Best Short term and Weekly rentals in Winchester, WA
9.8 171 reviews
Winchester, WA
09/02 – 09/06
$180/nighttotal: $720 (4 )
Historic District Charm On Cameron Street
1 4
apartment , Winchester
This historic district apartment in Winchester, Virginia is a short walk from the Winchester Walking Mall, Shenandoah University, and the Museum of the Shenandoah Valley. The three-bedroom rental features a full kitchen, dining room, family room, dedicated workspace, large private deck, half-court basketball court, and accommodates up to four guests (six for a minimal fee), with one bathroom.
10 10 reviews
Winchester, WA
09/02 – 09/06
$620/nighttotal: $2480 (4 )
Winchester Farm
1 4
apartment , Winchester
This Winchester farm stay, perfect for families, boasts three bedrooms and two bathrooms, comfortably accommodating six guests and offering amenities such as a swimming pool, fitness center, and internet access. The property includes a fully equipped kitchen, parking, and allows pets; further details on its precise Winchester location and proximity to local attractions are unavailable.
9.7 53 reviews
Winchester, WA
09/02 – 09/06
$180/nighttotal: $720 (4 )
The Queen Of Winchester - Three Bedroom Apartment
1 4
apartment , Winchester
This three-bedroom Winchester apartment boasts an excellent location, offering easy access to the city's attractions—though precise distances require further information. The upper-level rental features a private terrace, accommodates four guests, and includes amenities such as air conditioning, internet, parking, and pet-friendliness.
Winchester, WA
10/31 – 11/01
$309/nightfor 1 night
Dragonfly Inn Ii \Nfabulous 2br 1ba Modern Downtown Apt Walk To Everything
2 2
apartment , Winchester
This 2-bedroom rental is located in downtown Winchester's city center, one block from the walking mall and close to the Shenandoah Valley Discovery Museum. This 680 sq ft residence accommodates up to 3 guests and features a fully equipped kitchen, in-unit laundry, air conditioning, spa access, and free parking, with opportunities for kayaking, mountain climbing, and hiking nearby.
9.9 198 reviews
Winchester, WA
09/02 – 09/06
$165/nighttotal: $660 (4 )
Old Town Modern Twist! Rock N’ Roll Fun W/parking!
1 4
apartment , Winchester
This Winchester apartment is located in the downtown area, within walking distance of the Shenandoah Valley Museum, Glen Bernie trails, and a variety of restaurants, bars, and shops. It has received excellent ratings for location, cleanliness, and user experience. The rental offers two bedrooms and one bathroom, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen, a dedicated workspace, high-speed internet, a free washer and dryer, private parking, and a comfortable living area with a 55-inch smart TV.
9.8 7 reviews
Winchester, WA
07/06 – 07/07
$405/nightfor 1 night
Scarborough Fair Walk To Downtown Two Story Apt
3 2
apartment , Winchester
This Old Town Winchester apartment rental is conveniently located within a 10-minute walk of the Handley Regional Library, the Old Court House Civil War Museum, and the Bright Box Theater, placing you near key historical sites. This 2,250-square-foot apartment sleeps up to 10 guests and boasts three bedrooms, one bathroom, in-unit laundry, a fireplace, a Smart TV, and a well-equipped kitchen with a refrigerator and microwave, plus free parking and air conditioning.
Winchester, WA
07/06 – 07/07
$187/nightfor 1 night
King + Sofa Bed L George Washington L Downtown
1 2
B&B , Winchester
This downtown Winchester inn is situated in the Shenandoah Valley, offering a stylish retreat near local attractions. This accommodation features one bedroom and one bathroom, accommodating up to two guests, with amenities including internet, air conditioning, a swimming pool, fitness center, and paid valet parking.
9.6 8 reviews
Winchester, WA
07/27 – 08/03
$113/nighttotal: $791 (7 )
Cozy English Basement Apt Quiet But Close To Downtown
1 2
apartment , Winchester
This Winchester apartment rental is conveniently located within a 10-minute walk of the Winchester Little Theatre, George Washington's Office, and the Shenandoah Valley Discovery Museum. This one-bedroom, one-bathroom unit sleeps two guests and includes in-unit laundry, free Wi-Fi, air conditioning, and essential amenities such as a TV, hairdryer, and iron/ironing board; nearby attractions include the Bright Box Theater and Old Court House Civil War Museum (within a 15-minute radius).
