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Vacation rentals in Winchester, VA

Find deals on 33 vacation rentals in Winchester, VA

Winchester, VA, United States
7 May — 8 May2

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Top rentals in Winchester

Find the perfect vacation rental for your stay in Winchester
Price
C$ 71
C$ 715
Review Score
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6+
7+
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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$ 72
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\'Cozy on Cameron!\' -Historic Downtown Winchester Photo

\'Cozy on Cameron!\' -Historic Downtown Winchester

Winchester, VA, United States

C$ 173
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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$ 84
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Juliana Spa Suite - Entire Main Apartment Photo

Juliana Spa Suite - Entire Main Apartment

Winchester, VA, United States

10.0
C$ 182
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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$ 102
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Colonial Getaway Near Old Town Historic Winchester Photo

Colonial Getaway Near Old Town Historic Winchester

Winchester, VA, United States

9.8
C$ 243
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Get the best value vacation rental in Winchester

These Winchester vacation rentals have the best prices for their ratings
Juliana Spa Suite - Entire Main Apartment Photo

Juliana Spa Suite - Entire Main Apartment

Winchester, VA, United States

10.0
C$ 182
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Modern 3br Country Farmhouse Photo

Modern 3br Country Farmhouse

Winchester, VA, United States

6.0
C$ 462
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Colonial Getaway Near Old Town Historic Winchester Photo

Colonial Getaway Near Old Town Historic Winchester

Winchester, VA, United States

9.8
C$ 243
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Luxury 4br Retreat Kitchen Grill Fireplace Photo

Luxury 4br Retreat Kitchen Grill Fireplace

Winchester, VA, United States

10.0
C$ 456
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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$ 84
The cheapest price for a room in Winchester found in the last 7 days is C$ 84/night. This rate is available with Guest Room with King Bed for Rent.

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 71% lower than the average during this period.

How many operators does momondo search for hotels in Winchester?

As of April 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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