Winchester vacation rentals

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Best Winchester vacation rentals

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C$ 72 - C$ 177C$ 177 - C$ 281C$ 281 - C$ 386C$ 386 - C$ 490C$ 490+ per night

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Most recommended vacation rentals in Winchester

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Lofts for weekly rentals! 2 miles from historic downtown. - Winchester - Living room
Lofts for weekly rentals! 2 miles from historic downtown.
Winchester, VA, United States
2.0Poor(1)
Apartment
C$ 94+
Check availability
Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly - Winchester - Living room
Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly
Winchester, VA, United States
2.0Poor(1)
Apartment
C$ 200+
Check availability
The Overlook - Winchester - Dining room
The Overlook
Winchester, VA, United States
8.6Very good(6)
Cabin
Free Wi-Fi
C$ 381+
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Colonial Getaway Near Old Town Historic Winchester - Winchester - Building
Colonial Getaway Near Old Town Historic Winchester
Winchester, VA, United States
9.8Wonderful(10)
House
Free Wi-Fi
C$ 301+
Check availability
'Cozy on Cameron!' -Historic Downtown Winchester - Winchester - Bedroom
'Cozy on Cameron!' -Historic Downtown Winchester
Winchester, VA, United States
Apartment
C$ 142+
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Apt movie theater game room treadmill - Winchester - Building
Apt movie theater game room treadmill
Winchester, VA, United States
9.0Wonderful(1)
Apartment
Parking
Free Wi-Fi
C$ 313+
Check availability
Luxury 4br Retreat Kitchen Grill Fireplace - Winchester - Balcony
Luxury 4br Retreat Kitchen Grill Fireplace
Winchester, VA, United States
10Wonderful(2)
House
Parking
Free Wi-Fi
Pet friendly
C$ 648+
Check availability
Sean's Bar - Private Apartment - Winchester - Bedroom
Sean's Bar - Private Apartment
Winchester, VA, United States
Apartment
Parking
Free Wi-Fi
Pet friendly
C$ 109+
Check availability
City Charmer near Historic OldTown Winchester. - Winchester - Dining room
City Charmer near Historic OldTown Winchester.
Winchester, VA, United States
9.8Wonderful(18)
House
Free Wi-Fi
C$ 248+
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WonderClock House downtown vintage duplex w/ porches, steps to Handley Library - Winchester - Living room
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Winchester, VA, United States
9.0Wonderful(6)
Apartment
C$ 510+
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Blue Mountain Cabin, secluded, perfect for couples, near main road - Winchester - Kitchen
Blue Mountain Cabin, secluded, perfect for couples, near main road
Winchester, VA, United States
10Wonderful(19)
Cabin
Free Wi-Fi
C$ 313+
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Modern 3BR Farmhouse in the Country - Winchester - Living room
Modern 3BR Farmhouse in the Country
Winchester, VA, United States
9.4Wonderful(7)
Agritourism
C$ 462+
Check availability
Cameron Grace Brand New 1BR 1BA apt downtown Winchester - Winchester - Living room
Cameron Grace Brand New 1BR 1BA apt downtown Winchester
Winchester, VA, United States
10Wonderful(4)
Apartment
C$ 343+
Check availability
Indigo Blue modern open vibe on tree lined street - Winchester - Living room
Indigo Blue modern open vibe on tree lined street
Winchester, VA, United States
10Wonderful(12)
House
C$ 490+
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Kona's Cozy Cabin — King Bed, Fireplace, Pet Friendly, Near Hiking and Wineries - Winchester - Bedroom
Kona's Cozy Cabin — King Bed, Fireplace, Pet Friendly, Near Hiking and Wineries
Winchester, VA, United States
9.7Wonderful(8)
House
Free Wi-Fi
C$ 303+
Check availability
King Bed Farmhouse Valley Views - Winchester
King Bed Farmhouse Valley Views
Winchester, VA, United States
9.0Wonderful(5)
House
Free Wi-Fi
Pet friendly
C$ 240+
Check availability
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Good to know

Low season

High season

Average price (weeknight)

November
November
C$ 57
Cheapest month to stay with an average 0% drop in price.
Most expensive month to stay with an average 0% rise in price.
Average Sun - Thu price over the last 2 weeks.

KAYAK's top tips for finding Winchester holiday rental deals

FAQs when booking a vacation home in Winchester

  • What types of vacation rentals are available in Winchester?

    There are loads of different property types that you can make your vacation home in Winchester. You’ll find agritourism, apartments, cabins, houses, homestays and villas.

  • Are there any pet-friendly vacation rentals in Winchester?

    There are a number of dog and pet-friendly Winchester vacation rentals, with around 6% allowing you to bring your pet along with you.

  • How much is a vacation rental in Winchester for tonight?

    In the last 72 hours, users have found Winchester vacation rentals for tonight for as low as C$ 297. Search here for similar prices

  • How can I find vacation rentals near me in Winchester?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Winchester?

Our map will help you find the perfect place to stay in Winchester by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Winchester