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Winchester, WA vacation rentals
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Best Vacation rentals and Airbnb offers in Winchester, WA

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.

New Charming 3-bedroom  2 Full Bath And 1 Half Bedrooms Single Family  House - Winchester, WA
8.8 9 reviews
Winchester, WA
06/27 – 07/04
$273/nighttotal: $1911 (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.
Cameron Charmer Pristine Downtown Apt With Double Master Suites - Winchester, WA
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.
Scarborough Fair Walk To Downtown Two Story Apt - Winchester, WA
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.
Treasure House - Winchester, WA
10 3 reviews
Winchester, WA
06/27 – 07/04
$201/nighttotal: $1407 (7 )

Treasure House

1 2
apartment , Winchester
This Winchester house rental is conveniently located a 5-minute drive from Downtown Winchester, offering easy access to restaurants and a shopping mall.
The three-bedroom, two-bathroom home sleeps seven guests comfortably and includes a fully equipped kitchen, high-speed internet, ample parking, a dedicated office space, and a pet-friendly environment.

Best Winchester, WA vacation rentals with parking

Magnolia Wind Elegant 3 Br 1ba Loft Apartment Park For Free And Walk Downtown - Winchester, WA
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.
Cameron Grace Brand New 1br 1ba Apt Downtown Winchester - Winchester, WA
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.
Cameron Street Retreat: King Bed & Office Downtown - Winchester, WA
9.8 26 reviews
Winchester, WA
07/27 – 08/03
$140/nighttotal: $980 (7 )

Cameron Street Retreat: King Bed & Office Downtown

1 2
apartment , Winchester
This newly renovated Winchester apartment is located in the historic district, a 90-minute drive from Washington, D.C., and 40 minutes from Skyline Drive and Harpers Ferry.
The one-bedroom unit, sleeping up to two guests, features a king-size bed, queen-size pull-out sofa bed, in-unit laundry, dedicated office space, and complimentary off-street parking; starter supplies are provided.
Newly Repurposed Historic Home In Winchester Va! - Winchester, WA
9.8 135 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.

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?

    Immerse Yourself In Old Town Winchester (Apt #4), City Charmer Near Historic Oldtown Winchester and Downtown 1920's Gas Station With Hot Tub are the most popular Airbnb and vacation rentals in Winchester, WA among travelers.

  • 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?

    The best vacation rental with a pool in Winchester, WA is Quiet Country Living.

  • 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?

    The best vacation rentals or Airbnb with a jacuzzi in Winchester, WA are Downtown 1920's Gas Station With Hot Tub, Charming Family Luxury Home and Cozy Beautiful House.

  • 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.

Secret Gardens Tiny House - Winchester, WA
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.

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.

2 Bedroom Condo In Stephens City - Winchester, WA
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.
Wonderclock House Downtown Vintage Duplex W/ Porches, Steps To Handley Library - Winchester, WA
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.
Dragonfly Inn Ii \Nfabulous 2br 1ba Modern Downtown Apt  Walk To Everything - Winchester, WA
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.
Scarborough Fair Walk To Downtown Two Story Apt - Winchester, WA
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.
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