Hotels in Winchester, Elkton

  • Overview

    Winchester is a charming town located in Maryland, United States of America. Situated near the Pennsylvania border, Winchester offers a mix of scenic beauty and historical significance. The town's historic downtown district is filled with well-preserved buildings dating back to the 18th and 19th centuries, creating a unique and nostalgic atmosphere for visitors. The surrounding area is known for its picturesque landscapes, with rolling hills, lush farmland, and charming small towns.

  • When to visit

    The best time to visit Winchester is during the spring or fall seasons, when the weather is mild and the surrounding landscapes showcase their natural beauty. Springtime brings blooming flowers and lush greenery, while the fall foliage creates a breathtaking display of colors. The summer months are also popular for outdoor activities and festivals, but can be quite hot and humid. Winter in Winchester can be chilly, but it offers a cozy atmosphere with holiday festivities and opportunities for winter sports.

  • Reasons to Visit

    There are plenty of reasons to visit Winchester. History enthusiasts can explore the town's rich heritage by visiting the numerous historic sites and museums, including the George Washington's Office Museum and Stonewall Jackson's Headquarters Museum. Winchester is also a haven for nature lovers, with nearby nature preserves and parks offering opportunities for hiking, biking, and wildlife spotting. Additionally, the town boasts a vibrant arts and culture scene, with galleries, theaters, and live music performances taking place throughout the year.

  • Nearby Attractions

  • George Washington's Office Museum

    Step back in time and explore the recreated office of George Washington, the first President of the United States. Learn about his Revolutionary War experiences and his role in shaping American history.

  • Stonewall Jackson's Headquarters Museum

    Discover the historic headquarters of Confederate General Thomas J. 'Stonewall' Jackson during the American Civil War. The museum showcases artifacts, exhibits, and stories from this pivotal era.

  • Winchester Nature Preserve

    Immerse yourself in the natural beauty of Winchester by visiting the Winchester Nature Preserve. This sanctuary offers hiking trails, birdwatching opportunities, and scenic picnic spots amidst diverse flora and fauna.

  • Old Town Winchester

    Explore the quaint streets of Old Town Winchester, filled with charming shops, restaurants, and historic buildings. Enjoy a leisurely stroll and soak in the ambiance of this delightful downtown area.

  • Museum of the Shenandoah Valley

    Experience the art, history, and culture of the Shenandoah Valley region at this comprehensive museum. Discover a vast collection of artworks, decorative arts, and explore the beautiful gardens.

  • Hotels

  • Best Western Chesapeake Bay North Inn

    - Make yourself at home in one of the 80 air-conditioned rooms featuring refrigerators and microwaves. Wireless internet access (surcharge) keeps you connected, and cable programming is available for yo Next available price is 227.05 on Sept. 19, 2025. Best Western Chesapeake Bay North Inn

  • Comfort Inn and Suites

    - Make yourself at home in one of the 91 guestrooms featuring refrigerators and microwaves. LCD televisions with cable programming provide entertainment, while complimentary wireless internet access kee Next available price is 198.53 on Sept. 20, 2025. Comfort Inn and Suites

  • Hampton Inn Elkton

    - Make yourself at home in one of the 71 guestrooms featuring refrigerators and LCD televisions. Your pillowtop bed comes with premium bedding. Complimentary wired and wireless internet access keeps you Next available price is on . Hampton Inn Elkton

  • Holiday Inn Express & Suites Elkton - University Area, an IHG Hotel

    - Make yourself at home in one of the 82 guestrooms featuring refrigerators and microwaves. Wired and wireless internet access is complimentary, and flat-screen televisions with cable programming provid Next available price is 169.29 on Sept. 19, 2025. Holiday Inn Express & Suites Elkton - University Area, an IHG Hotel

  • Holiday Inn Express North East, an IHG Hotel

    - Make yourself at home in one of the 71 air-conditioned rooms featuring refrigerators and microwaves. Wired and wireless internet access is complimentary, and flat-screen televisions with satellite pro Next available price is 256.86 on Sept. 19, 2025. Holiday Inn Express North East, an IHG Hotel

  • La Quinta Inn & Suites by Wyndham Newark - Elkton

    - Make yourself at home in one of the 70 air-conditioned rooms featuring refrigerators and microwaves. Your pillowtop bed comes with premium bedding, and all rooms are furnished with sofa beds. Wired an Next available price is on . La Quinta Inn & Suites by Wyndham Newark - Elkton

  • Red Carpet Inn

    - Make yourself at home in one of the 59 air-conditioned rooms featuring microwaves. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment Next available price is on . Red Carpet Inn

  • Sutton Inn

    - Located within 40 km of Delaware Museum of Natural History and 13 km of Dayett Station, Sutton Inn offers rooms in Elkton. With free WiFi, this 3-star hotel offers a shared lounge and room service. Th Next available price is on . Sutton Inn
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  2. North America
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  5. Cecil County
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8 hotels in Winchester