Search Winchester, VA accommodations

189 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Winchester, VA accommodation
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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.

Magnolia Wind 
3 Br 1 Ba Loft
Walk To Downtown. - Winchester, VA
9.6 26 reviews

Magnolia Wind 3 Br 1 Ba Loft Walk To Downtown.

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.
Cleveland Park Bright 2br Apt Blocks From Downtown - Winchester, VA
9.5 107 reviews

Cleveland Park Bright 2br Apt Blocks From Downtown

apartment, Winchester
This two-bedroom flat is located in Cleveland Park, just 0.2km from the walking mall in Winchester's downtown area, making it ideal for exploring the city's shops, restaurants, and cultural attractions. It has consistently received excellent ratings for location, cleanliness, and overall experience.
The ground floor flat sleeps up to five guests and features a fully equipped kitchen with a fridge and microwave, air conditioning, and designated parking. Guests can enjoy the spacious living room with a sofa bed, as well as the convenience of internet access and pet-friendly policies.
Old Town Loft In Highly Desirable Area Downtown - Winchester, VA
10 258 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.
Magnolia Winds 3-bedroom Apartment In Charming Winchester With Cool Ac - Winchester, VA
10 7 reviews

Magnolia Winds 3-bedroom Apartment In Charming Winchester With Cool Ac

apartment, Winchester
This three-bedroom flat is situated in Winchester's Old Town, offering proximity to Handley Regional Library and Stonewall Jackson's Headquarters, with Jim Barnett Park and Frederick Douglass Park a short 3.2-kilometre drive away.
This property provides Wi-Fi, air conditioning, a dryer, and ironing facilities, alongside essential toiletries, making it a convenient base for exploring Winchester's historical sites and natural reserves.

Best Winchester, VA accommodations with parking

Wonderclock House Downtown Vintage Duplex W/ Porches, Steps To Handley Library - Winchester, VA
9.0 10 reviews

Wonderclock House Downtown Vintage Duplex W/ Porches, Steps To Handley Library

apartment, Winchester
This Old Town Winchester flat is ideally located less than a kilometre from the Handley Regional Library, the Old Court House Civil War Museum, and the Bright Box Theatre, offering easy access to Winchester's historical attractions.
The 116-square-metre property boasts three bedrooms, two bathrooms, and accommodates up to six guests, including amenities such as Wi-Fi, air conditioning, and a television.
Charming 4-bedroom House On Beautiful Farm In Clear Brook With Lovely Views - Winchester, VA
10 19 reviews

Charming 4-bedroom House On Beautiful Farm In Clear Brook With Lovely Views

apartment, Winchester
This Clear Brook farmhouse, situated in Winchester, Virginia, offers a serene escape near Rutherford Crossing and Northside Station shopping centres, providing easy access to outdoor pursuits such as Red Bud Run and Abrams Creek Wetlands Preserve.
The 4-bedroom property sleeps 8 guests, boasting a king-size bed, three queen-size beds, and a full-size bed, along with a fully equipped kitchen (fridge, microwave, dishwasher), a fitness centre, parking, and a large deck ideal for sunset viewing, plus access to nearby attractions including Nalls Farm Market and Frederick County Fairgrounds.
Whole 3-bedroom House Walkable To Downtown. - Winchester, VA
9.9 38 reviews

Whole 3-bedroom House Walkable To Downtown.

apartment, Winchester
Nancy's Nook, a three-bedroom house in a quiet Winchester neighbourhood, is within easy walking distance of the Old Town's Walking Mall and farmers market.
This single-storey property sleeps six, boasts two sitting rooms, a sunroom, high-speed internet, and off-street parking for two cars, plus nearby amenities including Walmart, Target, and Martins Grocery.
Cozy English Basement Apt Quiet But Close To Downtown - Winchester, VA
9.6 8 reviews

Cozy English Basement Apt Quiet But Close To Downtown

apartment, Winchester
This Winchester apartment is conveniently located within 1.6km of the Winchester Little Theatre, George Washington's Office, and the Shenandoah Valley Discovery Museum.
The one-bedroom, one-bathroom flat sleeps two guests and includes in-unit laundry facilities, free Wi-Fi, and essential amenities such as a TV, hairdryer, and iron; nearby attractions include the Bright Box Theatre and the Old Court House Civil War Museum.

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.

