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Vacation Rentals in Winchester, Virginia

about Winchester

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Winchester, Virginia vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Winchester are added and updated every week!

Compared to hotels, Winchester vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Winchester, Virginia Vacation Rentals and Tourism

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Winchester things to do


Alamo Drafthouse Cinema

First off, I am a total popcorn snob. The popcorn here is FABULOUS (for a movie theater, not in comparison to my homemade of course, I am a PC snob more


Dinosaur Land

Great place for kids and masters of plaster. At $6.oo per person, with cheater admission for kids, Dinosaur Land provides ametuer paleontologists a more


Museum of the Shenandoah Valley

I went here for the first time this past weekend and got the AAA discount upon getting my $7 museum ticket. ~Tea Cafe~ For a little under $13 in total more


Family Drive-In Theatre

My first drive-in movie experience! When I told my girlfriend I had never been, she insisted that we check it out, and I'm glad we did. This is more


State Arboretum of Virginia

Had never heard of the place and passing by when I saw the sign and decided to check it out. What a nice hidden gem. Loved the boxwood garden and more


Winchester Dog Park

Nicely sized dog park with plenty of room for dogs and owners to run around and play catch. We've had good experiences here and our dog loves to get more


Fitness Zone

Shenandoah Tumblers has a gym in this facility and hosted the Shenandoah Invitational Valentine Gymnastics Meet this weekend. My daughter's more


Kidz Play

Kidz Play is an indoor playground. They have moon bounce, inflatable slides, etc. All indoors, a great place to take the kids and beat the heat or cold. more


The Little Gym

The instructors are very nice & my daughter loves coming here. It's definitely an opportunity for her to learn new physical activities and more


Northside Lanes

Smokey, this is not 'Nam. This is bowling. There are rules. Mark it zero! Great place to go bowling. They have 40 lanes! The place looked clean and more


Appleland Sports Center

Bring your golf buddies to Appleland for a fun time! The par 3 course is very fun for all golfers and very well maintained. The range is really good too, more


Abram's Delight

I grew up in Winchester but had never been here until today. The docent led tour was excellent, Susie was very friendly, informative and painted a more


Valerie Hill Vineyard & Winery

Wines were VERY good for such a new vineyard and if you like history with your wine, they hit it out of the park. Very cool building, grounds and more


Sweet Caroline's

As a whole, Sweet Caroline's is a typical dive to see live music. My kinda place-- mohawks - eyeliner - disgruntled youth. And the drinks are cheap. more


Shenandoah Valley Discovery Museum

Spent a couple hours in here with a 15 year old, 10 year old, and 5 year old. All the kids had fun. They had a great time making new friends. Is it me more

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Historic Home in Old Town - charming and modernized
Winchester House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $195 /nt

12 reviews write a review