Apartment vacation rentals in Winchester

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Top-rated apartment rentals in Winchester

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Guest favorite

Rental unit in Harrisonburg

4.92 out of 5 average rating, 713 reviews

Restful Hilltop Apartment: No cleaning fees!

Our place is close to Family-friendly activities, art and culture, restaurants and dining, the mountains with scenic views and stimulating hiking trails, caverns and caves, the Shenandoah River, historical centers, parks. You’ll love our place because of the friendly people, the backyard with ponds and patios, the quiet neighborhood, the comfortable beds, the close proximity to town, and hilltop views. Our place is good for couples, solo adventurers, business travelers and families (with kids).

Guest favorite

Rental unit in Winchester

5 out of 5 average rating, 175 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.

Guest favorite

Rental unit in Winchester

4.97 out of 5 average rating, 250 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.

Guest favorite

Rental unit in Shepherdstown

4.97 out of 5 average rating, 123 reviews

Downtown Modern 2BR step from dining and shopping

Welcome to a modern and conveniently located two-bedroom apartment in the heart of Shepherdstown. Whether you're planning a weekend getaway or visiting the university, this apartment offers a perfect escape for your trip. Inside, you'll find a thoughtfully designed space with a coffee bar, a cozy living room, a versatile work/play room, high-speed internet, and a state-of-the-art kitchen. Explore downtown and discover a wide variety of dining options, shopping, and recreation activities.

Guest favorite

Rental unit in Shepherdstown

4.94 out of 5 average rating, 300 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.

Guest favorite

Rental unit in Berkeley Springs

4.9 out of 5 average rating, 105 reviews

1 Bedroom Apartment in Downtown Berkeley Springs

LOCATION! Enjoy easy access to everything from this perfectly located second floor apartment. This cozy apartment is a wonderful home away from home featuring many amenities. Separate Bedroom with Queen bed and walk-in closet Living Room with loveseat, chair, tv, end tables, coffee table, sofa table Free parking WiFi Full Kitchen with appliances, dishes, utensils, pots and pans Keurig Coffee Toaster Table and Chairs Bath with Single shower Washer and Dryer Small Porch Sitting Area

Superhost

Rental unit in Confluence

4.84 out of 5 average rating, 267 reviews

Turkeyfoot riverview apartment.

The Most scenic view of what George Washington referred to as The Turkeyfoot, the confluence of three rivers. Newly remodeled, this apartment has a second story balcony that probably has the best view in Confluence. Great for sitting out with your morning cup of coffee or a nice glass of wine in the evening. Kitchen is fully operational with all of the necessities. Totally private no shared spaces. There is a common area with hammocks and a fire pit.

Guest favorite

Rental unit in Shepherdstown

4.95 out of 5 average rating, 313 reviews

Downtown: Explore Shepherdstown from cozy 1br apartment

Welcome to our cozy and modern one-bedroom apartment, located just steps away from history, dining options, the beautiful outdoors, and Shepherd University campus! You'll enjoy the convenience of being right on the street while still having a peaceful and private escape from the downtown hustle and bustle. Nestled in downtown Shepherdstown, easily explore downtown, while also being a short walk away from the Potomac River.

Guest favorite

Rental unit in Cumberland

4.98 out of 5 average rating, 203 reviews

Allegheny Suite in Corner Tavern Residences

Nestled above Corner Tavern & Cafe in historic downtown, this newly renovated modern apartment supplies you with all the comforts of home in a tasteful design. Our location provides all the benefits of a night out of town, located in historic downtown, above a tavern & cafe, you'll find food, drink & maybe even music in a few short steps from your apartment.

Guest favorite

Rental unit in Gettysburg

4.9 out of 5 average rating, 145 reviews

Historic Downtown The Red Door- 1st floor

Located in the heart of historic downtown Gettysburg, our apartment is just steps away from popular and historic restaurants, wineries, ice cream, shops, ghost tours, museums, and the battlefield. In addition, we’re located 2 1/2 blocks to the town square, 3 1/2 blocks to the Majestic theatre, and about 5 blocks to the Gettysburg College.

Superhost

Rental unit in Rockwood

4.89 out of 5 average rating, 496 reviews

Taking reservations *Newly Renovated* GORGEOUS!

This newly renovated apartment is situated in Rockwood's town center. It has a kitchen to please any chef and the perfect layout to relax and unwind. You may be in town from biking the Great Allegheny Passageway, Skiing at Seven Springs/Hidden Valley, Touring Flight 93, or maybe just to visit family. We can't wait for you to stay here!

Superhost

Rental unit in Front Royal

4.93 out of 5 average rating, 120 reviews

Private apartment near center city

Second floor Apt has one bedrm The one bedrm is a Queen Bed , full kitchen, living room, 65 inch tv, free WiFi, four TVs and private enclosed screen porch, No smoking. Window A/C units. Apt is 800 sq ft. I'm onsite down stairs usually working. Pets under 45 pounds only. will provide crate for fur baby’s. Only two small pets