Best Short term and Weekly rentals in Winchester, WA
Winchester, WA
06/28 – 07/05
$158/nighttotal: $1106 (7 )
George Washington L King Bed L Vanity For Two
1 2
B&B , Winchester
This historic inn in Winchester is located minutes from Skyline Drive, a renowned scenic byway, offering a blend of elegance and modern comfort. The 322 sq. ft. rooms, accommodating up to two guests, feature a king bed, dual vanities, premium cable TV, complimentary daily cleaning, 24/7 fitness center access, and a year-round indoor heated shared pool, with cooked-to-order breakfast available for an additional fee.
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.
9.9 62 reviews
Winchester, WA
06/28 – 07/05
$98/nighttotal: $686 (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.
10 1 review
Winchester, WA
09/02 – 09/06
$200/nighttotal: $800 (4 )
3 Bedroom Upper Unit, Quiet Area Close To Town
1 4
apartment , Winchester
This 3-bedroom, 1-bathroom apartment is located just under 3 miles from downtown Winchester and a 5-minute drive from Shenandoah University, offering a serene setting on a double lot backing up to a park in a quiet cul-de-sac. This rental accommodates up to 8 guests and features a well-equipped kitchen with a dishwasher and coffee essentials, along with a wrap-around porch for outdoor relaxation.
10 4 reviews
Winchester, WA
06/28 – 07/05
$191/nighttotal: $1337 (7 )
Cozy & Charming Downtown Apartment
1 2
apartment , Winchester
This first-floor apartment is located in historic downtown Winchester, Virginia, within walking distance to Handley Library and offering convenient access to attractions such as Bear's Den (approximately 10 miles away), Skyline Drive, and the Museum of the Shenandoah Valley. This 1-bedroom, 1-bathroom condo accommodates up to 2 guests and features air conditioning, internet, a full kitchen with a fridge, freezer, and microwave, plus free assigned on-site parking.
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.
9.5 116 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 5 reviews
Winchester, WA
09/02 – 09/06
$265/nighttotal: $1060 (4 )
Magnolia Wind Elegant 3 Br 1ba Loft Apartment Park For Free And Walk Downtown
3 4
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.
9.8 131 reviews
Winchester, WA
10/31 – 11/01
$251/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.
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.
9.3 61 reviews
Winchester, WA
10/31 – 11/01
$252/nightfor 1 night
Cozy English Basement Apt
1 2
B&B , Winchester
This cozy English basement apartment is located in downtown Winchester, just four blocks from the walking mall and other attractions. It has received excellent ratings for its location, cleanliness, and overall experience. The studio has a separate entrance and can accommodate up to two guests. It features a kitchenette with a microwave and toaster oven, a private bathroom, and a washer and dryer for added convenience.
9.4 32 reviews
Winchester, WA
06/28 – 07/05
$227/nighttotal: $1589 (7 )
Award Winning Hotel
1 2
B&B , Winchester
This Winchester bed and breakfast is located at the top of the Shenandoah Valley, just one mile from downtown Winchester and a quarter mile from Interstate 81. It boasts excellent user, location, and cleanliness ratings, making it a great choice for travelers. The inn features one bedroom and one bathroom, accommodating up to four guests. Amenities include air conditioning, internet, a swimming pool, parking, and pet-friendly accommodations.
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.
9.9 230 reviews
Winchester, WA
06/28 – 07/05
$78/nighttotal: $546 (7 )
We Welcome You To Winchester! Best Reviews!
1 2
apartment , Winchester
This charming bed and breakfast is located just a mile from Winchester's Old Town, offering easy access to the city's attractions while being situated on a quiet street. Guests consistently rate it excellent for its location, cleanliness, and overall experience. The inn features a comfortable guest room with a memory foam bed, a private A/C unit, and a shared bathroom, accommodating up to three guests. Enjoy a relaxing view of the garden, a welcome plate of snacks and drinks, and the option to join local tours and activities hosted by the friendly owners.
9.6 7 reviews
Winchester, WA
06/28 – 07/05
$205/nighttotal: $1435 (7 )
Cameron Charmer Pristine Downtown Apt With Double Master Suites
2 2
apartment , Winchester
This Winchester vacation home is 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 key historical sites. This two-bedroom, three-bathroom rental sleeps four guests and features a fully equipped kitchen with microwave and dishwasher, in-unit laundry, a Smart TV, air conditioning, and convenient on-site parking.
10 217 reviews
Winchester, WA
06/28 – 07/05
$140/nighttotal: $980 (7 )
Cameron Charmer Pristine W/double Master Suites
1 2
apartment , Winchester
This renovated 1930s home in downtown Winchester, Virginia, is a five-minute walk from the Old Town walking mall, near Shenandoah University and the Handley Library. This two-bedroom, two-bathroom house offers 1,600 square feet of living space, including a dine-in kitchen, a private garden, and parking for one car, accommodating up to four guests.
