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Best Vacation rentals and Airbnb offers in Winchester, WA
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.
10 217 reviews
Winchester, WA
07/06 – 07/07
$354/nightfor 1 night
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.
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.
9.0 16 reviews
Winchester, WA
07/27 – 08/03
$190/nighttotal: $1330 (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.
9.5 58 reviews
Winchester, WA
07/27 – 08/03
$169/nighttotal: $1183 (7 )
Morocco Loft 2br Overlooking The City
2 2
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.
9.5 126 reviews
Winchester, WA
07/27 – 08/03
$137/nighttotal: $959 (7 )
Yellow Submarine Trendy Basement Apt W/courtyard
3 2
apartment , Winchester
This basement apartment is located in downtown Winchester, just steps away from the Handley Library and the walking mall, placing you in the heart of the city's cultural and entertainment scene. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience. The rental offers two bedrooms and one bathroom, comfortably accommodating up to four guests. The apartment features a fun Beatles theme, a vintage turntable and vinyl collection, a dedicated parking space, a shared laundry room, and the option to bring your furry friend along for an additional fee.
10 49 reviews
Winchester, WA
07/27 – 08/03
$113/nighttotal: $791 (7 )
Secret Gardens Tiny House
1 2
cabin , Winchester
This Winchester, Virginia tiny home, located in the Shenandoah Valley, is a five-minute drive from Old Town Winchester's walking mall and 30 minutes from the Blue Ridge Mountains. The one-bedroom, one-bathroom cottage sleeps two, features a queen-size bed in a loft, a kitchen with a fridge, air conditioning, a private patio overlooking zen gardens, access to a fire pit and shared organic gardens, and laundry facilities.
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 73 reviews
Winchester, WA
09/02 – 09/06
$110/nighttotal: $440 (4 )
Peaceful Family Retreat In The Heart Of Winchester
1 4
apartment , Winchester
This Winchester basement suite offers a private, keycode-accessible entrance in a quiet neighborhood, conveniently located a short drive from Winchester's shops and entertainment. The one-bedroom, one-bathroom apartment sleeps four guests comfortably, featuring a queen bed, bunk bed, board games, and a full bathroom; high-speed internet and air conditioning are also included.
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
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.
Compare Vacation Rentals for Families in Winchester, WA
These family-friendly vacation rentals in Winchester, WA offer spacious layouts and easy access to top city attractions.
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.
9.6 7 reviews
Winchester, WA
07/06 – 07/07
$346/nightfor 1 night
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 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.
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.
Best Winchester, WA vacation rentals with parking
10 1 review
Winchester, WA
09/02 – 09/06
$240/nighttotal: $960 (4 )
Cleveland Park Awesome Winchester 2 Br 1st Fl \Napt. Walk To Everything!
2 4
apartment , Winchester
This 2-bedroom, 1-bathroom apartment is located in the Winchester Historic District, a short walk from the downtown walking mall and its shops, restaurants, and cultural attractions like the Bright Box Theater and Old Court House Civil War Museum. This ground-floor rental accommodates up to 5 guests and features air conditioning, internet, a microwave oven, and parking, with proximity to Abrams Creek Wetlands Preserve and Shenandoah Valley Discovery Museum.
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.
9.8 7 reviews
Winchester, WA
10/31 – 11/01
$409/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.
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.
Frequently Asked Questions about vacation rentals in Winchester, WA
When is the best time to book a vacation rental in Winchester, VA?
The best time to book a vacation rental in Winchester is during the spring and summer months, especially around the Skagit Valley Tulip Festival in April. If you're looking for a quieter experience, you can book a rental during the fall or winter months.
What are the best Airbnb and vacation rentals in Winchester, WA?
What events or festivals should visitors check out in and around Winchester, VA?
The Skagit Valley Tulip Festival is the biggest event in the area, drawing thousands of visitors each year. The La Conner Quilt and Fiber Arts Festival is another popular event, held in September. If you're interested in music, the Skagit Valley Festival of Music is a great option, held every July.
What are the most popular Airbnbs in Winchester, WA?
What are the best budget-friendly activities in Winchester, VA?
Winchester is a small town with plenty of free or low-cost activities. You can enjoy a walk along the Skagit River, visit the Winchester Museum for a small fee, or explore the historic downtown area. There are also many hiking trails in the nearby Skagit Valley.
What are the best vacation rentals with a pool in Winchester, WA?
What are the best restaurants with local dishes in Winchester, VA?
Winchester has a few great restaurants serving local dishes. The Skagit River Grill is a popular choice for fresh seafood, while the Winchester Cafe serves up classic American comfort food. For a more casual experience, try the Winchester Pub, which is known for its burgers and local beers.
What are the best rentals for families and kids in Winchester, WA?
What are the best walking or cycling routes in Winchester, VA?
The Skagit River Trail is a great option for a leisurely walk or bike ride. The trail runs along the river for several miles, offering scenic views of the water and surrounding countryside. You can also find shorter walking trails in the downtown area and around the Winchester Museum.
What are the best rentals or Airbnbs with a jacuzzi in Winchester, WA?
Are there pet-friendly attractions in Winchester, VA?
Many of the parks and trails in Winchester are pet-friendly, including the Skagit River Trail and the downtown area. The Winchester Museum does not allow pets inside, but you can often find pet-friendly restaurants and cafes in the town.
Destinations nearby
Choose the Right Vacation Rentals with a Terrace in Winchester, WA
Start your morning right with a vacation rental in Winchester, WA featuring a private balcony and stunning views.
9.9 198 reviews
Winchester, WA
07/27 – 08/03
$129/nighttotal: $903 (7 )
Old Town Modern Twist! Rock N’ Roll Fun W/parking!
1 2
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.
Neighborhoods and points of interest in Winchester, WA
Discover Pet-Friendly Vacation Rentals in Winchester, WA
Experience a pet-friendly stay in Winchester, WA with vacation rentals located steps away from city dog parks and walking trails.
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.
9.6 8 reviews
Winchester, WA
07/06 – 07/07
$180/nightfor 1 night
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).
Winchester, WA
07/27 – 08/03
$440/nighttotal: $3080 (7 )
Downtown Winchester Retreat! Steps To Old Town
4 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.
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.