Winchester, WA vacation rentalscozycozy

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Best Vacation rentals and Airbnb offers in Winchester, WA

City Charmer Minutes From Old Town - Winchester, WA
9.9 351 reviews
Winchester, WA
4 2
$201/nighttotal: $402 (2 )

City Charmer Minutes From Old Town

apartment - Winchester
This 2-bedroom house in Winchester is conveniently located within a 15-minute walk of Nalls Farm Market, Jim Barnett Park, and Mt Hebron Cemetery, making it easy to explore the city’s attractions. The home has consistently received excellent ratings for user experience, location, and cleanliness.
The 800 square foot house comfortably accommodates up to 4 guests and features a fully equipped kitchen, a relaxing garden, and a terrace. You can enjoy free Wi-Fi, air conditioning, and a DVD player for entertainment, as well as a smoke-free environment for a pleasant stay.
Scarborough Fair Walk To Downtown Two Story Apt - Winchester, WA
9.8 7 reviews
Winchester, WA
2 3
$397/nightfor 1 night

Scarborough Fair Walk To Downtown Two Story Apt

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.
Dreamweaver  1br 1ba Just Two Blocks From The Downtown Walking Mall - Winchester, WA
8.8 5 reviews
Winchester, WA
2 1
$230/nightfor 1 night

Dreamweaver 1br 1ba Just Two Blocks From The Downtown Walking Mall

apartment - Winchester
This Winchester apartment rental is conveniently located in the Historic District, within a 10-minute walk of Stonewall Jackson's Headquarters, the Handley Regional Library, and the Old Court House Civil War Museum.
The one-bedroom, one-bathroom unit sleeps two guests and features a fully equipped kitchen, free WiFi, a Smart TV, on-site parking, and a spa; housekeeping is available upon request.
Secret Gardens Carriage House - Winchester, WA
9.7 95 reviews
Winchester, WA
2 1
$85/nighttotal: $2550 (30 )

Secret Gardens Carriage House

apartment - Winchester
This charming carriage house is located in Winchester, Virginia, just a short drive from Old Town Winchester and the Blue Ridge Mountains. The property is situated on two acres of peaceful Zen gardens, offering a tranquil escape from the city. Guests consistently rate this rental excellent for location, cleanliness, and overall experience.
This unique apartment can accommodate two guests and features a private screened porch, a fire pit, and a private garden. Guests can enjoy organic amenities, explore the wildlife habitat, and relax in the serene gardens.
Easy Like A Sunday Morning 1 Br Apt Great Location - Winchester, WA
9.9 126 reviews
Winchester, WA
2 1
$150/nightfor 1 night

Easy Like A Sunday Morning 1 Br Apt Great Location

apartment - Winchester
This Winchester apartment is located on Fairmont Ave in the historic district, just two blocks from the Old Town Winchester pedestrian mall and one block from the Handley Library. The apartment enjoys excellent ratings for location, cleanliness, and overall user experience.
The apartment is a one-bedroom, one-bathroom unit that can accommodate two guests. It includes a fully equipped kitchen, a dedicated workspace, and comfortable amenities like a queen-sized bed, a sofa, and a shower/tub combo.
Winchester Farm - Winchester, WA
10 13 reviews
Winchester, WA
4 3
$680/nighttotal: $1360 (2 )

Winchester Farm

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.
Treasure House - Winchester, WA
9.7 12 reviews
Winchester, WA
2 3
$537/nightfor 1 night

Treasure House

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.
Cameron Street Retreat: King Bed & Office Downtown - Winchester, WA
9.8 26 reviews
Winchester, WA
2 1
$309/nightfor 1 night

Cameron Street Retreat: King Bed & Office Downtown

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.
New Charming 3-bedroom  2 Full Bath And 1 Half Bedrooms Single Family  House - Winchester, WA
8.6 10 reviews
Winchester, WA
2 3
$192/nighttotal: $5760 (30 )

New Charming 3-bedroom 2 Full Bath And 1 Half Bedrooms Single Family House

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.
3 Bedroom Upper Unit, Quiet Area Close To Town - Winchester, WA
9.8 12 reviews
Winchester, WA
4 3
$233/nighttotal: $466 (2 )

3 Bedroom Upper Unit, Quiet Area Close To Town

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.
Cameron Charmer Pristine W/double Master Suites - Winchester, WA
10 223 reviews
Winchester, WA
2 2
$302/nightfor 1 night

Cameron Charmer Pristine W/double Master Suites

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.
Scarborough Fair Walk To Downtown Two Story Apt - Winchester, WA
9.8 145 reviews
Winchester, WA
2 3
$351/nightfor 1 night

Scarborough Fair Walk To Downtown Two Story Apt

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.