9.5 177 reviews
Winchester, WA
07/06 – 07/07
$371/nightfor 1 night
Wonderclock House Steps From Handley Library
1 2
apartment , Winchester
This three-bedroom Winchester apartment rental is ideally located downtown, steps from the Handley Library and the pedestrian mall, providing easy access to numerous restaurants and shops. The duplex features a fully equipped kitchen, one bathroom, a clawfoot tub, three porches, and accommodates up to six guests; nearby laundry access is available.
9.7 76 reviews
Winchester, WA
07/27 – 08/03
$102/nighttotal: $714 (7 )
The Stock Exchange Downtown Hip Studio Apt
1 2
apartment , Winchester
This downtown Winchester studio apartment is located a block and a half from the Winchester Walking Mall, providing easy access to shopping, dining, and other attractions. The third-floor unit features a full-sized futon, a flat-screen TV, on-site laundry, free parking, and can comfortably accommodate two guests with a fridge and microwave.
9.9 62 reviews
Winchester, WA
07/27 – 08/03
$97/nighttotal: $679 (7 )
Retro Vibe Studio
1 2
B&B , Winchester
This newly finished basement studio apartment is located in Winchester, Virginia, a short walk from the downtown area, the walking mall, and numerous restaurants, with easy access to Skyline Drive and Harpers Ferry. This 1-bathroom unit sleeps 2 guests and features a kitchen with a fridge and microwave, air conditioning, on-site parking, a private entrance, and a garden, offering a comfortable and convenient stay near Shenandoah University and Winchester Medical Center.
9.7 235 reviews
Winchester, WA
07/27 – 08/03
$138/nighttotal: $966 (7 )
Nostalgia Lane 3 Br In The Heart Of The City
3 2
apartment , Winchester
This Winchester apartment is located on Boscawen Street in the heart of downtown, just steps from the Winchester Walking Mall and within easy walking distance of the John Handley Library, Discovery Museum, and various restaurants and shops. The three-bedroom apartment features a spacious living room with a flat-screen TV, a fully equipped kitchen with a refrigerator and microwave, a laundry area, and a full bathroom, comfortably accommodating up to six guests.
Discover Family Short-Term Rentals in Winchester, WA
Family trips to Winchester, WA are made simple with urban rentals that keep city attractions within easy walking distance.
9.2 7 reviews
Winchester, WA
07/06 – 07/07
$372/nightfor 1 night
Wonderclock House Downtown Vintage Duplex W/ Porches, Steps To Handley Library
3 2
apartment , Winchester
This Old Town Winchester apartment rental is conveniently located within a 10-minute walk of the Handley Regional Library, the Old Court House Civil War Museum, and Stonewall Jackson's Headquarters. This 1250-square-foot three-bedroom, two-bathroom unit sleeps six and includes Wi-Fi, air conditioning, an in-unit TV, and a hair dryer; nearby attractions include the Bright Box Theater and Winchester Little Theater.
10 4 reviews
Winchester, WA
07/27 – 08/03
$155/nighttotal: $1085 (7 )
Cameron Grace Brand New 1br 1ba Apt Downtown Winchester
1 2
apartment , Winchester
This Winchester apartment rental is conveniently located within a 10-minute walk of the Patsy Cline Historic House, Shenandoah Valley Discovery Museum, and George Washington's Office, offering easy access to Winchester's historic district. This one-bedroom, one-bathroom unit sleeps two guests and features a fully equipped kitchen with a refrigerator, microwave, dishwasher, and in-unit laundry; on-site parking is also provided.
8.8 9 reviews
Winchester, WA
07/27 – 08/03
$274/nighttotal: $1918 (7 )
New Charming 3-bedroom 2 Full Bath And 1 Half Bedrooms Single Family House
3 2
apartment , Winchester
This Winchester townhome offers easy access to Shenandoah Valley Discovery Museum, Nalls Farm Market, Summit Point Motorsports Park, and Barns of Rose Hill, though precise distances aren't specified. This three-bedroom, four-bathroom house sleeps 30 guests, features a king, queen, and full bed, an office with a futon, in-unit laundry, and complimentary WiFi, plus air conditioning and parking.
