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Hotels in Winchester

Vacation rentals in Winchester, VA

Find deals on 33 vacation rentals in Winchester, VA

Winchester, VA, United States
2 Mar — 3 Mar2

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Top rentals in Winchester

Find the perfect vacation rental for your stay in Winchester
Price
C$ 58
C$ 736
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6+
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Hostels and cheap hotels in Winchester

These hotels and hostels usually make for a cheap way to stay in Winchester

Homestay - Not a tiny condo, your home awaits

Winchester, VA, United States

C$ 58
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City Charmer near Historic OldTown Winchester. Photo

City Charmer near Historic OldTown Winchester.

Winchester, VA, United States

9.8
C$ 188
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Guest Room with King Bed for Rent Photo

Guest Room with King Bed for Rent

Stephens City, VA, United States

C$ 87
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The Herd's Inn Photo

The Herd's Inn

Winchester, VA, United States

8.6
C$ 199
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Lofts for weekly rentals! 2 miles from historic downtown. Photo

Lofts for weekly rentals! 2 miles from historic downtown.

Winchester, VA, United States

C$ 104
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Blue Mountain Cabin, secluded, perfect for couples, near main road Photo

Blue Mountain Cabin, secluded, perfect for couples, near main road

Winchester, VA, United States

10.0
C$ 215
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Get the best value vacation rental in Winchester

These Winchester vacation rentals have the best prices for their ratings
Luxury 4br Retreat Kitchen Grill Fireplace Photo

Luxury 4br Retreat Kitchen Grill Fireplace

Winchester, VA, United States

10.0
C$ 397
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Modern 3br Country Farmhouse Photo

Modern 3br Country Farmhouse

Winchester, VA, United States

6.0
C$ 411
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Useful insights on Winchester vacation rentals

Get a quick overview on price and accommodation trends for your visit in Winchester

Lowest Vacation Rental Price

C$ 87
The cheapest price for a room in Winchester found in the last 7 days is C$ 87/night. This rate is available with Guest Room with King Bed for Rent.

When to book a vacation rental in Winchester

Check out the information below to find the best deal on a vacation rental in Winchester
Low seasonDecembercheapest month to stay
High seasonAugustmost expensive time to stay
61%expected price decrease
65%expected price increase

Price

C$ 55 - C$ 398

Information about staying in Winchester

Read these important travel tips before booking a vacation rental in Winchester

How long do people typically book vacation apartments for in Winchester?

Those choosing vacation rental apartments in Winchester typically book for at least 3 nights.

When is the best time to book a vacation rental in Winchester?

Vacation apartments in Winchester are often cheapest in December - rental prices can be around 62% lower than the average during this period.

How many operators does momondo search for hotels in Winchester?

As of February 2025, there are 64 operators available to choose from for hotels in Winchester.

When did momondo last update prices for hotels in Winchester?

Prices for hotels in Winchester are updated daily.

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