Apartment holiday rentals in Winchester

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Top-rated apartment rentals in Winchester

Guests agree: these apartments are highly rated for location, cleanliness and more.

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Guest favourite

Flat in Downtown Frederick

4.93 out of 5 average rating, 102 reviews

Charming Historic Downtown Apartment…The Fox’s Den

Guests will love this beautifully renovated downtown apartment, which features all the modern amenities while retaining its historic charm! Over 1,650 square feet of living area and a large outdoor deck off the master bedroom to enjoy in the warmer months. Walking distance to the wonderful downtown Frederick shops and restaurants and the award winning Carroll Creek Linear Park (don't miss the holiday-themed boats during the winter months) and only a short drive to hiking, parks and wineries!

Guest favourite

Flat in Harrisonburg

4.91 out of 5 average rating, 740 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).

Superhost

Flat in McGaheysville

4.84 out of 5 average rating, 252 reviews

Massanutten Cozy Condo with Hot Tub & Jacuzzi

Luxury Apartment ideal for families with little kids in Massanutten. There is a huge deck with private 5-person Hot Tub and small playground on it. It is located only 5 minutes away from the ski lodge, go karts, bumping cars, Mini Golf.The Campfire Grill Restaurant is only 2 minutes away. The indoor and outdoor Water park is 8 minutes away. A gorgeous and spacious retreat in the best location for skiing/snowboarding, exploring the resort, hiking, relaxing, and enjoying the fresh mountain air.

Top guest favourite

Flat in Winchester

5 out of 5 average rating, 202 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.

Superhost

Flat in Harpers Ferry

4.79 out of 5 average rating, 141 reviews

Best location! The Pullman Apt @ historic 1799 Inn

Immerse yourself in rich history while you relax in your comfy, one-bedroom apartment with kitchenette in the 2nd oldest building in town. The perfect location if you're cycling the C&O, hiking the AT, or coming by train. And you'll be just steps from historic Lower Town Harpers Ferry. The Harpers Ferry train station is just across the street. A 2-minute walk brings you to the scenic confluence of the Potomac and Shenandoah rivers as well as Harpers Ferry National Park and John Browns Fort.

Top guest favourite

Flat in Winchester

4.97 out of 5 average rating, 273 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 favourite

Flat in Shepherdstown

4.96 out of 5 average rating, 137 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 favourite

Flat in Shepherdstown

4.94 out of 5 average rating, 323 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

Superhost

Flat in Berkeley Springs

4.88 out of 5 average rating, 107 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

Top guest favourite

Flat in Shepherdstown

4.95 out of 5 average rating, 345 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 favourite

Flat in Cumberland

4.98 out of 5 average rating, 220 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 favourite

Flat in Woodstock

4.87 out of 5 average rating, 569 reviews

Heart of Town-Pet Friendly

This apartment is in a older home located in heart of town. Walking distance to Resturants, Brewhouse, Shops, Theatre, and town events, Location is great. I have my business in this house on lower level. The apartment has it's own entrance. It has 3 rooms and a bath. I love this house and want to share it. Think you will love it too.