Winchester vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.
0 of 0 items showing
1 of 3 pages

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

    100 properties

  • Total number of reviews

    6.8K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    60 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 60 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 30 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.

  • What are the most popular amenities for Apartment Rentals in Winchester?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 40 homes with wifi, over 20 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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