9.8 136 reviews
Winchester, WA
07/06 – 07/07
$356/nightfor 1 night
Scarborough Fair Walk To Downtown Two Story Apt
3 2
apartment , Winchester
This apartment is located in downtown Winchester, within walking distance of the Handley Library, the walking mall, and various shops and restaurants. It has excellent user, location, and cleanliness ratings. This rental offers three bedrooms and one bathroom, comfortably accommodating up to eight guests. The apartment features a fully equipped kitchen, a fenced yard, and three porches, making it perfect for families, groups, or pet owners.
Best Winchester, WA lodging with a kitchen
9.5 116 reviews
Winchester, WA
10/31 – 11/01
$279/nightfor 1 night
The Blue Door Steps From Handley Library
1 2
apartment , Winchester
This downtown Winchester studio apartment is conveniently located near the Handley Library and two blocks from the Winchester walking mall, offering easy access to Shenandoah University and Winchester Medical Center (5-minute drive). This pet-friendly unit sleeps two, features a full kitchen with a fridge and microwave, a 32” flat-screen TV with Roku, on-site laundry, and two complimentary parking spaces; nearby attractions include the Skyline Drive (30-minute drive) and Washington, D.C. (1.5-hour drive).
10 11 reviews
Winchester, WA
07/27 – 08/03
$117/nighttotal: $819 (7 )
Peaceful Secret Gardens Tiny Home - Loft & Stairs Lead To A Queen Size Bed
1 2
B&B , Winchester
This Winchester guesthouse is conveniently located within 3 miles of the Kernstown Battlefield, Shenandoah University, and Apple Blossom Mall, offering easy access to historical sites, higher education, and shopping. This smoke-free, one-bedroom, one-bathroom bed and breakfast accommodates two guests and features a fitness center, terrace, garden, on-site laundry, and parking; housekeeping is available upon request.
9.8 10 reviews
Winchester, WA
07/27 – 08/03
$89/nighttotal: $623 (7 )
Private Studio Space
1 2
B&B , Winchester
This studio apartment is conveniently located in Winchester, within easy walking distance of the city's historic landmarks like Winchester Cathedral and the Great Hall. It's received excellent ratings for location, cleanliness, and overall experience. The apartment is a cozy space perfect for a couple or solo traveler. It comes equipped with a kitchen, air conditioning, and a private garden, making it easy to relax and enjoy your stay in Winchester.
9.8 19 reviews
Winchester, WA
07/27 – 08/03
$117/nighttotal: $819 (7 )
Secret Gardens Carriage House
1 2
B&B , Winchester
This smoke-free Winchester guesthouse, located 1.2 miles from Kernstown Battlefield and within 3 miles of Apple Blossom Mall and Shenandoah University, offers a peaceful residential setting near numerous attractions. This 800-square-foot, one-bedroom, one-bathroom guesthouse comfortably accommodates two guests and includes amenities such as air conditioning, a fridge, a terrace, a garden, and parking.
Frequently Asked Questions about short term rentals in Winchester, WA
What notable natural landmarks are near Winchester, VA?
Winchester is surrounded by some beautiful natural landmarks. The Skagit River is a great place to go for a walk or bike ride, and the Mount Baker-Snoqualmie National Forest is a great place to hike, camp, and enjoy the scenery. If you're looking for a more unique experience, check out the Ross Lake National Recreation Area, which is home to a variety of hiking trails and stunning views.
What are the best short term rentals in Winchester, WA?
What part of Winchester, VA is ideal for finding lodging?
Winchester is a small town, so you won't find a lot of hotels. You'll find a few small motels and bed and breakfasts in town, but most travelers stay in nearby towns like Mount Vernon or Burlington. These towns have a wider variety of lodging options, including hotels, motels, and vacation rentals.
What are the best short term rentals with a pool in Winchester, WA?
The best short term rental with a pool in Winchester, WA is Quiet Country Living.
What are the best short term rentals with a jacuzzi in Winchester, WA?
Best Winchester, WA lodging with laundry available
9.8 135 reviews
Winchester, WA
07/06 – 07/07
$191/nightfor 1 night
Newly Repurposed Historic Home In Winchester Va!
1 2
apartment , Winchester
This charming apartment is located in Winchester, close to Old Town, Shenandoah University, and Winchester Medical Center, offering easy access to shops, restaurants, and attractions. It has received excellent ratings for location, cleanliness, and user experience. The apartment features a private patio, a shared garden, and a kitchenette with a refrigerator, microwave, and coffee maker. Enjoy modern amenities like high-speed internet, a 50-inch smart TV, and a washer and dryer, along with the convenience of being pet-friendly and suitable for extended stays.