Discover Central Vacation Rentals in Winchester, WA

Stay in downtown Winchester, WA to keep top attractions within walking distance. Browse our central vacation rentals and find your perfect base.

Brewhouse Renovated Row House Steps From Downtown - Winchester, WA
9.9 106 reviews
Winchester, WA
2 2
$112/nighttotal: $3360 (30 )

Brewhouse Renovated Row House Steps From Downtown

house - Winchester
This charming house is located in downtown Winchester, just a short walk from the Old Town Winchester walking mall and a quick drive from the Handley Library and the Museum of the Shenandoah Valley. The house consistently receives excellent ratings for location, cleanliness, and user experience, making it a popular choice for travelers.
The home features two bedrooms with comfortable beds and two full bathrooms, accommodating up to four guests. Enjoy amenities like a fully equipped kitchen, air conditioning, a fenced backyard, and free parking, ensuring a comfortable and enjoyable stay.
Nostalgia Lane In The Heart Of The City - Winchester, WA
9.2 17 reviews
Winchester, WA
2 3
$330/nightfor 1 night

Nostalgia Lane In The Heart Of The City

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.
Wonderclock House Steps From Handley Library - Winchester, WA
9.5 183 reviews
Winchester, WA
2 3
$351/nightfor 1 night

Wonderclock House Steps From Handley Library

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.
Old Town Modern Twist! Rock N Roll Fun W/parking! - Winchester, WA
9.9 207 reviews
Winchester, WA
2 2
$264/nightfor 1 night

Old Town Modern Twist! Rock N Roll Fun W/parking!

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.

Best Winchester, WA vacation rentals with air conditioning

The Stock Exchange Downtown Hip Studio Apt - Winchester, WA
9.7 78 reviews
Winchester, WA
2 1
$71/nighttotal: $2130 (30 )

The Stock Exchange Downtown Hip Studio Apt

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.
The Cozy Brick Cottage On Opequon Ave - Winchester, WA
Winchester, WA
2 3
$105/nighttotal: $3150 (30 )

The Cozy Brick Cottage On Opequon Ave

apartment - Winchester
This 3-bedroom, 1-bathroom cottage offers a prime location in Winchester, just 5 minutes from historic Old Town and a 20-minute drive from Shenandoah National Park and local wineries.
This pet-friendly rental accommodates up to 6 guests, featuring air conditioning, internet, a full kitchen, and a private porch with a sunny yard, all with dedicated driveway parking.
Dreamweaver
Bright 1br  
2 Blocks To Walking Mall - Winchester, WA
9.7 49 reviews
Winchester, WA
2 1
$204/nightfor 1 night

Dreamweaver Bright 1br 2 Blocks To Walking Mall

apartment - Winchester
This Winchester apartment rental is conveniently located in the downtown area, two blocks from the pedestrian mall and walking distance to the Handley Library, offering easy access to historical sites, museums, and hiking trails like Bears Den.
The second-floor unit features one bedroom, one bathroom, sleeps three guests comfortably with a queen bed and futon, and includes a fully equipped kitchen, free on-site parking, and coin-operated laundry.
Wonderclock House Downtown Vintage Duplex W/ Porches, Steps To Handley Library - Winchester, WA
9.0 10 reviews
Winchester, WA
2 3
$367/nightfor 1 night

Wonderclock House Downtown Vintage Duplex W/ Porches, Steps To Handley Library

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.

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.

Popular destinations

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.

191 M² House ∙ 3 Bedrooms ∙ 6 Guests - Winchester, WA
Winchester, WA
2 3
$138/nighttotal: $4140 (30 )

191 M² House ∙ 3 Bedrooms ∙ 6 Guests

house - Winchester
Vacation rental for 6 people. You will stay in Winchester.
Facilities and services include a garden, a kitchen and an iron. Take advantage of the Free Parking with this accommodation in Winchester!

Neighborhoods and points of interest 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.

