Search Winchester, VA accommodations

114 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

114 Best accommodations in Winchester, VA

Winchester, VA: Best family friendly accommodations

Among the 114 accommodations in the area, here is the list of the 4 best family friendly ones

Dreamweaver
Bright 1br  
2 Blocks To Walking Mall - Winchester, VA
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.
Cameron Charmer Pristine W/double Master Suites - Winchester, VA
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.
New Charming 3-bedroom  2 Full Bath And 1 Half Bedrooms Single Family  House - Winchester, VA
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.
Dreamweaver  1br 1ba Just Two Blocks From The Downtown Walking Mall - Winchester, VA
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

Winchester Farm - Winchester, VA
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?

    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.

Destinations nearby

Best Winchester, VA accommodations with a garden

Peaceful Secret Gardens Tiny Home - Loft & Stairs  Lead To A Queen Size Bed - Winchester, VA
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.
Scarborough Fair Walk To Downtown Two Story Apt - Winchester, VA
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.
2 Bedroom Condo In Stephens City - Winchester, VA
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.
Old Town 1920s Gas Station With Hot Tub - Winchester, VA
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

Pretty Little Apt By The Train Ii - Winchester, VA
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.
Nostalgia Lane In The Heart Of The City - Winchester, VA
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.
Yellow Submarine Trendy Basement Apt W/courtyard - Winchester, VA
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.
Rosamond Nice Downtown Studio Apt - Winchester, VA
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.
©2026 cozycozy.com