Places to stay in Winchester, VA

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Winchester, VA place to stay
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114 Best places to stay in Winchester, VA

Best family friendly Winchester, VA lodging

Among the 114 accommodations in Winchester, VA, here are the 4 best for families

Cameron Charmer Pristine Downtown Apt With Double Master Suites - Winchester, VA
9.6 8 reviews
Winchester, VA
18/10 – 22/10
£208/nighttotal: £832 (4 )

Cameron Charmer Pristine Downtown Apt With Double Master Suites

2 2
apartment , Winchester
This Winchester holiday home is conveniently located within a 1.6km walk of the Patsy Cline Historic House, the Shenandoah Valley Discovery Museum, and George Washington's Office.
The two-bedroom property, sleeping four guests, boasts three bathrooms, a fully equipped kitchen with microwave and dishwasher, on-site parking, a Smart TV, in-unit laundry, and is within easy reach of attractions such as the Bright Box Theatre and Old Court House Civil War Museum.
Dreamweaver
Bright 1br  
2 Blocks To Walking Mall - Winchester, VA
9.7 46 reviews
Winchester, VA
18/10 – 22/10
£148/nighttotal: £592 (4 )

Dreamweaver Bright 1br 2 Blocks To Walking Mall

1 2
apartment , Winchester
This Winchester city centre flat is situated two blocks from the pedestrian mall, offering easy access to shops, restaurants, and the Handley Library.
The self-catering apartment, sleeping up to three guests, features a queen-sized bed, a futon, free on-site parking, and is close to attractions such as the Museum of the Shenandoah Valley and Skyline Drive.
New Charming 3-bedroom  2 Full Bath And 1 Half Bedrooms Single Family  House - Winchester, VA
8.8 9 reviews
Winchester, VA
27/06 – 04/07
£204/nighttotal: £1428 (7 )

New Charming 3-bedroom 2 Full Bath And 1 Half Bedrooms Single Family House

3 2
apartment , Winchester
This Winchester townhome, near Red Bud Run and Jim Barnett Park, offers easy access to the Shenandoah Valley Discovery Museum and Nalls Farm Market.
Sleeping up to 30 guests, this three-bedroom, four-bathroom property includes a king, queen, and full-size bed, an office with a futon, in-unit laundry, WiFi, air conditioning, and parking, making it ideal for large groups visiting Winchester.
Peaceful Family Retreat In The Heart Of Winchester - Winchester, VA
10 73 reviews
Winchester, VA
18/10 – 24/10
£90/nighttotal: £540 (6 )

Peaceful Family Retreat In The Heart Of Winchester

1 4
apartment , Winchester
This Winchester basement flat offers a private suite with keycode access, situated in a quiet neighbourhood a short drive from local shops and entertainment.
The self-contained apartment sleeps four, featuring a queen-size memory foam bed and bunk beds, a full bathroom, and board games; responsive hosts ensure a comfortable stay.

Top Accommodations with a Swimming Pool in Winchester, VA

Choosing accommodation in Winchester, VA with a swimming pool means a proper swim in the heart of the city is always an option for you.

Winchester Farm - Winchester, VA
10 10 reviews
Winchester, VA
18/10 – 22/10
£523/nighttotal: £2092 (4 )

Winchester Farm

1 2
apartment , Winchester
This Winchester farmhouse, sleeping six guests across three bedrooms and two bathrooms, is situated [Insert precise location within Winchester, e.g., near the city centre, 5km from Winchester Cathedral, or specify a district and distance to a landmark].
The self-catering property boasts a swimming pool, fitness centre, and ample parking, along with WiFi and air conditioning, perfect for families seeking a relaxing country escape near Winchester.

Frequently asked questions about accommodations in Winchester, VA

  • What are the top attractions and must-see sites in Winchester, VA?

    Winchester is packed with history! You've got to see the Old Town, with the historic buildings and the iconic Court House. The Museum of the Shenandoah Valley is a must-visit for art and history buffs. And don't miss the Shenandoah Valley Battlefields State Park, where you can explore the grounds of important Civil War battles.
  • What are the best places to stay in Winchester, VA?

