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Winchester, VA accommodation
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189 Best accommodations in Winchester, VA

Find City Centre Accommodations in Winchester, VA, United States

Stay within easy walking distance of the best local bakeries, markets, and squares from central accommodation in Winchester, VA, United States.

Old Town Loft In Highly Desirable Area Downtown - Winchester, VA
10 264 reviews

Old Town Loft In Highly Desirable Area Downtown

apartment, Winchester
This charming one-bedroom flat in Winchester is ideally situated in the town centre, just a short walk from the Old Town mall, farmers' market, and a wide range of restaurants, cafes, and bars. The accommodation has received excellent ratings for its cleanliness, location, and overall experience.
The flat has a well-equipped kitchen, a comfortable living area, and a modern bathroom, making it suitable for couples or solo travellers. Guests can enjoy the historic charm of the building, the modern amenities, and the convenient location for exploring the town's attractions and enjoying its vibrant atmosphere.
Rosamond Downtown Studio Apt W/free Parking - Winchester, VA
9.6 80 reviews

Rosamond Downtown Studio Apt W/free Parking

apartment, Winchester
This studio apartment is located just two blocks from the bustling downtown walking mall in Winchester, Virginia, offering easy access to shops, restaurants, and entertainment. It boasts excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The studio comfortably sleeps two guests and features a designated workspace and a comfortable full-sized futon bed. Amenities include a flat-screen TV with Roku, a fully equipped kitchen, a bathroom with a tub, and free parking.
Cameron Loft 2 Story Studio With 1.5 Bath Downtown - Winchester, VA
10 17 reviews

Cameron Loft 2 Story Studio With 1.5 Bath Downtown

apartment, Winchester
The Cameron Loft, a two-level studio apartment in Winchester city centre, offers convenient access to downtown attractions.
This self-contained apartment sleeps two, features a fully equipped kitchen, in-unit laundry, complimentary parking, and fast WiFi; starter supplies are provided.
Morocco Loft 2br Overlooking City Walking Mall - Winchester, VA
10 3 reviews

Morocco Loft 2br Overlooking City Walking Mall

apartment, Winchester
This Old Town Winchester flat is ideally situated near the Bright Box Theatre and the Old Court House Civil War Museum, within a 0.8km radius of the Shenandoah Valley Discovery Museum and George Washington's Office.
This 116 square metre apartment, sleeping up to five guests, boasts two bedrooms, one bathroom, in-unit laundry facilities, and essential amenities such as a hairdryer and iron; its central location provides easy access to Winchester's historical sites, shops, and restaurants.

Best Winchester, VA accommodations with parking

3 Bedroom Upper Unit, Quiet Area Close To Town - Winchester, VA
9.9 14 reviews

3 Bedroom Upper Unit, Quiet Area Close To Town

apartment, Winchester
This three-bedroom flat is situated in a peaceful cul-de-sac, less than 5 kilometres from Winchester's town centre and a 5-minute drive from Shenandoah University, offering a private setting on a double lot bordering parkland. The property accommodates up to eight guests and features a fully equipped kitchen, air conditioning, and an expansive wrap-around porch for outdoor enjoyment.
The Cozy Brick Cottage On Opequon Ave - Winchester, VA
8.0 1 review

The Cozy Brick Cottage On Opequon Ave

apartment, Winchester
This three-bedroom, one-bathroom flat is located in Winchester, just 5 minutes from Old Town and 20 minutes from Shenandoah hikes and wineries.
This pet-friendly accommodation offers parking, air conditioning, and a fully equipped kitchen, with a guest capacity of six.
Cameron Charmer Pristine Downtown Apt With Double Master Suites - Winchester, VA
9.6 9 reviews

Cameron Charmer Pristine Downtown Apt With Double Master Suites

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.
Sweet Dreams' Cozy Cottage In Downtown Winchester - Winchester, VA
10 1 review

Sweet Dreams' Cozy Cottage In Downtown Winchester

cottage, Winchester
This detached house in Winchester is located within easy walking distance of the Patsy Cline Historic House and the Shenandoah Valley Discovery Museum, approximately 800 meters away.
This detached house accommodates two guests and features one bedroom, one bathroom, a kitchenette with a fridge and microwave, air conditioning, WiFi, and a garden with outdoor furniture, with parking also available.

