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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

Ugh, what a stressful experience. I was treating a friend who was going through a rough time. Neither of us had ever been there before. My friend and I...read more

 

868 Estate Vineyards

The worst experience I have ever had at a vineyard. My group of three girlfriends stopped into 868 Estate Vineyards after a few other vineyards in the area...read 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 and...read more

 

The 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 definitely...read 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. Very...read 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 walking...read 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 a...read more

 

Fitness Zone

Shenandoah Tumblers has a gym in this facility and hosted the Shenandoah Invitational Valentine Gymnastics Meet this weekend. My daughter's gym...read 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 (offering...read 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. My...read 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 follow...read 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 Gilmore...read 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 the...read 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 great...read 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 great...read 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
 
 
 
 
 

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