9.6 25 reviews
Winchester, WA
09/02 – 09/06
$264/nighttotal: $1056 (4 )
Magnolia Wind
3 Br 1 Ba Loft…
Walk To Downtown.
3 4
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.
Best Winchester, WA lodging with a kitchen
9.8 10 reviews
Winchester, WA
06/28 – 07/05
$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.
Winchester, WA
06/28 – 07/05
$476/nighttotal: $3332 (7 )
Merrimans Hope
5br Spacious & Stunning On 2 +Acre
1 2
apartment , Winchester
This five-bedroom, two-bathroom estate offers a secluded country ambiance on nearly 3 acres in Winchester, Virginia, just a 5-minute drive from downtown Winchester. This spacious residence accommodates up to 10 guests and features a gourmet kitchen, formal living room with a piano, a master suite with an en-suite bath on the first floor, and outdoor spaces including porches, decks, and patios, along with a hot tub.
9.8 136 reviews
Winchester, WA
06/28 – 07/05
$225/nighttotal: $1575 (7 )
Scarborough Fair Walk To Downtown Two Story Apt
1 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.
9.0 16 reviews
Winchester, WA
06/28 – 07/05
$192/nighttotal: $1344 (7 )
Nostalgia Lane In The Heart Of The City
3 2
apartment , Winchester
This Old Town Winchester apartment is steps from the Bright Box Theater and Old Court House Civil War Museum, with the Shenandoah Valley Discovery Museum and George Washington's Office within a 5-minute walk. This 1100-square-foot rental boasts three bedrooms, one bathroom, and sleeps six, featuring in-unit amenities such as a dryer, TV, and hair dryer.
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
9.8 263 reviews
Winchester, WA
09/02 – 09/06
$167/nighttotal: $668 (4 )
Downtown Fun! Personal Mid Century 2bd Apartment!
1 4
apartment , Winchester
This Winchester apartment is located in the historic district, just a block from the Old Town Walking Mall, making it easy to explore shops, restaurants, and museums. The apartment has received excellent ratings for location, cleanliness, and user experience. The apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. Enjoy modern amenities such as a fully-equipped kitchen, air conditioning, high-speed internet, and a shared laundry room.
9.7 235 reviews
Winchester, WA
06/28 – 07/05
$138/nighttotal: $966 (7 )
Nostalgia Lane 3 Br In The Heart Of The City
1 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.
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.
9.7 53 reviews
Winchester, WA
06/28 – 07/05
$159/nighttotal: $1113 (7 )
The Queen Of Winchester - Three Bedroom Apartment
1 2
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.
Neighborhoods and points of interest in Winchester, WA
Best Winchester, WA lodging with air conditioning
9.7 76 reviews
Winchester, WA
06/28 – 07/05
$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.
Winchester, WA
06/28 – 07/05
$440/nighttotal: $3080 (7 )
Downtown Winchester Retreat! Steps To Old Town
1 2
apartment , Winchester
This 4-bedroom, 1-bathroom rental unit is located on Piccadilly in Winchester, a short walk from the Historic Downtown Walking Mall, numerous dining establishments, breweries, and the George Washington Hotel. This apartment accommodates up to 6 guests and offers internet, air conditioning, a kitchen, and on-street parking, with a front porch for outdoor relaxation.
9.5 56 reviews
Winchester, WA
09/02 – 09/06
$209/nighttotal: $836 (4 )
Morocco Loft 2br Overlooking The City
1 4
apartment , Winchester
This Winchester loft apartment is located on the third floor of a Tudor-style building overlooking Boscawen Street, just steps away from the walking mall, the Discovery Museum, and numerous shops and restaurants. The apartment has received excellent ratings for its location, cleanliness, and overall experience. The loft features two bedrooms, a small office, a dining area, a kitchen, and a bathroom with a tub and laundry facilities. Guests can enjoy amenities like air conditioning, parking, and internet, along with panoramic views of the city from the third floor.
9.9 45 reviews
Winchester, WA
10/31 – 11/01
$134/nightfor 1 night
Cozy Private Space Winchester,va
1 2
apartment , Winchester
This Winchester, Virginia guesthouse offers a private, self-contained unit near Fox Meadow Barn, Winchester Medical Center, and Old Town Winchester. The one-bedroom, one-bathroom suite sleeps three guests and includes a queen bed, queen sofa bed, microwave, mini-fridge, coffee station, private parking, and a covered porch; self check-in is available.