191 M² House ∙ 3 Bedrooms ∙ 6 Guests - Winchester, VA
No reviews

191 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Winchester
Holiday house for 6 guests. You will be located in Winchester.
Facilities and services: a dish washer, free parking and a terrace. Take advantage of the garden in this house!
Dreamweaver  1br 1ba Just Two Blocks From The Downtown Walking Mall - Winchester, VA
8.8 5 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
10 221 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.
Springdale Mill Farmhouse With Spa House - Winchester, VA
9.7 91 reviews

Springdale Mill Farmhouse With Spa House

apartment, Stephens City
This farmhouse, dating back to 1731, is located just a short distance from Stephens City, Virginia, offering a tranquil setting near the Opequon Creek. The property enjoys excellent ratings for location, cleanliness, and overall user experience.
This historic home offers four bedrooms and two bathrooms, comfortably accommodating up to eight guests. Enjoy modern amenities like high-speed internet, a well-equipped kitchen, a Jacuzzi, a sauna, and a private garden, making it perfect for a relaxing getaway.

Best Winchester, VA accommodations with a garden

Cameron Street Retreat: King Bed & Office Downtown - Winchester, VA
9.8 26 reviews

Cameron Street Retreat: King Bed & Office Downtown

apartment, Winchester
This Winchester city centre flat, a short drive (approx. 80km) from Washington, D.C. and 64km from Skyline Drive and Harpers Ferry, is situated in a historic district.
The 1-bedroom apartment, sleeping up to two guests, offers a king-size bed, queen-size sofa bed, dedicated workspace, in-unit laundry, and complimentary off-street parking, plus starter supplies.
Historic District Charm On Cameron Street - Winchester, VA
9.8 175 reviews

Historic District Charm On Cameron Street

apartment, Winchester
This Winchester apartment, situated in the historic district, is within walking distance of the Winchester High Street and close to Shenandoah University and the Museum of the Shenandoah Valley.
The three-bedroom property boasts a full kitchen, dining room, family room, dedicated workspace, private deck, and half-court basketball court, comfortably accommodating up to four guests (with additional charges for more than four).
Merrimans Meadow - Winchester, VA
10 85 reviews

Merrimans Meadow

apartment, Winchester
This English basement studio is located in Winchester, Virginia, just 0.8km from Winchester Medical Centre and 1.6km from Winchester's town centre.
The self-contained studio apartment, with a private entrance, sleeps two guests and features a fully equipped kitchen, a private garden, and free parking.
Merrimans Hope 5br Spacious & Stunning - Winchester, VA
No reviews

Merrimans Hope 5br Spacious & Stunning

apartment, Winchester
This five-bedroom, two-bathroom holiday home in Winchester offers convenient access to nature and culture, located a 2-minute drive from Abrams Creek Wetlands Preserve and the Museum of the Shenandoah Valley.
This spacious 539 square meter property accommodates up to 10 guests and features Wi-Fi, air conditioning, a garden, and on-site parking.

Best Winchester, VA accommodations with a kitchen

Downtowner - Winchester, VA
9.9 351 reviews

Downtowner

apartment, Winchester
Immerse Yourself In Old Town #3 We'll Pay Parking! - Winchester, VA
9.4 75 reviews

Immerse Yourself In Old Town #3 We'll Pay Parking!

apartment, Winchester
3 Bedroom Upper Unit, Quiet Area Close To Town - Winchester, VA
9.7 7 reviews

3 Bedroom Upper Unit, Quiet Area Close To Town

apartment, Winchester
Cameron Loft 2 Story Studio With 1.5 Bath Downtown - Winchester, VA
10 16 reviews

Cameron Loft 2 Story Studio With 1.5 Bath Downtown

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.

Sunrise/sunset Views - Winchester, VA
10 9 reviews

Sunrise/sunset Views

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.

Morocco Loft 2br Overlooking The City - Winchester, VA
9.4 61 reviews

Morocco Loft 2br Overlooking The City

apartment, Winchester
Pets? Yes!  Hot Tub  Fire Pit  Fast Wi-fi - Winchester, VA
9.9 187 reviews

Pets? Yes! Hot Tub Fire Pit Fast Wi-fi

cottage, Boyce
The Road Less Traveled 1 Bedroom Near Walking Mall - Winchester, VA
9.4 58 reviews

The Road Less Traveled 1 Bedroom Near Walking Mall

apartment, Winchester
Wonderclock House Steps From Handley Library - Winchester, VA
9.5 182 reviews

Wonderclock House Steps From Handley Library

apartment, Winchester
©2026 cozycozy.com