Magnolia Wind 
3 Br 1 Ba Loft
Walk To Downtown. - Winchester, WA
9.6 26 reviews
Winchester, WA
2 3
$349/nightfor 1 night

Magnolia Wind 3 Br 1 Ba Loft Walk To Downtown.

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.
Cameron Charmer Pristine Downtown Apt With Double Master Suites - Winchester, WA
9.6 9 reviews
Winchester, WA
2 2
$346/nightfor 1 night

Cameron Charmer Pristine Downtown Apt With Double Master Suites

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.
Cleveland Park Bright 2br Apt Blocks From Downtown - Winchester, WA
9.5 110 reviews
Winchester, WA
2 2
$279/nightfor 1 night

Cleveland Park Bright 2br Apt Blocks From Downtown

apartment - Winchester
This ground-floor apartment in Cleveland Park is located just two blocks from Winchester's pedestrian mall, placing you within easy walking distance of shops, restaurants, and entertainment. Guests consistently rate the apartment excellent for its location, cleanliness, and overall experience.
The two-bedroom apartment comfortably accommodates five guests with a full-sized sofa futon in the living room. Amenities include air conditioning, parking, a fully equipped kitchen, and internet access, making your stay convenient and enjoyable.

Best Winchester, WA vacation rentals with parking

Queen Of Winchester - Three Bedroom Apartment - Winchester, WA
9.6 64 reviews
Winchester, WA
4 3
$278/nighttotal: $556 (2 )

Queen Of Winchester - Three Bedroom Apartment

apartment - Winchester
Modern Elegance In Historic Old Town Winchester - Winchester, WA
9.9 313 reviews
Winchester, WA
2 1
$201/nightfor 1 night

Modern Elegance In Historic Old Town Winchester

house - Winchester
Yellow Submarine Trendy Basement Apt W/courtyard - Winchester, WA
9.5 131 reviews
Winchester, WA
4 3
$250/nighttotal: $500 (2 )

Yellow Submarine Trendy Basement Apt W/courtyard

apartment - Winchester
Downtown Fun! Personal Mid Century 2bd Apartment! - Winchester, WA
9.8 277 reviews
Winchester, WA
2 2
$273/nightfor 1 night

Downtown Fun! Personal Mid Century 2bd Apartment!

apartment - Winchester

Find the Best Luxury Vacation Rentals in Winchester, WA

Discover ultimate relaxation in a luxury Winchester, WA vacation rental, where comfort meets a central, prime location.

Old Town Modern Twist! Rock N Roll Fun W/parking! - Winchester, WA
9.9 207 reviews
Winchester, WA
2 2
$264/nightfor 1 night

Old Town Modern Twist! Rock N Roll Fun W/parking!

apartment - Winchester

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.

Dragonfly Inn Ii  Fabulous 2br 1ba Modern Downtown Apt  Walk To Everything - Winchester, WA
Winchester, WA
2 2
$346/nightfor 1 night

Dragonfly Inn Ii Fabulous 2br 1ba Modern Downtown Apt Walk To Everything

apartment - Winchester
Newly Repurposed Historic Home In Winchester Va! - Winchester, WA
9.8 143 reviews
Winchester, WA
2 1
$168/nightfor 1 night

Newly Repurposed Historic Home In Winchester Va!

apartment - Winchester
The Blue Door Steps From Handley Library - Winchester, WA
9.5 116 reviews
Winchester, WA
2 1
$178/nightfor 1 night

The Blue Door Steps From Handley Library

apartment - Winchester

Top-Rated Vacation Rentals with a Pool in Winchester, WA

A vacation rental with a pool in Winchester, WA makes it easy to fit in a proper swim right in the heart of the city.

Winchester Farm - Winchester, WA
10 13 reviews
Winchester, WA
4 3
$680/nighttotal: $1360 (2 )

Winchester Farm

apartment - Winchester

Top Vacation Rentals with a Hot Tub in Winchester, WA

Unwind after a day of urban exploration with a private hot tub at your own vacation rental in Winchester, WA.

New Charming 3-bedroom  2 Full Bath And 1 Half Bedrooms Single Family  House - Winchester, WA
8.6 10 reviews
Winchester, WA
2 3
$192/nighttotal: $5760 (30 )

New Charming 3-bedroom 2 Full Bath And 1 Half Bedrooms Single Family House

apartment - Winchester
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