Choose from 80 vacation rentals located in Winchester, Virginia. Top filters in Winchester include Air conditioner, Internet / Wifi, and Parking. Prices range from $48 to $567 per night. Our most popular vacation rental types near Winchester are Apartment and Hotel.

Top vacation rentals in Winchester

Property grounds
4.8
Outstanding(19 Reviews)
Find the secrets to peace and beauty here!
Bed and Breakfast
 in Winchester
2 guests · 1 bedroom · 1 bath
Garden · Kitchen or Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Winchester? This Bed and Breakfast offers a comfort and style with top-notch amenities, including Air conditioner, Fireplace and Internet / Wifi, and more.

$$$$
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Property building, On site
4.3
Excellent(1,916 Reviews)
La Quinta by Wyndham Winchester
Hotel
 in Winchester
3star
2 queen beds
Pool · Pets allowed · Kitchen or Kitchenette

When traveling to Winchester, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $68 per night.

$$$$
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Property building
3.6
Good(315 Reviews)
Red Roof Inn Winchester, VA
Motel
 in Winchester
1 king bed
Pets allowed · Kitchen or Kitchenette · Air conditioner

This Motel for $67 in Winchester, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property building, On site
3.7
Good(461 Reviews)
Sleep Inn & Suites
Hotel
 in Winchester
4star
1 king bed, 1 sofa bed
Pool · Kitchen or Kitchenette · Air conditioner

Experience the best of Winchester with this Hotel available for $106. This property is equipped with amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Search by amenity

Explore vacation rentals with the most popular amenities in Winchester

Vacation rentals with air conditioning in Winchester

Property building, On site
3.5
Average(1,215 Reviews)
Travelodge by Wyndham Winchester
Hotel
 in Winchester
2star
2 queen beds
Pool · Pets allowed · Kitchen or Kitchenette

Nestled in Winchester, this Hotel is perfect for your next vacation. Enjoy Travelodge by Wyndham Winchester's top-rated amenities, including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Property building
4.3
Excellent(411 Reviews)
Holiday Inn Winchester Southeast-Historic Gateway, an IHG Hotel
Hotel
 in Winchester
3star
2 full beds
Pool · Pets allowed · Kitchen or Kitchenette
Most favorited

The best choice in Winchester for Hotel, for $69 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property building
4.1
Excellent(77 Reviews)
Candlewood Suites Winchester, an IHG Hotel
Hotel
 in Winchester
2star
1 single bed
Pets allowed · Kitchen or Kitchenette · Air conditioner
Most favorited

Nestled in Winchester, this Hotel is perfect for your next vacation. Enjoy Candlewood Suites Winchester, an IHG Hotel's top-rated amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property building, On site
Super 8 by Wyndham Winchester VA
Hotel
 in Winchester
1star
2 full beds
Pets allowed · Kitchen or Kitchenette · Air conditioner

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Winchester, at $67 per night for your next great vacation.

$$$$
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Winchester

Winchester travel guide

Let us help you plan your perfect Winchester vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Winchester, and more.

Frequently asked questions

What is the price range for rentals in Winchester?

Vacation rentals in Winchester have a price range between $48-$567. The average price for rentals in Winchester is $121 per night.

What are the top things to do in Winchester, VA?

Winchester, VA is a great place to visit with plenty of things to do. Here are the top 4 things to do:

  • Visit the Museum of the Shenandoah Valley
  • Explore the trails of the George Washington National Forest
  • Tour the Belle Grove Plantation
  • Relax at the Jim Barnett Park

Whether you're looking for a day of outdoor activities or a day of learning about the history of the area, Winchester, VA has something for everyone!

What are the most popular vacation rental amenities in Winchester, VA?

The most popular vacation rental amenities in Winchester, VA include:

  • Fully equipped kitchen
  • Outdoor spaces with patio or deck
  • High-speed Wi-Fi
  • Smart TV
  • Sound system or speakers

These amenities provide comfort and convenience to visitors while on vacation, allowing them to enjoy their stay without having to worry about finding the necessary items to make their stay enjoyable.

Where is Winchester, VA?

