Hotels in Winchester

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Check prices for these dates

Tonight
Dec 30 - Dec 31
Tomorrow
Dec 31 - Jan 1
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Where to stay in Winchester?

Outdoor wedding area
Elk Forge B&B Inn & Day Spa
Elk Forge B&B Inn & Day Spa
2.5 star property
8.8 out of 10, Excellent, (184)
  • cleanliness
    Serene B&B in Elkton with full-service spa and hot tub for a relaxing getaway.
The price is $129
$137 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Elk Forge B&B Inn & Day Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Budget hotels in Winchester and vicinity

Property grounds
Red Roof Inn Perryville

Red Roof Inn Perryville

Red Roof Inn Perryville
2.0 star property
Perryville
8.8 out of 10, Excellent, (124)
The price is $66
$73 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Red Roof Inn Perryville
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Check out reviews of Winchester hotels guests love

Staybridge Suites Wilmington Downtown by IHG

Staybridge Suites Wilmington Downtown by IHG

10/10 Excellent
"The city view is impressive to witness as usual! The staff is always exemplary with the services they provide. Comfortable bed and nice sized TV. Full size refrigerator and freezer came in handy. Spacious room overall and clean bathroom. One of only a couple of hotels that I always look forward to staying at. "
Christopher 2-night trip
Posted 2 days ago
Staybridge Suites Wilmington Downtown by IHG

Frequently asked questions

What accommodations do travelers recommend in Winchester?
Guests like Embassy Suites by Hilton Newark Wilmington South, Red Roof Inn & Suites Newark - University and Sonesta ES Suites Wilmington - Newark.
Can I book a refundable accommodation in Winchester?
If you want the flexibility to change your plans to Winchester, most properties provide refundable* rates you can book. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.
What will the weather in Winchester be like during my vacation?
The warmest months in Winchester are usually July and August with an average temp of 73°F. January and February are the chilliest months when the average temp is 38°F. The rainiest months are August and July.
Why should I book my Winchester hotel through Hotels.com?
There are plenty of reasons to book your Winchester travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.