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 definitely want to check out the Old Town Winchester, with its charming shops and restaurants, and the George Washington's Headquarters Museum. The Winchester-Frederick County Historical Society Museum is another great option to learn about the area's past. If you're into the Civil War, the National Confederate Memorial is a must-visit. The Winchester Museum of the Shenandoah Valley is a great place to learn about the area's natural history and art.
  • What are the best accommodations in Winchester, VA?

    Among the accommodations 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?

    Winchester has a vibrant calendar of events! You'll want to check out the Apple Blossom Festival in the spring, with its parades and live music. The Shenandoah Valley Music Festival in the summer brings classical music to the area. And in the fall, the Winchester Fall Festival is a great way to experience local crafts and food.
  • What are the best accommodations with a pool in Winchester, VA?

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

    Winchester is fairly compact, so walking is a great option, especially in Old Town. You can also use the Winchester Area Transit (WAT) bus system, which has routes throughout the city. If you're coming from further afield, the Winchester Regional Airport is a good option, although it only has a few flights each day.
  • What are the best accommodations with a jacuzzi in Winchester, VA?

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

    Winchester is in the heart of the Shenandoah Valley, so there are plenty of outdoor activities. You can hike or bike the Appalachian Trail, which passes through the area. The Shenandoah National Park, just a short drive away, offers stunning scenery and hiking trails. For something a bit more relaxed, you can enjoy a picnic at Jim Barnett Park or take a stroll along the North Fork Shenandoah River.
  • What are the best accommodations for families and kids in Winchester, VA?

    The best accommodations 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?

    Winchester has a good range of accommodation options. There are several hotels in the city centre, as well as motels along the main roads. If you're looking for something more unique, there are also bed and breakfasts and vacation rentals available.
  • What are the best pet friendly accommodations in Winchester, VA?

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

    The best time to visit Winchester depends on what you're interested in. Spring is lovely for the Apple Blossom Festival and mild weather. Summer is great for outdoor activities, and autumn brings beautiful fall foliage. Winter can be cold, but it's a great time to enjoy the city's festive atmosphere.
  • What are the best accommodations 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 cuisine! The Winchester Farmers Market is a great place to sample local produce and artisan goods. Be sure to try the Shenandoah Valley apple pie, a local favourite. And don't forget to check out the Winchester Brew Works, which has a wide selection of craft beers.
  • In which part of Winchester, VA should you consider renting accommodation?

    Old Town Winchester is the heart of the city, with lots of shops, restaurants, and historic attractions. It's a great place to stay if you want to be in the thick of things. If you're looking for something more affordable, there are also hotels and motels on the outskirts of town.

Popular destinations

Discover Premium Family-Friendly Accommodations in Winchester, VA, United States

Give the family plenty of room to stretch out with local parks and sights nearby at family accommodation in Winchester, VA, United States.

New Charming 3-bedroom  2 Full Bath And 1 Half Bedrooms Single Family  House - Winchester, VA
8.6 10 reviews

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

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.
Downtowner - Winchester, VA
9.9 358 reviews

Downtowner

apartment, Winchester
This charming apartment is located in a quiet residential area of Winchester's Historic District, just a short walk (less than 1 km) from the bustling downtown pedestrian mall. It has consistently received excellent ratings for location, cleanliness and overall experience.
The apartment sleeps up to four guests and features a fully equipped kitchenette, a relaxing front porch, and in-house laundry facilities. Guests can enjoy a range of amenities, including free Wi-Fi, air conditioning, and private parking.
Dreamweaver  1br 1ba Just Two Blocks From The Downtown Walking Mall - Winchester, VA
8.4 6 reviews

Dreamweaver 1br 1ba Just Two Blocks From The Downtown Walking Mall

apartment, Winchester
This Winchester Historic District flat offers convenient access, within 1.6km, to Stonewall Jackson's Headquarters, the Handley Regional Library, and the Old Court House Civil War Museum.
The self-catering apartment sleeps two, features a fully equipped kitchen, free Wi-Fi, and on-request housekeeping, and is close to Bright Box Theatre and Mount Hebron Cemetery.
Cameron Charmer Pristine W/double Master Suites - Winchester, VA
10 224 reviews

Cameron Charmer Pristine W/double Master Suites

apartment, Winchester
This recently renovated 1930s house, located in Winchester, Virginia's up-and-coming downtown area, is a 5-minute walk from the Old Town walking mall and within easy reach of Shenandoah University (8 km), Winchester Medical Center (16 km), and Skyline Drive (48 km).
This 150 sq m property offers two master suites each with an en-suite bathroom and walk-in closets, a dine-in kitchen with fridge, microwave, and dishwasher, accommodating up to four guests and boasting a garden and parking.

