Winchester holiday homes

We found 116 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Winchester to find one that's perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and garden. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Winchester

Showing deals for:12 Dec - 19 Dec
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Choose a holiday rental for your Winchester getaway

Learn about the unique charm of Winchester with a stay in a holiday home rental. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Winchester

Are you looking for attractions to visit in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Winchester a fun place to get away to. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Plumpton Park Zoo (7.5 mi / 12 km)
  • Paradocx Vineyard (7.6 mi / 12.2 km)
  • Dove Valley Winery (8.8 mi / 14.2 km)
  • Wyncote Golf Club (11.1 mi / 17.9 km)
  • Back Creek Golf Club (13.1 mi / 21.2 km)
  • Anson B. Nixon Park (15.3 mi / 24.6 km)

Exploring the natural landscape of Winchester

Whether you're an adventurous traveller or just want to appreciate the scenery, Winchester is a great place to get outside. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Fair Hill State Natural Resources Management Area (3.2 mi / 5.1 km)
  • University of Delaware Botanic Gardens (6.2 mi / 10.1 km)
  • Lewis Park (6.4 mi / 10.3 km)
  • Lewden Green Park (11.8 mi / 19 km)
  • Garrett Island Beach (13.5 mi / 21.7 km)
  • Kirkwood Soccer Complex (13.8 mi / 22.2 km)

Travelling to and around Winchester

Book a flight to Baltimore Washington International Airport (BWI), the closest airport, located 54.5 mi (87.7 km) from the city centre.

Frequently asked questions

How much does it cost to rent a holiday home in Winchester?
Season, property type and length of stay are among the factors that can determine the price of a holiday home. Simply click on your travel dates to find your perfect match. From comfy cabins to plush villas, all Bookabach holiday homes offer unbeatable value.
How much does it cost to rent a beach house in Winchester?
The average price for a holiday home close to the beach in Winchester depends on when you'll be there and the size and type of property you want. You can find prices quickly and easily on Bookabach by entering your preferred travel dates. Then use our filters to choose the number of bedrooms and amenities that you prefer, such as air conditioning, WiFi and a pool.
What are the top attractions for families in Winchester?
Keep the kids entertained at these fantastic family-friendly attractions in Winchester:

  • Historical Society of Cecil County
  • Fair Hill State Natural Resources Management Area
  • Cow Pond

How old do you have to be to rent a holiday home in Winchester?
You'll need to check with the Winchester holiday home you're considering on Bookabach as the minimum age differs. However, it's typically 16, 18 or 21.
How long can I rent a holiday home in Winchester for?
How long you can rent a holiday home in Winchester is up to the property. Just enter your desired dates to look at a list of options offering extended stays. With many amenities like full kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to find somewhere perfect to call your home away from home in Winchester.

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