Vacation rentals in Winchester present a unique blend of history, comfort, and local charm. With a variety of rental options available—from cozy cottages to spacious family homes—there's something to suit every travel preference and budget. Visitors can take advantage of the picturesque surroundings, with convenient access to local attractions and outdoor activities. Whether you're planning a romantic getaway or a family retreat, Winchester's vacation rentals offer the perfect base for exploring the region's rich heritage and natural beauty.
Best Winchester Vacation Rentals
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Apt Movie Theater Game Room Treadmill
Apt Movie Theater Game Room Treadmill Winchester is a spacious property set 550 metres from Greenwood UMC and 4 km from Patsy Cline Historic House. The venue comprises 1 bedroom and 1 bathroom.
The apartment is set 4 km from the center of Winchester. Serving American meals, Castiglia's Italian Eatery is about 15 minutes’ walk away. You can get to Washington's Office Museum in a couple of minutes by car. Hagerstown Regional airport is less than 58 minutes' drive away.
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Luxury Basement Apartment La Casa
Overlooking the garden, Luxury Basement Apartment La Casa is withing a 10-minute drive from Historic Fort Loudoun Site in Winchester. The accommodation comprises 1 bedroom and 1 bathroom.
The venue is located in Winchester, a 30-minute walk from its centre. If you feel like visiting the surroundings, check out Handley Regional Library that is 2.8 km from the apartment. Several restaurants nearby, including Popeyes Louisiana Kitchen and China Garden, offer delicious meals and are set 550 metres away. The property is nestled within a short taxi ride from Museum of the Shenandoah Valley. Hagerstown Regional airport is a 60-minute ride away.
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Luxury 4Br Retreat Kitchen Grill Fireplac
From 409$
Luxury 4Br Retreat Kitchen Grill Fireplace Villa is set 4.3 km from Old Town and represents a 3-bedroom venue with a terrace. A fully equipped kitchen with a microwave, a fridge, and kitchenware is included at the accommodation so that guests can cook for themselves.
Handley Regional Library is approximately 10 minutes' drive away. The city centre of Winchester is 4 km away. Castiglia's Italian Eatery is within a 15-minute walk from the villa. You can get to Patsy Cline Historic House in a few minutes by car. The nearest airport is Hagerstown Regional airport, about 80 km away.
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King Bed Farmhouse Valley Views
From 190$
Located about 15 minutes by car from Marker-Miller Orchards, the 2-bedroom The Herd'S Inn offers rooms with mountain views. There is a fully-fitted kitchen with a microwave oven, a refrigerator, and kitchenware while 2 bathrooms are included as well.
The property is 10 minutes' drive from Fellowship Bible Church. You can get to Kernstown Battlefield and Pritchard House Park in a few minutes by car. Hagerstown Regional airport is about 90 km away.
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Pure Luxury
The 4-bedroom Pure Luxury Villa is less than approximately 3 km from Jim Barnett Park. There is a fully furnished kitchen with a microwave oven, a refrigerator, and glassware while 4 bathrooms are included as well.
The centre of Winchester is nearly 4 km from the venue. Washington's Office Museum is 10 minutes' drive away. Serving American meals, Greenwood Grocery & Deli is about 12 minutes’ walk away. You can get to Patsy Cline Historic House in a few minutes by car. The nearest airport is Hagerstown Regional, situated 80 km from the accommodation.
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Modern Log House First Level Primary
Modern Log House Villa is located around 10 minutes by car from Opequon Presbyterian Church, offers views of the mountain and provides guests with an indoor pool. The venue is also fitted with 0 bedrooms and includes a fully equipped kitchen with a refrigerator, a toaster, and kitchenware.
The accommodation is 15 minutes' drive from Abram's Delight. You can get to the Century farm "Marker-Miller Orchards" in a few minutes by car. Hagerstown Regional airport is approximately 90 km from the villa.