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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


868 Estate Vineyards

The truffle pairing is excellent! With the tasting, you get to try four handmade chocolate truffles and seven different wines. The wines by themselves more


Dinosaur Land

Totally not worth the 6 bucks per person. Those people who said it was interesting for adults totally lied! Well, I'd give them the benefit of the doubt more


Museum of the Shenandoah Valley

This museum is small, but very engaging. It's a great place to spend an afternoon. Well organized with interesting exhibits. Don't miss the gardens. 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


Dominion Wine Tours

We used this tour for 3 wineries in Loudoun county with a group of four people. It was fantastic all around. The driver was on time, overly polite ( 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

This is my go to place for the driving range. It's always clean and the staff is very friendly. Every time I go there is a sign that says "no Happy 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

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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