10 5 reviews
Winchester, WA
07/27 – 08/03
$156/nighttotal: $1092 (7 )
Magnolia Wind Elegant 3 Br 1ba Loft Apartment Park For Free And Walk Downtown
3 2
apartment , Winchester
This Winchester Old Town apartment is conveniently located within walking distance of Handley Regional Library and Stonewall Jackson's Headquarters, offering easy access to historical sites. The three-bedroom, one-bathroom rental features a fully equipped kitchen with dishwasher and microwave, in-unit laundry, air conditioning, parking, and Wi-Fi, comfortably accommodating up to six guests and providing easy access to nearby shopping and outdoor recreation areas like Northside Station and Abrams Creek Wetlands Preserve.
9.8 46 reviews
Winchester, WA
07/27 – 08/03
$205/nighttotal: $1435 (7 )
House/cottage 2bed, Private Yard, Walk To Oldtown
1 2
apartment , Winchester
This charming cottage is located just a short walk from downtown Winchester, offering easy access to restaurants, shops, and entertainment. It has received excellent ratings for its cleanliness, location, and overall user experience. The cottage provides comfortable accommodations for two guests with a fully equipped kitchen and a private backyard with a fire pit. Guests can enjoy amenities like air conditioning, a fenced garden, and parking, along with a cozy front porch for relaxing.
8.0 7 reviews
Winchester, WA
10/31 – 11/01
$401/nightfor 1 night
2 Bedroom Condo In Stephens City
1 2
apartment , Stephens City
This Stephens City, Virginia condo is located approximately 10 minutes from historic downtown Winchester and an hour from Washington, D.C., and Luray Caverns. The two-bedroom, two-bathroom apartment offers guests internet, air conditioning, parking, and a kitchen, accommodating up to four people and is near a lake, nature trail, and local library.
Neighborhoods and points of interest in Winchester, WA
Best Winchester, WA lodging with air conditioning
9.8 404 reviews
Winchester, WA
07/27 – 08/03
$200/nighttotal: $1400 (7 )
Old Town 1920s Gas Station With Hot Tub
1 2
apartment , Winchester
This charming apartment sits in Old Town Winchester, just a five-minute walk from the downtown walking mall, breweries, and the Pizzoco Pizza parlor. The apartment enjoys excellent ratings for location, cleanliness, and user experience. The apartment has one bedroom and one bathroom, comfortably accommodating two guests. Enjoy modern amenities like a full kitchen, a smart TV, high-speed Wi-Fi, and a washer/dryer, as well as unique features like voice-controlled smart home features, off-street parking, and an EV charging station.
Winchester, WA
07/06 – 07/07
$148/nightfor 1 night
King Room L George Washington L Double Vanity
1 2
B&B , Winchester
This historic hotel in Winchester offers elegant accommodations minutes from Skyline Drive, a renowned scenic route. The B&B features 322 sq. ft. rooms with a king bed and dual vanities, accommodating up to two guests, and includes amenities such as air conditioning, internet, a year-round indoor heated shared pool, and a 24/7 shared fitness center, with paid valet parking available.
9.3 76 reviews
Winchester, WA
09/02 – 09/06
$142/nighttotal: $568 (4 )
Modern Hotel With Small Town Charm
1 4
B&B , Winchester
This Winchester, Virginia bed and breakfast boasts a prime location atop the Shenandoah Valley, offering stunning views and proximity to Shenandoah University, Skyline Drive, and the Appalachian Trail. The one-bedroom, one-bathroom guesthouse comfortably sleeps four guests and features amenities including air conditioning, internet access, parking, and a swimming pool; pets are welcome.
9.6 25 reviews
Winchester, WA
07/27 – 08/03
$146/nighttotal: $1022 (7 )
Magnolia Wind
3 Br 1 Ba Loft…
Walk To Downtown.
3 2
apartment , Winchester
This downtown Winchester apartment is located directly across from the John Handley Library and two blocks from the Old Town Walking Mall, offering easy access to shops and restaurants. The fully renovated 1920s loft features a king-size bed, queen bed, two twin beds, and a pull-out sofa bed, accommodating up to seven guests, and includes a fully stocked kitchen, free private parking, and a sun porch.