Apartment vacation rentals in Winchester

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Top-rated apartment rentals in Winchester

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Guest favorite

Apartment in Winchester

4.89 out of 5 average rating, 104 reviews

Modern Twist in Old Town! Rock n' Roll FUN!

Basil is your personal, 2 bedroom, Uber-stylish apartment, located in downtown Winchester with private parking! New & sparkling clean, enjoy high end finishes & creative design! Enjoy hot showers in the marble bath, sink into the shearling-covered couch relaxing in front of the new 55' smart TV, catch up with work in your private office, then walk to a great happy hour & dinner downtown! End your day cozying up in one of the two queen size, memory foam canopy beds! Basil is your perfect Airbnb!

Jun 12 – 19

G$21,450 GYD per night

Guest favorite

Apartment in Capon Bridge

4.99 out of 5 average rating, 114 reviews

Paw Paw Suite ~ 1 of 5 Unique Stays at Basswood

For those seeking to step away from the bustle of the city and slow down in a friendly, charming town. Basswood is a historic home that has been lovingly remodeled to include five private suites each with their own unique style. The Paw Paw Suite is an inviting space with a queen size bed, double shower bathroom, and kitchenette. Located in the heart of Capon Bridge, you'll find it easy to walk to everything. For a relaxing stay in a friendly, artsy community, this is a great place to enjoy.

Jan 2 – 9

G$17,146 GYD per night

Guest favorite

Apartment in Winchester

5.0 out of 5 average rating, 138 reviews

Old Town Loft In Highly Desirable Area Downtown

Location, Location! A completely renovated apartment in the highly desirable center Winchester. You’ll still be able to see some of its original character throughout this historic building. The apartment has a fully stocked custom kitchen with reclaimed wood and quartz counters, coffee nook with Keurig, large tile shower with glass doors, hardwood floors, queen memory foam mattress, high speed Wi-Fi, 50’ smart TV, Xfinity HDTV with voice remote control, AC/Heat, Washer/Dryer, and dishwasher.

Oct 7 – 14

G$34,460 GYD per night

Guest favorite

Apartment in Winchester

4.98 out of 5 average rating, 217 reviews

Downtowner

No hassle parking on premises and a private entrance. The "Downtowner" is a 1920's era restored home in a quiet residential section of Winchester's Historic District and just a short stroll to the downtown "pedestrian only" walking mall with restaurants, cafes, and shops. Clean and spacious, the apartment is complete with bed linens, towels, etc. and stocked with water in the fridge as well as a Keurig with coffee options, tea, hot chocolate, etc...Xfinity HDTV with voice remote control.

Jun 11 – 18

G$23,508 GYD per night

Guest favorite

Apartment in Winchester

4.94 out of 5 average rating, 272 reviews

Downtown 1920's Gas Station

Luxury 1920’s Refurbished Gas Station repurposed into a beautiful apartment. Private off-street parking/EV car charging station, full kitchen, custom shower with rain system, super high speed wifi, smart TV & Blu-Ray. Plenty of light with frosted garaged doors. AC/Heat, Washer/Dryer, Dish Washer, coffee nook, and open living design. Be a part of Old Town Winchester in this unique fun space in walking distance to breweries, neighborhood Pizzoco Pizza parlor and the downtown walking mall.

Nov 28 – Dec 5

G$35,417 GYD per night

Guest favorite

Apartment in Winchester

4.8 out of 5 average rating, 287 reviews

Pretty Little Apt by the Train II

This little place is just plain charming. Lots of light and personality. Wonderful alternative to the typical hotel experience. Fabulous for short term rental needs. Come enjoy Downtown Flat screen TV/ Record Player FREE PARKING/WIFI Near Piccadillys Pub, the Walking Mall, our beautiful and historic library, Shenandoah Univ. -5 minute Winchester Med Center -5 min DC. -1.5 hr Skyline Drive -30 min Free Parking too ! Reach out on social media if you need more. Michele Bouve Hoffman

Dec 6 – 13

G$21,122 GYD per night

Guest favorite

Apartment in Cumberland

4.99 out of 5 average rating, 324 reviews

Steeple View Flat in Historic District

Relax in your first level flat. Entire private efficiency suite with a secure self check in. The entrance located along side of the main house in Cumberland’s Historic District. You can safely park your car and walk to many of Cumberlands amenities. If you’re biking, they can be stored inside. Canal Place has unique shops a winery and a bike rental facility. Cumberland theater is adjacent to the property, also Baltimore St. Promenade offers a delicious choice of indoor and outdoor dining.

Apr 26 – May 3

G$20,478 GYD per night

Guest favorite

Apartment in Culpeper

4.98 out of 5 average rating, 147 reviews

TreeTop at Mt Run Lake (Private Guest Apartment)

Spacious one bedroom guest apartment with SEPARATE ENTRANCE, private separate patio and reserved parking in this newly decorated full apartment, set on four acres with lakefront views situated in the foothills of the Blue Ridge Mountains. One flight of stairs up to a beautiful apartment with fantastic views of the lake and surrounding property. Private and secluded yet only 10 minutes from Historic downtown Culpeper with its many restaurants, local shops, grocery stores and pharmacies.

Apr 11 – 18

G$23,118 GYD per night

Guest favorite

Apartment in The Plains

4.98 out of 5 average rating, 447 reviews

Rose End

Need to social distance? Our quiet country studio is far enough from Washington DC to get away without being gone. Ideal for grabbing some space, a long run, a bike ride, or visiting local wineries. The Appalachian Trail is just a stone's throw away. We respect your privacy. No smoking is allowed and internet access is from your own hot-spot. The studio includes a satellite TV, refrigerator, microwave, and coffee maker. The queen-size bed and skylight make Rose End a cozy escape.

Jun 23 – 30

G$18,430 GYD per night

Guest favorite

Apartment in Shepherdstown

4.95 out of 5 average rating, 256 reviews

1 Bedroom Apt in Historic Downtown Shepherdstown

Live like a local in our newly renovated, one-bedroom apartment in the heart of downtown Shepherdstown. Comfortably blending modern conveniences with historic charm, the 2nd floor apartment – which features space for no more than 3 guests – is located in a 100-year-old building directly behind Shepherd University's campus on German Street. Walk to the town’s restaurants, shops, and the university during Theater season, sporting events, or graduation. Comes with one free parking space.

Apr 6 – 13

G$26,659 GYD per night

Guest favorite

Apartment in Fredericksburg

4.92 out of 5 average rating, 219 reviews

Adorable 1-Bedroom Loft in Downtown Fredericksburg

Enjoy a comfortable stay in this Adorable 1-Bedroom Loft in Downtown Fredericksburg! Within walking distance to some of Fredericksburg's local favorites - Carl's Ice Cream and Mason Dixon Cafe. Curated to combine the classic beauty of Fredericksburg with modern amenities. Situated just along the Fredericksburg Canal Path - guests can enjoy the 3.1-mile paved path that provides access to just about anywhere in the city. Located within minutes of I-95 and the VRE train station.

Jun 5 – 12

G$20,070 GYD per night

Guest favorite

Apartment in Shepherdstown

4.98 out of 5 average rating, 117 reviews

The 1763 House - Stay in Downtown Shepherdstown

Welcome to our charming downtown Shepherdstown apartment, originally built in 1763 and nestled in the heart of town. Ideal for getaways, visiting family/friends, or university trips. Enjoy a spacious interior, comfortable living room, state-of-the-art kitchen, and private patio. Our downtown location on the Main Street offers convenient access to a wide selection of restaurants, unique shopping, and the Potomac river, all just a short walk away!

Oct 7 – 14

G$34,805 GYD per night