Vacation rentals in Winchester, VA
Find deals on 33 vacation rentals in Winchester, VA
Compare 3M+ hotel and accommodation options.
Top rentals in Winchester
Find the perfect vacation rental for your stay in Winchester
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
City Charmer near Historic OldTown Winchester.
Winchester, VA, United States
Guest Room with King Bed for Rent
Stephens City, VA, United States
The Herd's Inn
Winchester, VA, United States
Lofts for weekly rentals! 2 miles from historic downtown.
Winchester, VA, United States
Blue Mountain Cabin, secluded, perfect for couples, near main road
Winchester, VA, United States
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
Winchester, VA, United States
Modern 3br Country Farmhouse
Winchester, VA, United States
Useful insights on Winchester vacation rentals
Get a quick overview on price and accommodation trends for your visit in Winchester
Lowest Vacation Rental Price | $41 |
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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 Season | December | cheapest month to stay |
| High Season | August | most expensive time to stay |
| 61% | expected price decrease | |
| 65% | expected price increase |
Price | $38 - $280 |
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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?
On average, people book vacation rentals in Winchester for stays of around 3 nights.
When is the best time to book a vacation rental in Winchester?
The cheapest month to rent a vacation apartment in Winchester is usually December. The cost of your apartment or rental property can be around 62% cheaper in December vs. the high season.
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 refreshed on a daily basis.