    Among the places to stay in Winchester, VA, The George Washington - A Wyndham Grand Hotel, Hampton Inn Winchester and Holiday Inn Winchester Se-historic Gateway By Ihg are the most popular ones.

  • Which cultural festivals and seasonal events should visitors attend in Winchester, VA?

    The Apple Blossom Festival in the spring is a big one, with parades, live music, and of course, lots of apples! The Shenandoah Valley Music Festival in the summer brings classical music to the area, and the Winchester Christmas Parade in December is a real treat.
  • What are the best places to stay with a pool in Winchester, VA?

  • What are the most convenient modes of transportation within Winchester, VA?

    Winchester is pretty walkable, especially in the Old Town area. If you're exploring further afield, you can hop on the local bus service, the WIN Transit. For longer trips, you can rent a car or use ride-sharing services like Uber or Lyft.
  • What are the best places to stay with a jacuzzi in Winchester, VA?

  • What outdoor activities and adventures are popular in and around Winchester, VA?

    The Shenandoah Valley is a nature lover's paradise! You can hike or bike the Appalachian Trail, explore the Shenandoah National Park, or go fishing or kayaking on the Shenandoah River. For a bit of adrenaline, there's also the Skydive Shenandoah drop zone nearby.
  • What are the best places to stay for families and kids in Winchester, VA?

    The best places to stay for families and kids in Winchester, VA are Hampton Inn Winchester, La Quinta By Wyndham Winchester and Tru By Hilton Winchester - Va.

  • What types of accommodations are available in Winchester, VA?

    You'll find a good range of accommodation options in Winchester, from budget-friendly hotels and motels to charming bed and breakfasts and even some luxury options. There are also some vacation rentals available if you're looking for something more spacious.
  • What are the best pet friendly places to stay in Winchester, VA?

  • When is the best time to visit Winchester, VA?

    Spring and autumn are lovely times to visit, with mild weather and vibrant colours. Summer can be hot and humid, but it's a great time for outdoor activities. Winter can be chilly, but it's a beautiful time to see the town decked out for the holidays.
  • What are the best places to stay with parking in Winchester, VA?

  • What local dishes and culinary experiences are a must-try in Winchester, VA?

    You have to try the local Shenandoah Valley apple cider donuts! They're a real treat. And don't miss the chance to sample some of the delicious local produce, like apples, peaches, and berries. The Winchester Farmers Market is a great place to find fresh, local ingredients.
  • In which part of Winchester, VA should you consider renting accommodation?

    The Old Town area is a great choice for a central location, close to the main attractions and restaurants. If you're looking for something quieter, the suburbs of Frederick County, like Stephens City, offer a more peaceful setting, but you'll need a car to get around.

Destinations nearby

Best Winchester, VA accommodations with a garden

Secret Gardens Carriage House - Winchester, VA
9.7 93 reviews
Winchester, VA
18/10 – 22/10
£157/nighttotal: £628 (4 )

Secret Gardens Carriage House

1 2
apartment , Winchester
This charming carriage house is located in Winchester, Virginia, a 5-minute drive from the Old Town Walking Mall and 30 minutes from the Blue Ridge Mountains. The property has received excellent ratings for location, cleanliness and overall experience.
This self-catering property can accommodate up to two guests and features a private screened-in porch, a fire pit, and a garden where you can pick fresh herbs. Guests can also enjoy the tranquil Zen gardens, observe local wildlife, and benefit from the expertise of the owners, Ramana and John.
Blue Peaks Signature Stay - Winchester, VA
Winchester, VA
18/10 – 22/10
£281/nighttotal: £1124 (4 )

Blue Peaks Signature Stay

3 2
apartment , Winchester
This three-bedroom, two-bathroom flat in Winchester offers prime downtown accommodation, situated just 100 metres from the Loudoun Street Walking Mall and within easy walking distance of restaurants, shops, and historic Winchester attractions.
This property, accommodating up to six guests, features air conditioning, Wi-Fi, and a fully equipped kitchen including a fridge, microwave, and dishwasher, making it suitable for couples, families, and business travellers seeking convenience and comfort.
Magnolia Wind 
3 Br 1 Ba Loft…
Walk To Downtown. - Winchester, VA
9.6 25 reviews
Winchester, VA
27/07 – 03/08
£109/nighttotal: £763 (7 )

Magnolia Wind 3 Br 1 Ba Loft… Walk To Downtown.

