Search Holiday Rentals in Winchester

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
2 Jan - 3 Jan
Tomorrow
3 Jan - 4 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Days Inn by Wyndham Hillsboro

Days Inn by Wyndham Hillsboro

10/10 Excellent
"We stayed Christmas night. My son LOVED the perfect bed and my mom fell asleep immediately on (her needed choice) the couch because everything was so inviting. BUT by far, the most wonderful thing was the courteous front desk clerk. He helped my mother, helped with pictures, helped with my great-niece’s little one and offered great solutions for a way for us to have Christmas. We will be forever grateful."
Barbara 1-night trip
Posted 6 days ago
Days Inn by Wyndham Hillsboro

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

What’s there to see and do in Winchester?

While you're exploring the area, Rocky Fork Lake State Park and Rocky Fork Lake are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Serpent Mound and Grant Boyhood Home.

What’s a holiday rental in Winchester like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for families.