Vacation rentals in Winchester, VA

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Travel insights for vacation rentals in Winchester

Use our HotelsCombined data-powered tips to help you find your next vacation rental in Winchester.

What is the cheapest day to stay in a vacation rental in Winchester?

The cheapest day to stay in Winchester is Tuesday ($41). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is $245.
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Other accommodations in Winchester

Find the perfect vacation rental for your stay in Winchester, VA. There are 76 hotels in Winchester, VA and price data was last updated on September 11, 2025. The average price for a hotel in Winchester, VA is .
Quality Inn
Quality Inn

Quality Inn

1601 Martinsburg Pike, Winchester, VA, United States
2.5 mi from city centre
Free Wi-Fi
Air Conditioning
$82
Avg. per night
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Ans Inn & Suites
Ans Inn & Suites

Ans Inn & Suites

2649 Valley Avenue, Winchester, VA, United States
2.6 mi from city centre
Free Wi-Fi
Air Conditioning
$70
Avg. per night
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Red Roof Inn Winchester, Va
Red Roof Inn Winchester, Va

Red Roof Inn Winchester, Va

991 Millwood Pike, Winchester, VA, United States
1.8 mi from city centre
Free Wi-Fi
Air Conditioning
$59
Avg. per night
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Fairfield Inn & Suites by Marriott Winchester
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

250 Front Royal Pike, Winchester, VA, United States
1.9 mi from city centre
Pool
Free Wi-Fi
Parking
$101
Avg. per night
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Motel 6 Winchester
Motel 6 Winchester

Motel 6 Winchester

2951 Valley Avenue, Winchester, VA, United States
3.0 mi from city centre
Free Wi-Fi
Air Conditioning
$55
Avg. per night
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La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

1055 Millwood Pike, Route 50 East, Winchester, VA, United States
1.8 mi from city centre
Pool
Free Wi-Fi
Parking
$100
Avg. per night
View Deal

Where to stay in Winchester

Explore different neighborhoods and areas within Winchester, VA to find the perfect location for your stay. Map data was last updated on September 11, 2025.
Whether you're visiting Winchester for leisure or business, utilize the map to find vacation rentals close to your ideal location. Clicking on a vacation rental name will take you to a page with pricing, reviews, and more useful information.

Facts about staying in Winchester, VA

Find useful tips and insights about staying in Winchester to help you make the most of your experience. FAQs were last updated on September 11, 2025.

  • How much does a vacation rental in Winchester cost?

    $115 per night is how much a vacation rental in Winchester costs, on average. $38 per night was the cheapest price recently found by our users, though anything for $115 per night or less is a good deal. Keep in mind that Winchester vacation rental prices fluctuate throughout the year: the most expensive month to book is May, and the cheapest time to book is April.

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