacation in Winchester, there are 2 between $385 and $560/night. Whether you are sleeping by yourself or with a significant other, or are travelling with a group of 12 there are short term home and apartment rentals in Winchester to fit your Connecticut vacation needs. The most popular types of short-term rental homes in Winchester are houses, apartments and private rooms. Winchester has been a frequently searched travel destination this year and continues to grow in popularity. VacationRenter offers a wide selection of vacation rental availability from leading travel sites like VRBO (Vacation Rentals By Owner), Homeaway,, and many more. Search your travel dates to find available Winchester vacation homes for your trip.

Home-types in Winchester

Winchester has a variety of property types for you to consider when booking a trip. Here are the most popular property types in Winchester:
- House16 vacation rentals

Points of interests in Winchester

Winchester has several popular points of interest for you to check out when visiting the area. Here are the most popular points of interest in Winchester:
- Patsy Cline Historic House: 104 vacation rentals
- Theatre Royal Winchester: 66 vacation rentals
- The Kernstown Battlefield: 63 vacation rentals
- The Cathedral Office: 61 vacation rentals
- Westgate Museum: 61 vacation rentals
- Winchester City Museum: 60 vacation rentals
- The Great Hall: 60 vacation rentals