Stays in Winchester, VA

• Winchester Modern

  House · 3 bed · 3.5 bath · sleeps 5

  Winchester, VA

  From $149 a night

  Exact location

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• 101 Charlton Road Winchester, VA 22602 Price: $415,000

  House · 4 bed · 1.5 bath

  Winchester, VA

  No nightly rate published

  • construction materials: vinyl siding
  • foundation: crawl space
  • parking types: driveway

  Exact location

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• 1 E Hart Street Winchester, VA 22601 Price: $299,900

  Townhome · 4 bed

  Winchester, VA

  No nightly rate published

  • foundation: concrete perimeter
  • parking types: driveway
  • fencing: fully

  Exact location

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• 100 Keystone Lane, Unit HOMESITE 1090 Winchester, VA 22603 Price: $446,639

  Villa · 3 bed

  Winchester, VA

  No nightly rate published

  • foundation: slab, other
  • roof: architectural shingle, other
  • window features: low-e, double hung
  • address: 100 keystone lane

  Exact location

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• 100 Vale Court Winchester, VA 22602 Price: $474,900

  House · 4 bed · 2.5 bath

  Winchester, VA

  No nightly rate published

  • flooring: carpet, hardwood
  • heat system: forced air
  • cooling: central a/c
  • fireplace: 1

  City-level location

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• 100 Winns Circle Winchester, VA 22602 Price: $535,000

  House · 4 bed

  Winchester, VA

  No nightly rate published

  • flooring: hardwood, luxury vinyl plank
  • heat system: forced air
  • cooling: central a/c
  • fireplace: 1

  Exact location

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• 1008 S Cameron Street Winchester, VA 22601 Price: $350,000

  House · 4 bed

  Winchester, VA

  No nightly rate published

  • heat system: hot water
  • cooling: other
  • basement: unfinished
  • construction materials: aluminum siding

  Exact location

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• 101 Poe Drive Winchester, VA 22602 Price: $619,900

  Loft · 4 bed

  Winchester, VA

  No nightly rate published

  • address: 101 poe drive
  • subdivision: raven oaks
  • town: winchester
  • state: va

  Exact location

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• 102 Buckwood Lane Winchester, VA 22602 Price: $368,000

  House · 2 bed · 2 bath

  Winchester, VA

  No nightly rate published

  • flooring: laminated
  • heat system: forced air
  • cooling: central a/c
  • stories: 1

  City-level location

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• 102 Primrose Place Winchester, VA 22602 Price: $499,900

  House · 5 bed · 2.5 bath

  Winchester, VA

  No nightly rate published

  • construction materials: vinyl siding
  • foundation: crawl space
  • roof: shingle
  • parking types: attached garage

  City-level location

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• 1022 Heth Place Winchester, VA 22601 Price: $1,239,000

  House · 4 bed · 2 bath

  Winchester, VA

  No nightly rate published

  • heat system: forced air
  • cooling: central a/c
  • fireplace: 4
  • construction materials: other

  City-level location

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• 103 Elaine Drive Winchester, VA 22602 Price: $379,900

  House · 3 bed · 2 bath

  Winchester, VA

  No nightly rate published

  • heat system: forced air
  • cooling: central a/c
  • stories: 1
  • construction materials: vinyl siding

  City-level location

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• 1 Plaid Hill Drive, Unit SHELDON 40-F2 Winchester, VA 22603 Price: $572,990

  House · 4 bed

  Winchester, VA

  No nightly rate published

  • foundation: other, slab
  • roof: other, architectural shingle
  • window features: low-e, double hung
  • address: 1 plaid hill drive

  City-level location

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• 1 Swansong Place, Unit TEAGAN 24-F2 Winchester, VA 22603 Price: $399,990

  Townhome · 3 bed

  Winchester, VA

  No nightly rate published

  • foundation: slab, other
  • roof: architectural shingle, other
  • window features: low-e, double hung
  • address: 1 swansong place

  City-level location

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• 101 Seminole Drive Winchester, VA 22602 Price: $495,990

  House · 4 bed

  Winchester, VA

  No nightly rate published

  • address: 101 seminole drive
  • subdivision: retreat at winding creek
  • town: winchester
  • state: va

  City-level location

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• 101 Tonto Trail Winchester, VA 22602 Price: $349,900

  Townhome · 2 bed

  Winchester, VA

  No nightly rate published

  • flooring: hardwood, tile/brick
  • heat system: heat pump - electric backup
  • cooling: ceiling fan(s), central a/c
  • stories: 1

  City-level location

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• 1013 Orchard Hill Drive Winchester, VA 22601 Price: $299,900

  Townhome · 3 bed

  Winchester, VA

  No nightly rate published

  • construction materials: vinyl siding
  • foundation: crawl space
  • roof: architectural shingle
  • parking types: driveway, on street

  City-level location

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• 1015 Redbud Road Winchester, VA 22603 Price: $1,050,000

  Farmhouse · 4 bed

  Winchester, VA

  No nightly rate published

  • lot description: private, trees/wooded
  • foundation: slab
  • roof: shingle
  • lot features: private, trees/wooded

  City-level location

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• 102 Forest Valley Road Winchester, VA 22602 Price: $597,000

  House · 5 bed

  Winchester, VA

  No nightly rate published

  • heat system: heat pump(s)
  • cooling: central a/c
  • basement: full, unfinished
  • fireplace: 1

  City-level location

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• 102 Geneva Place Winchester, VA 22603 Price: $405,000

  House · 4 bed

  Winchester, VA

  No nightly rate published

  • heat system: heat pump(s)
  • cooling: central a/c
  • stories: 1
  • construction materials: vinyl siding

  City-level location

  Book direct on Shenandoah Valley VA Real Estate

• 102 Green Park Court Winchester, VA 22602 Price: $275,000

  House · 3 bed

  Winchester, VA

  No nightly rate published

  • heat system: baseboard - electric
  • cooling: window unit(s)
  • stories: 1

  City-level location

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• 1024 Front Royal Pike Winchester, VA 22602 Price: $239,000

  House · 2 bed

  Winchester, VA

  No nightly rate published

  • heat system: baseboard - electric
  • cooling: window unit(s)
  • stories: 1
  • construction materials: block

  City-level location

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• 103 E Germain Street Winchester, VA 22601 Price: $245,000

  Townhome · 2 bed

  Winchester, VA

  No nightly rate published

  • flooring: hardwood, carpet
  • heat system: heat pump(s)
  • cooling: central a/c
  • construction materials: wood siding

  City-level location

  Book direct on Shenandoah Valley VA Real Estate

• 103 Renee Lane Winchester, VA 22602 Price: $710,000

  House · 5 bed

  Winchester, VA

  No nightly rate published

  City-level location

  Book direct on Shenandoah Valley VA Real Estate

How prices are computed

Lowest rate the manager has published. Your dates may cost more; the real price is on their site. The "from" figure is the lowest nightly rate the manager published on that listing page when we last fetched it. It excludes taxes, cleaning and other fees, it is not a quote, and it is not live availability.

Updated 2026-10-31 02:20 UTC. Prices and facts are whatever the manager published on their own site.