Winchester, VA is located in the northern part of the Shenandoah Valley in Virginia. It is approximately 75 miles west of Washington, D.C. and is part of the Winchester-Frederick County Metropolitan Statistical Area. It is known for its historic architecture, charming downtown, and the Apple Blossom Festival.

What are the best neighborhoods to visit in Winchester, VA?

The best neighborhoods to visit in Winchester, VA are:

  • Old Town Winchester
  • Downtown Winchester
  • Kernstown Battlefield
  • Glen Burnie Historic District

Old Town Winchester is the oldest part of the city and is home to a variety of restaurants, shops, and galleries. Downtown Winchester is the city's main shopping district and is home to a variety of stores, restaurants, and other attractions. Kernstown Battlefield is a preserved Civil War battlefield with interpretive trails and a visitor center. The Glen Burnie Historic District is a historic neighborhood with a variety of historic buildings and homes.

What are the popular shopping destinations in Winchester, VA?

The popular shopping destinations in Winchester, VA are:

  • Apple Blossom Mall
  • Old Town Winchester
  • Winchester Farmers Market

Apple Blossom Mall is the largest shopping mall in the area with a variety of stores, restaurants, and entertainment. Old Town Winchester is a charming historic district with unique boutiques, art galleries, and restaurants. Winchester Farmers Market is a great place to pick up fresh fruits and vegetables, as well as locally made products.

Is Winchester, VA safe to travel to?

Winchester, VA is generally a safe place to travel to. Here are a few safety tips to keep in mind while visiting:

  • Always stay aware of your surroundings.
  • Avoid walking alone at night.
  • Be mindful of suspicious activity.

Following these tips can help you stay safe and enjoy your visit to Winchester, VA.

What is the culture like in Winchester, VA?

Winchester, VA is a city located in the Shenandoah Valley region of Virginia. It is known for its history, culture, and outdoor activities. Here are 5 aspects of the culture in Winchester:

  • The city has a rich history, with many Civil War sites and a vibrant downtown.
  • The city is home to many festivals and events, such as the Apple Blossom Festival and the Handley Regional Library’s Summer Reading Program.
  • The city is home to many art galleries and museums, such as the Museum of the Shenandoah Valley and the Winchester Little Theatre.
  • The city is known for its outdoor activities, such as hiking, biking, and camping.
  • The city has a vibrant music scene, with many local bands and venues.

Where can I find affordable accommodation in Winchester, VA?

Winchester, VA offers a variety of affordable accommodation options, including:

  • The George Washington Hotel
  • The Holiday Inn
  • The Comfort Inn & Suites
  • The Hampton Inn & Suites

These hotels offer great amenities and services, including free Wi-Fi, free parking, and a fitness center. Whether you're traveling for business or pleasure, you can find the perfect place to stay in Winchester, VA.

How can I get around in Winchester, VA?

You can get around Winchester, VA in a variety of ways:

  • Public Transportation: Winchester Transit provides bus service throughout the city.
  • Rideshare: Uber and Lyft are both available in Winchester.
  • Bicycling: There are many bike paths and trails in the area.

What are the must-visit tourist attractions in Winchester, VA?

Winchester, VA is home to several must-visit tourist attractions. These include:

  • Shenandoah Valley Discovery Museum
  • Abram's Delight Museum
  • George Washington's Office Museum
  • Winchester-Frederick County Historical Society

Visitors to Winchester can also explore the city's rich history with a walk through Old Town Winchester, or take a tour of the beautiful Belle Grove Plantation. There are also plenty of outdoor activities, such as hiking and biking, to enjoy in the Shenandoah Valley.

What do I need to know before visiting Winchester, VA?

Before visiting Winchester, VA, it's important to know the following:

  • The city is located in the northern part of the state, near the West Virginia and Maryland borders.
  • The area is known for its outdoor activities, such as hiking and camping.
  • The Shenandoah Valley is a popular destination for tourists.

Winchester has a variety of restaurants, historical sites, and shopping centers. It's also home to a number of festivals throughout the year, including the Shenandoah Apple Blossom Festival. Lastly, the city has an active arts and culture scene, with a number of galleries, theaters, and music venues to explore.

What are the most popular vacation rental amenities in Winchester?

  • Air conditioner
  • Internet / Wifi
  • Parking

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