Winchester vacation rentals

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Popular amenities for Winchester vacation rentals

Stay near Winchester's top sights

Museum of the Shenandoah Valley72 locals recommend
Shenandoah Valley Discovery Museum34 locals recommend
Bonnie Blue Southern Market & Bakery28 locals recommend
Bright Box Theater28 locals recommend
Martin's Food25 locals recommend
Old Town Winchester25 locals recommend

Quick stats about vacation rentals in Winchester

  • Total rentals

    90 properties

  • Total number of reviews

    6K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    90 properties include access to wifi

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Winchester?

    Yes! Work meets play with ease at over 50 vacation rentals in Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Winchester?

    Four-legged friends are welcome in Winchester. Choose from more than 20 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in apartment rentals in Winchester?

    Experience the best of Winchester with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Winchester have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Winchester. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Winchester have self check-in?

    Absolutely! We offer over 20 apartment rentals with self check-in in Winchester. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly apartment rentals in Winchester?

    Winchester has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

  1. Airbnb
  2. United States
  3. Virginia
  4. Winchester