Apartment vacation rentals in Winchester

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Top-rated apartment rentals in Winchester

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Guest favourite

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

$134 CAD per night

Guest favourite

Apartment in Winchester

4.87 out of 5 average rating, 154 reviews

Downtown FUN! Personal Mid Century 2bd Apartment!

Welcome to Blossom! Your own, private pied-à-terre, located in Winchester's historic district, 1 block from the Old Town Walking Mall! Blossom's UBER-LUX upgrades include a fully-stocked custom kitchen, marble countertops, new stainless steel appliances, high speed internet, gleaming hardwood floors, queen size canopy beds, heavenly memory foam mattresses, 50' smart TV, all delivered with a Euro MCM flare! Blossom is ideal for a romantic getaway, smart business travel, or a quick City escape!

Nov. 27 – Dec. 4

$208 CAD per night

Guest favourite

Apartment in Winchester

5.0 out of 5 average rating, 139 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

$270 CAD per night

Guest favourite

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.

Sep. 5 – 12

$180 CAD per night

Guest favourite

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

$274 CAD per night

Guest favourite

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

Oct. 25 – Nov. 1

$165 CAD per night

Guest favourite

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

$148 CAD per night

Guest favourite

Apartment in Culpeper

4.98 out of 5 average rating, 148 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

$182 CAD per night

Guest favourite

Apartment in The Plains

4.98 out of 5 average rating, 451 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.

Aug. 16 – 23

$129 CAD per night

Guest favourite

Apartment in Shepherdstown

4.97 out of 5 average rating, 156 reviews

Downtown Luxe Apt: Pet Friendly & Fenced Courtyard

Welcome to our warm and modern one-bedroom apartment, just steps away from history, dining, the great outdoors, and Shepherd University campus! Enjoy the convenience of street front access while enjoying a clean and private space away from the downtown bustle. Additionally, we offer a large shared fenced-in courtyard, providing a secure and spacious area for your furry friend to play. This is the perfect place to relax and unwind, and experience the historic charm of Shepherdstown.

Jun. 30 – Jul. 7

$249 CAD per night

Guest favourite

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.

Jul. 16 – 23

$157 CAD per night

Guest favourite

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!

Jun. 26 – Jul. 3

$269 CAD per night