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.
9.6 78 reviews
Winchester, VA
01/10 – 09/10
A$150/nighttotal: A$1200 (8 )
Rosamond Downtown Studio Apt W/free Parking
1 2
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.
9.7 76 reviews
Winchester, VA
01/10 – 09/10
A$167/nighttotal: A$1336 (8 )
The Stock Exchange Downtown Hip Studio Apt
1 2
apartment , Winchester
This Winchester city centre apartment is situated a 1.5-block walk from the Winchester City Mill, offering easy access to the Saturday Farmers' Market and shops. The self-contained studio flat, sleeping up to two guests, features a full-size futon, kitchen with fridge and microwave, air conditioning, on-site parking, and a large flat-screen TV; coin-operated laundry facilities are available on the ground floor.
9.5 116 reviews
Winchester, VA
13/10 – 23/10
A$184/nighttotal: A$1840 (10 )
The Blue Door Steps From Handley Library
1 1
apartment , Winchester
This Winchester city centre studio apartment is conveniently located near the Handley Library, two blocks from the pedestrian shopping area, and within an 8km drive of Shenandoah University and Winchester Medical Centre. The self-catering apartment sleeps two, boasts a full kitchen with fridge and microwave, a 32” flat-screen TV with Roku, two complimentary parking spaces, and access to on-site laundry facilities; nearby attractions include the Skyline Drive (a 48km drive) and Washington, D.C. (a 240km drive).
10 4 reviews
Winchester, VA
28/06 – 05/07
A$271/nighttotal: A$1897 (7 )
Cozy & Charming Downtown Apartment
1 2
apartment , Winchester
This one-bedroom flat is in historic Winchester, Virginia, offering a prime downtown location within 100 metres of Handley Library and a short drive to Bear's Den for scenic hikes. This apartment accommodates two guests and features air conditioning, free on-site parking with an assigned spot, a fully equipped kitchen with a fridge, freezer, and microwave, and a dedicated desk area for professionals.
9.6 25 reviews
Winchester, VA
13/10 – 23/10
A$241/nighttotal: A$2410 (10 )
Magnolia Wind
3 Br 1 Ba Loft…
Walk To Downtown.
3 1
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.
9.7 53 reviews
Winchester, VA
13/10 – 23/10
A$254/nighttotal: A$2540 (10 )
The Queen Of Winchester - Three Bedroom Apartment
1 1
apartment , Winchester
This three-bedroom Winchester apartment, named 'Queen of Winchester', enjoys a central location offering easy access to Winchester's historic city centre and its numerous attractions, including Winchester Cathedral. The luxurious flat features a private terrace, parking, air conditioning, and internet access, comfortably sleeping four guests.
9.4 75 reviews
Winchester, VA
13/10 – 23/10
A$145/nighttotal: A$1450 (10 )
Immerse Yourself In Old Town #3 We'll Pay Parking!
1 1
apartment , Winchester
This one-bedroom loft apartment is situated in Old Town Winchester, just off the Old Town Mall, within walking distance of shops, restaurants, and the Winchester Medical Center (5 minutes away). The apartment enjoys excellent user, location, and cleanliness ratings. The apartment, which can accommodate up to four guests, is equipped with a fridge, freezer, microwave oven, and air conditioning. Guests can enjoy a unique and comfortable stay in a clean and stylish apartment, with added security features like motion detectors and security lighting.
9.8 24 reviews
Winchester, VA
01/10 – 09/10
A$222/nighttotal: A$1776 (8 )
Two Bdrm. Flat W/ Patio Terrace
1 2
apartment , Winchester
This Old Town Winchester flat is ideally located less than 0.16 km from Winchester's historic sites, the Discovery Museum, and the Old Town walking mall, offering easy access to local attractions. The two-bedroom, two-bathroom self-catering apartment, sleeping up to four guests, features a fully equipped kitchenette, air conditioning, and a private patio terrace.
9.8 298 reviews
Winchester, VA
13/10 – 23/10
A$214/nighttotal: A$2140 (10 )
Modern Elegance In Historic Old Town Winchester
1 1
house , Winchester
This charming one-bedroom house is situated just 1.6 kilometres from Winchester's historic Old Town, within walking distance of the pedestrian mall, The Brightbox Theatre, and The Shenandoah Discovery Museum. The property offers a spacious modern kitchen, a comfortable living space, and a private garden, making it ideal for families or small groups visiting Winchester.
9.5 103 reviews
Winchester, VA
02/09 – 06/09
A$312/nighttotal: A$1248 (4 )
Cleveland Park Bright 2br Apt Blocks From Downtown
1 4
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.
9.7 93 reviews
Winchester, VA
01/10 – 09/10
A$171/nighttotal: A$1368 (8 )
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.
Winchester, VA: Best family friendly accommodations
Among the 114 accommodations in the area, here is the list of the 4 best family friendly ones
9.7 46 reviews
Winchester, VA
01/10 – 09/10
A$172/nighttotal: A$1376 (8 )
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.
10 217 reviews
Winchester, VA
13/10 – 23/10
A$226/nighttotal: A$2260 (10 )
Cameron Charmer Pristine W/double Master Suites
1 1
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.
