Large gate with words of welcome to Old Town Winchester

Best Hotels in Winchester, VA

Nestled in Virginia’s Shenandoah Valley and an easy drive to Washington, DC, Winchester offers visitors a blend of history and modernity. Whether you’re planning a relaxing weekend getaway, a family adventure, or a business trip, finding the right place to stay is essential. In this article, you’ll read about the best hotels in Winchester, VA each with its own unique comforts and charms. 

The George Washington Grand Hotel

The stately George Washington Grand Hotel, a Wyndham property, is a perfect blend of historic charm and modern amenities. Built in 1924 and located in the heart of downtown Winchester, it’s just a short walk to all the best restaurants and shopping in town. Each room is clean and spacious, equipped with high-quality plush beds and work desks with Herman Miller® ergonomic chairs. 

In fact, the most frequent comment in the hotel’s reviews is how amazing the bed is. One reviewer said, “the bed was probably the most comfortable bed I have slept on when traveling.”

The rooftop lounge has panoramic views of Winchester and live entertainment on the weekends. The indoor pool is modeled after a Roman bathhouse and the therapeutic treatments offered by in-house Saumaj Health Spa are relaxing and revitalizing.

Price: Rooms from $159/night
Address: 103 East Piccadilly Street, Winchester, VA 22601

Hilton Garden Inn

The Hilton Garden Inn Winchester is a modern hotel with great amenities and hotel staff that reviewers rave about over and over again.

This hotel’s location makes it super easy to get where you need to go. Are you in Winchester to spend time at  Shenandoah University? The Hilton Garden Inn is only half a mile from there. In town to work from your company’s corporate offices? This hotel is particularly close to many of these local headquarters. And it’s still only 1.5 miles from historic Old Town Winchester.

Amenities include an indoor pool, and an on-site restaurant, The Garden Grille, if you’re not in the mood to go out for food. And! they have pet-friendly rooms available.

Price: Rooms from $123/night
Address: 120 Wingate Dr, Winchester, VA 22601

TownePlace Suites by Marriott Winchester

Ideal for extended stays or those seeking extra space, TownePlace Suites by Marriott Winchester offers modern apartment-style accommodations. The suites are equipped with all the comforts of home, including fully equipped kitchens and separate areas for living, working, and sleeping. Within the hotel, amenities include laundry facilities, an outdoor patio with a grill, a pool and fitness center, and a 24-hour market. Pet-friendly suites are available.

This hotel has an 8.9 rating on Booking.com! Some review highlights include compliments about the breakfast’s quality and variety, the extraordinary staff, and the generous storage space in the already large suites.

Price: Rooms from $143/night
Address: 170 Getty Ln, Winchester, VA 22602

Hampton Inn Winchester-University/Mall Area

The Hampton Inn offers guests solid amenities and a prime location near Shenandoah University and the Apple Blossom Mall. Their hot breakfast starts your day right, while complimentary Wi-Fi keeps you connected. Each room is spacious with soft, comfy bedding. Relax in the inviting indoor pool or keep up with your health goals in the fully equipped fitness center. If you’re in the mood for comfort food, explore nearby dining options serving delicious Southern cuisine.

Price: Rooms from $103/night
Address: 640 E Jubal Early Dr, Winchester, VA 22601

Country Retreats near Winchester, VA

Waypoint House Bed & Breakfast

Waypoint House Bed & Breakfast is a delightful haven for travelers seeking a charming and historic weekend getaway in Northern Virginia. This cozy B&B offers a selection of elegantly decorated rooms, each with a unique character and modern amenities. 

Guests can savor the delicious homemade breakfast made with locally sourced ingredients and enjoy warm, personalized hospitality from the innkeepers. 

The peaceful atmosphere and proximity to the Shenandoah Valley’s attractions make Waypoint House an ideal choice for couples looking for a romantic getaway, a mother-daughter weekend, or anyone seeking a relaxing country retreat.

Price: Rooms from $128/night
Address: 211 S Church St, Berryville, VA 22611
Distance from Old Town Winchester: 11 miles/20-minute drive

Hillbrook Inn

The Hillbrook Inn is an idyllic rural sanctuary located just 30 minutes from Old Town Winchester. The collection of historic cottages and the grand main house is a tapestry of rustic elegance. Each cottage tells its own story, with cozy quilts and rocking chairs on private porches, inviting you to savor sweet tea and watch the sunset.

Awaken to the rooster’s crow and then dig into the farm-to-table breakfast with fresh eggs and homemade preserves. Sit and read a book by the Inn’s serene pond, stroll the gardens, or take an easy drive into Winchester to shop, eat, drink, and be merry. And then come back to lounge in a hammock.

Price: Rooms from $232/night
Address: 4490 Summit Point Rd, Charles Town, WV 25414
Distance from Old Town Winchester: 18 miles/31-minute drive

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