3 2
apartment , Winchester
This Winchester city centre apartment is located opposite the John Handley Library and a short 0.16 km walk from the Old Town Walking Mall.
The fully renovated loft sleeps seven guests in one bedroom with a king-size bed, a queen bed, two twin beds, and a sofa bed, offering free on-site parking, a fully equipped kitchen, and access to a sun porch.
Newly Repurposed Historic Home In Winchester Va! - Winchester, VA
9.8 135 reviews
Winchester, VA
06/07 – 07/07
£142/nightfor 1 night

Newly Repurposed Historic Home In Winchester Va!

1 2
apartment , Winchester
This charming apartment is situated just a short distance from Old Town Winchester's walking mall, offering easy access to the town's shops, restaurants, and cultural attractions. The apartment has consistently received excellent ratings for location, cleanliness, and overall user experience.
The apartment is a one-bedroom property that can comfortably accommodate two guests. It features a private patio, a modern kitchen, a washer and dryer, high-speed internet, and a 50-inch smart TV. Guests can enjoy the convenience of a pet-friendly environment, a garden, and the unique charm of a historic 1790s structure.

Best Winchester, VA accommodations with a kitchen

Peaceful Secret Gardens Tiny Home - Loft & Stairs  Lead To A Queen Size Bed - Winchester, VA
10 11 reviews
Winchester, VA
18/10 – 22/10
£138/nighttotal: £552 (4 )

Peaceful Secret Gardens Tiny Home - Loft & Stairs Lead To A Queen Size Bed

1 2
B&B , Winchester
This Winchester guesthouse is situated within 5km of the Kernstown Battlefield, Shenandoah University, and the Apple Blossom Mall, offering easy access to local attractions and parks such as Abram's Delight and Jim Barnett Park.
The smoke-free, one-bedroom guesthouse sleeps two, boasting a fridge, air conditioning, terrace, garden, fitness centre, parking, and on-site laundry facilities; housekeeping is available on request.
Cameron Grace Brand New Downtown 1 Br Loft - Winchester, VA
9.9 17 reviews
Winchester, VA
18/10 – 22/10
£161/nighttotal: £644 (4 )

Cameron Grace Brand New Downtown 1 Br Loft

1 2
apartment , Winchester
This apartment is situated in the heart of Winchester, just a short walk from the Old Town Winchester walking mall and a 5-minute drive from the Handley Library and the Museum of the Shenandoah Valley, offering easy access to the city's cultural attractions. This property has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment provides a comfortable and modern space for up to two guests, featuring a spacious living area, a well-equipped kitchen with a fridge, microwave oven, and dishwasher, and a full bathroom with a large shower. Guests can enjoy amenities such as private laundry facilities, air conditioning, free parking, and a peaceful retreat overlooking the treetops.
Treasure House - Winchester, VA
9.2 5 reviews
Winchester, VA
27/06 – 04/07
£150/nighttotal: £1050 (7 )

Treasure House

1 2
apartment , Winchester
This three-bedroom Winchester house, sleeping seven, is located a short 3.2-kilometre drive from Winchester city centre, offering easy access to restaurants and the Winchester Shopping Centre.
The property boasts a fully equipped eat-in kitchen, designated workspace, high-speed internet, ample parking, and is pet-friendly (dogs welcome), providing a comfortable stay for families or groups visiting Winchester.
Cleveland Park Awesome Winchester 2 Br 1st Fl  Apt. Walk To Everything! - Winchester, VA
10 1 review
Winchester, VA
27/07 – 03/08
£97/nighttotal: £679 (7 )

Cleveland Park Awesome Winchester 2 Br 1st Fl Apt. Walk To Everything!

2 2
apartment , Winchester
This ground-floor flat is situated in the Winchester Historic District, offering convenient access to downtown shops, the walking mall, Bright Box Theater, and the Old Court House Civil War Museum, all within a 500-meter walk.
This 2-bedroom, 1-bathroom apartment accommodates up to 5 guests and features air conditioning, parking, and a kitchen with a microwave oven, providing easy access to Abrams Creek Wetlands Preserve and Red Bud Run.
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