8.8 9 reviews
Winchester, VA
28/06 – 05/07
A$395/nighttotal: A$2765 (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.
8.8 5 reviews
Winchester, VA
13/10 – 23/10
A$261/nighttotal: A$2610 (10 )
Dreamweaver 1br 1ba Just Two Blocks From The Downtown Walking Mall
1 1
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.
Winchester, VA: Best accommodations with a pool
Among the 114 accommodations in the area, here is the list of the 1 best ones with a pool
10 10 reviews
Winchester, VA
02/09 – 06/09
A$881/nighttotal: A$3524 (4 )
Winchester Farm
1 4
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 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?
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?
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?
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.
Destinations nearby
Best Winchester, VA accommodations with a garden
10 11 reviews
Winchester, VA
01/10 – 09/10
A$148/nighttotal: A$1184 (8 )
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.
9.8 136 reviews
Winchester, VA
13/10 – 23/10
A$230/nighttotal: A$2300 (10 )
Scarborough Fair Walk To Downtown Two Story Apt
1 1
apartment , Winchester
This Winchester apartment is ideally located in the heart of the city, just a short walk from the Handley Library, the walking mall, and the Scarborough Fair, making it easy to explore the area's historical attractions and vibrant atmosphere. It has received excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay. This spacious home offers three bedrooms and can comfortably accommodate up to eight guests. It features a fully equipped kitchen, air conditioning, a garden, and multiple porches for relaxing, as well as free parking and pet-friendly policies.
8.0 7 reviews
Winchester, VA
31/10 – 01/11
A$570/nightfor 1 night
2 Bedroom Condo In Stephens City
1 2
apartment , Stephens City
This Stephens City apartment, situated in the Shenandoah Valley, is approximately 16km from Winchester, Virginia, and 160km from Washington, D.C. and Luray Caverns. The two-bedroom, two-bathroom property sleeps four guests and includes amenities such as Wi-Fi, parking, and air conditioning; nearby attractions include a lake, nature trail, and local library.
9.8 404 reviews
Winchester, VA
01/10 – 09/10
A$329/nighttotal: A$2632 (8 )
Old Town 1920s Gas Station With Hot Tub
1 2
apartment , Winchester
This stylish flat is located in Old Town Winchester, just a short walk from the downtown walking mall, breweries, and the Pizzoco Pizza parlor. The apartment has received excellent ratings for its location, cleanliness, and overall experience. The flat is a one-bedroom property with one bathroom, comfortably accommodating two guests. The apartment features a fully equipped kitchen, a private parking space with an EV charging station, and a range of modern amenities including a smart TV, high-speed Wi-Fi, and a washer/dryer.
Best Winchester, VA accommodations with a kitchen
9.6 297 reviews
Winchester, VA
01/10 – 09/10
A$197/nighttotal: A$1576 (8 )
Pretty Little Apt By The Train Ii
1 2
apartment , Winchester
This charming studio apartment is situated above a downtown shop in Winchester, Virginia, just a short walk from the Walking Mall and within easy reach of Shenandoah University and Winchester Medical Center. The studio has received excellent ratings for its location, cleanliness, and overall guest experience. The studio is a comfortable and well-equipped one-bedroom apartment with a queen-sized bed and can accommodate up to two guests. Amenities include a kitchen with a fridge and microwave, air conditioning, a garden, parking, and a record player with a selection of vinyl records.
9.0 16 reviews
Winchester, VA
01/10 – 09/10
A$272/nighttotal: A$2176 (8 )
Nostalgia Lane In The Heart Of The City
3 2
apartment , Winchester
This Winchester Old Town flat offers prime accommodation, situated a short walk from the Bright Box Theatre and Old Courthouse Civil War Museum, with the Shenandoah Valley Discovery Museum and George Washington's Office less than 0.8km away. The 102 square metre property sleeps six guests and includes three bedrooms, one bathroom, a dryer, TV, and is well-equipped for a comfortable stay.
9.5 126 reviews
Winchester, VA
13/10 – 23/10
A$222/nighttotal: A$2220 (10 )
Yellow Submarine Trendy Basement Apt W/courtyard
3 1
apartment , Winchester
This two-bedroom flat is situated in the heart of Winchester, just a stone's throw from the Handley Library and the bustling walking mall. The property has received excellent ratings for location, cleanliness, and overall user experience. The apartment comfortably accommodates up to four guests and features a queen-sized bed in one bedroom and a double futon/couch in the other. Guests can enjoy amenities such as air conditioning, a garden, parking, and a shared laundry room, making it ideal for a relaxing and convenient stay.
8.0 2 reviews
Winchester, VA
01/10 – 09/10
A$153/nighttotal: A$1224 (8 )
Rosamond Nice Downtown Studio Apt
1 2
studio , Winchester
This Winchester studio apartment is situated in the heart of the city centre, just a short walk from the pedestrianized shopping area and the historic Old Court House Civil War Museum. The self-catering studio offers a comfortable queen-sized bed, a fully equipped kitchen, and a private bathroom, making it ideal for a couple's getaway.