Holiday Rentals in Winchester
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5 km
33 rentals in Winchester.
Lofts for weekly rentals! 2 miles from historic downtown.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Queen of Winchester Three Bedroom with Upper Level Deck
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Historic District Downtown Winchester
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City Charmer near Historic OldTown Winchester.
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ANS Inn has clean, spacious rooms located on 5 acres with little traffic.
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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This house is a 2 bedroom(s), 2 bathrooms, located in Winchester, VA.
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Colonial Getaway near Old Town Historic Winchester
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Indigo Blue modern open vibe on tree lined street
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Cameron Charmer pristine downtown apt with double master suites
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The Stock Exchange downtown 3rd floor studio apt
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
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Pure Luxury, Grill and Fireplace
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Charming 3-bedroom townhome with AC and WiFi in lovely Winchester
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Luxury Retreat w/ Chef's Kitchen Grill & Fireplace
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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The Blue Door steps from Handley Library
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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"Cozy on Cameron!" -Historic Downtown Winchester
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Full House!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
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Cozy English Basement Apt quiet but close to downtown
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Nostalgia Lane in the heart of the city
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Spacious home, near medical center, Winchester
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Pretty Little Apt by the Train II
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Yellow Submarine trendy basement apt and courtyard
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cameron Grace Brand New 1BR 1BA apt downtown Winchester
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Apt c/ Movie Theater Pool Table Treadmill
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming 3-bedroom townhome with WiFi and AC in Winchester
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Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly
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Scarborough Fair walk to downtown two story apt
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Morocco Loft 2BR overlooking city walking mall
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Find the secrets to peace and beauty here!
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Rosamond nice downtown studio apt
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Charming 3-bedroom house in wonderful Winchester with WiFi, AC
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Showing results 1-33 of 33
Frequently Asked Questions about Winchester
- Yes, here are some popular holiday rentals in Winchester that have a pool:
- Lofts for weekly rentals! 2 miles from historic downtown.
- The Queen of Winchester Three Bedroom with Upper Level Deck
- Historic District Downtown Winchester
- Yes, here are some popular holiday rentals in Winchester that have internet access:
- Lofts for weekly rentals! 2 miles from historic downtown.
- The Queen of Winchester Three Bedroom with Upper Level Deck
- Historic District Downtown Winchester
- The best pet friendly rentals in Winchester are:
- Lofts for weekly rentals! 2 miles from historic downtown.
- ANS Inn has clean, spacious rooms located on 5 acres with little traffic.
- This house is a 2 bedroom(s), 2 bathrooms, located in Winchester, VA.
- Some of the most popular kid friendly rentals in Winchester are:
- Lofts for weekly rentals! 2 miles from historic downtown.
- Historic District Downtown Winchester
- City Charmer near Historic OldTown Winchester.
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