Winchester, WA Short term rentals

58 available short term rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Winchester, WA short term rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Short term and Weekly rentals in Winchester, WA

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.

We Welcome You To Winchester! Best Reviews! - Winchester, WA
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.
Cameron Charmer Pristine Downtown Apt With Double Master Suites - Winchester, WA
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.
Cameron Charmer Pristine W/double Master Suites - Winchester, WA
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.
Magnolia Wind 
3 Br 1 Ba Loft…
Walk To Downtown. - Winchester, WA
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

Private Studio Space - Winchester, WA
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.
Merrimans Hope 
5br Spacious & Stunning On 2 +Acre - Winchester, WA
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.
Scarborough Fair Walk To Downtown Two Story Apt - Winchester, WA
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.
Nostalgia Lane In The Heart Of The City - Winchester, WA
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

Destinations nearby

Best Winchester, WA lodging with laundry available

Downtown Fun! Personal Mid Century 2bd Apartment! - Winchester, WA
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.
Nostalgia Lane 3 Br In The Heart Of The City - Winchester, WA
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.
Historic District Charm On Cameron Street - 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.
The Queen Of Winchester - Three Bedroom Apartment - Winchester, WA
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

The Stock Exchange Downtown Hip Studio Apt - Winchester, WA
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.
Downtown Winchester Retreat! Steps To Old Town - Winchester, WA
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.
Morocco Loft 2br Overlooking The City - Winchester, WA
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.
Cozy Private Space Winchester,va - Winchester, WA
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.
©2026 cozycozy.com