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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.

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

Wonderclock House Steps From Handley Library

apartment, Winchester
This Winchester city centre duplex is situated a short walk from the Handley Library and the pedestrian mall, offering easy access to the Museum of the Shenandoah Valley and Discovery Museum (less than 0.8km away).
The three-bedroom, one-bathroom apartment sleeps six, features a fairytale theme, a garden, free on-site parking, and is close to restaurants, cafes such as the Expresso Bar, and entertainment venues including the George Washington Hotel's Half Note Lounge and Bright Box.
Cameron Corner: King Bed & Office Downtown - Winchester, VA
10 20 reviews

Cameron Corner: King Bed & Office Downtown

apartment, Winchester
This modern one-bedroom apartment is situated in the heart of Winchester, within walking distance of the High Street, restaurants, and the iconic Winchester Cathedral.
The apartment offers free parking, a fully equipped kitchen with dishwasher, laundry facilities, and can comfortably accommodate up to four guests.
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.
The Stock Exchange Downtown Hip Studio Apt - Winchester, VA
9.7 78 reviews

The Stock Exchange Downtown Hip Studio Apt

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.

Best Winchester, VA accommodations with parking

Charming Farmhouse - Winchester, VA
No reviews

Charming Farmhouse

apartment, Winchester
This two-bedroom maisonette is located in Winchester, offering a peaceful countryside setting with immediate access to the historic downtown, just a few kilometres away.
This pet-friendly property accommodates up to four guests and features a kitchen, air conditioning, internet, and parking, with a firepit area for evening use and proximity to the Shenandoah Valley for outdoor pursuits.
Cleveland Park Awesome Winchester 2 Br 1st Fl  Apt. Walk To Everything! - Winchester, VA
10 1 review

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

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.
Scarborough Fair Walk To Downtown Two Story Apt - Winchester, VA
9.8 7 reviews

Scarborough Fair Walk To Downtown Two Story Apt

apartment, Winchester
This Old Town Winchester flat offers a convenient location, less than 1 km from the Handley Regional Library, Old Courthouse Civil War Museum, and Bright Box Theatre.
The 209 square metre self-catering property sleeps up to 10 guests and includes three bedrooms, one bathroom, in-unit laundry, a fireplace, and a Smart TV, plus parking.
Very Charming & Spacious 2 Bedrm - Winchester, VA
8.0 1 review

Very Charming & Spacious 2 Bedrm

apartment, Winchester
This Winchester apartment is situated near the Apple Blossom Mall (8 km) and Patsy Cline's childhood home (9.6 km), offering easy access to the Shenandoah River and Mackintosh Fruit Farm.
The two-bedroom, one-bathroom flat provides internet, air conditioning, and in-unit amenities including towels and hairdryer; nearby attractions include the Shenandoah Valley Museum and Nalls Farm Market.

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.

Peaceful Family Retreat In The Heart Of Winchester - Winchester, VA
10 76 reviews

Peaceful Family Retreat In The Heart Of Winchester

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.
City Charmer Near Historic Oldtown Winchester. - Winchester, VA
9.9 351 reviews

City Charmer Near Historic Oldtown Winchester.

apartment, Winchester
This Winchester holiday home is located just 2km from the Handley Regional Library and Old Court House Civil War Museum, offering easy access to cultural and historical attractions, and is situated near a park and cemetery, providing a tranquil setting. The property has received excellent ratings for location, cleanliness, and overall user experience.
This 74 square metre property comfortably sleeps four guests in its two bedrooms and one bathroom. Guests can enjoy a fully equipped kitchen, free WiFi, a DVD player, a terrace or balcony, a garden, and parking.
191 M² House ∙ 3 Bedrooms ∙ 6 Guests - Winchester, VA
No reviews

191 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Winchester
House rental for up to 6 people. You will be located in Winchester.
Facilities and services: a washing machine, a dish washer and air conditioning. Take advantage of the terrace in this house in Winchester.
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.

Best Winchester, VA accommodations with a garden

Modern Mid-century Townhome W Deck Near Festivals - Winchester, VA
9.0 10 reviews

Modern Mid-century Townhome W Deck Near Festivals

house, Winchester
This modern townhome in Winchester, VA, is located 5 kilometres from Abrams Creek Wetlands Preserve and 10 kilometres from Old Town Winchester and James Charles Winery & Vineyard.
This 3-bedroom, 3-bathroom property accommodates up to 5 guests and features a fully equipped kitchen, air conditioning, high-speed internet ideal for remote work, and a lower-level hangout space with a Smart TV.
3 Bedroom Upper Unit, Quiet Area Close To Town - Winchester, VA
9.8 12 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.
Yellow Submarine Trendy Basement Apt W/courtyard - Winchester, VA
9.5 130 reviews

Yellow Submarine Trendy Basement Apt W/courtyard

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.
Secret Gardens Tiny House - Winchester, VA
10 50 reviews

Secret Gardens Tiny House

house, Winchester
This Winchester self-catering cottage is situated a 5-minute drive (8 km) from Winchester's Old Town walking mall and 30 minutes (48 km) from the Blue Ridge Mountains, offering easy access to Shenandoah Valley attractions.
The 1-bedroom, 1-bathroom property sleeps 2 guests and features a queen-size bed in a loft, laundry facilities, a private patio overlooking a zen garden, a fire pit, and access to organic vegetable/herb gardens.

Best Winchester, VA accommodations with a kitchen

Winchester Farm - Winchester, VA
10 13 reviews

Winchester Farm

apartment, Winchester
House/cottage 2bed, Private Yard, Walk To Oldtown - Winchester, VA
9.8 48 reviews

House/cottage 2bed, Private Yard, Walk To Oldtown

house, Winchester
Peaceful Secret Gardens Tiny Home - A Space To Relax And Get Away From It All. - Winchester, VA
10 11 reviews

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

B&B, Winchester
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

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.

Scarborough Fair Walk To Downtown Two Story Apt - Winchester, VA
9.8 7 reviews

Scarborough Fair Walk To Downtown Two Story Apt

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
9.8 138 reviews

Newly Repurposed Historic Home In Winchester Va!

apartment, Winchester
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