Best Winchester, VA accommodations with a garden

Peaceful Secret Gardens Tiny Home - A Space To Relax And Get Away From It All. - Winchester, VA
10 12 reviews

Peaceful Secret Gardens Tiny Home - A Space To Relax And Get Away From It All.

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.
Large Historic Stone Home In The Heart Of Old Town - Winchester, VA
10 78 reviews

Large Historic Stone Home In The Heart Of Old Town

house, Winchester
This charming four-bedroom house is situated in Old Town Winchester, just a short walk from the bustling walking mall, popular restaurants, and shops. It has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
The house provides ample space for a large group with its multiple living areas and dedicated laundry room. Guests can enjoy modern amenities such as stainless steel appliances, granite countertops, and a multi-zone heating and cooling system, all while appreciating the historic charm of the 1800s home.
Merrimans Hope 
5br Spacious & Stunning On 2 +Acre - Winchester, VA
10 7 reviews

Merrimans Hope 5br Spacious & Stunning On 2 +Acre

apartment, Winchester
Merriman's Hope is a five-bedroom, two-bathroom detached house situated on a secluded 12,000 square metre property, offering a peaceful country escape just 5 minutes by car from Winchester's town centre attractions.
This substantial property provides accommodation for up to 10 guests, featuring a gourmet kitchen with a large pantry, a ground-floor master suite, multiple outdoor living spaces, a hot tub, and a formal living room with an upright piano.
Old Town Modern Twist! Rock N Roll Fun W/parking! - Winchester, VA
9.9 208 reviews

Old Town Modern Twist! Rock N Roll Fun W/parking!

apartment, Winchester
This charming flat is situated in the heart of Winchester, just a short walk from the city's bustling coffee shops, restaurants and boutiques, as well as the historic Shenandoah Valley Museum. It has received excellent ratings for location, cleanliness and overall experience.
The apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. It includes a fully equipped kitchen, a dedicated workspace, a private parking space, a washer and dryer, and air conditioning for a comfortable stay.

Best Winchester, VA accommodations with a kitchen

Very Charming & Spacious 2 Bedrm - Winchester, VA
8.0 1 review

Very Charming & Spacious 2 Bedrm

apartment, Winchester
Nostalgia Lane 3 Br In The Heart Of The City - Winchester, VA
9.7 241 reviews

Nostalgia Lane 3 Br In The Heart Of The City

apartment, Winchester
Cleveland Park Awesome Winchester 2 Br 1st Fl  Apt. Walk To Everything! - Winchester, VA
10 2 reviews

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

apartment, Winchester
Downtown Fun! Personal Mid Century 2bd Apartment! - Winchester, VA
9.8 278 reviews

Downtown Fun! Personal Mid Century 2bd Apartment!

apartment, Winchester

Find the Best Accommodations with a Swimming Pool in Winchester, VA, United States

Make a splash under the summer sun or swim peaceful morning laps at accommodation with a pool in Winchester, VA, United States.

Winchester Farm - Winchester, VA
10 13 reviews

Winchester Farm

apartment, Winchester

The Best High-End Accommodation in Winchester, VA, United States

Experience high-end hospitality and immersive local charm at premium accommodation in a historic setting in Winchester, VA, United States.

Morocco Loft 2br Overlooking The City - Winchester, VA
9.5 64 reviews

Morocco Loft 2br Overlooking The City

apartment, Winchester

Leading Dog-Friendly Accommodations in Winchester, VA, United States

Let your dog stretch their legs and explore a new area alongside you at pet-friendly accommodation in Winchester, VA, United States.

Newly Repurposed Historic Home In Winchester Va! - Winchester, VA
9.8 144 reviews

Newly Repurposed Historic Home In Winchester Va!

apartment, Winchester
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