Hotels in Chestertown, Maryland

  • Overview

    Chestertown is a charming town located in Maryland, United States of America. Situated on the banks of the Chester River, this historic town offers a picturesque setting with its tree-lined streets and beautiful waterfront. Known for its rich heritage and welcoming atmosphere, Chestertown is a popular destination for history buffs, nature lovers, and those seeking a peaceful retreat.

  • When to visit

    The best time to visit Chestertown is during the spring and fall seasons when the weather is mild and pleasant. Spring brings blooming flowers and lush greenery, while fall offers picturesque foliage and comfortable temperatures. Additionally, several events and festivals take place during these seasons, bringing the town to life with vibrant colors and cultural celebrations.

  • Reasons to Visit

    There are many reasons to visit Chestertown. The town's historical significance is evident in its well-preserved architecture and landmarks, such as the Chestertown Historic District. Visitors can explore the numerous museums, art galleries, and cultural centers to learn about the town's past. Nature enthusiasts can enjoy kayaking or boating on the Chester River, while birdwatchers can spot a variety of bird species at the Eastern Neck National Wildlife Refuge. The town's vibrant arts scene, lively festivals, and delicious local cuisine also make it a compelling destination.

  • Nearby Attractions

  • Chestertown Historic District

    Explore the town's well-preserved historic district, featuring beautiful architecture and charming streets adorned with colonial-era buildings.

  • Eastern Neck National Wildlife Refuge

    Discover the diverse wildlife and stunning natural beauty of Eastern Neck Island, which is home to a variety of bird species and offers scenic trails for hiking and birdwatching.

  • Chestertown Farmers Market

    Visit the lively farmers market where you can find fresh local produce, baked goods, artisanal crafts, and enjoy the vibrant atmosphere.

  • The Mainstay

    Experience live music performances, from jazz to classical, at this renowned intimate venue known for its exceptional acoustics and welcoming ambiance.

  • Chestertown RiverArts

    Immerse yourself in the vibrant arts scene of the town, featuring exhibitions, workshops, and galleries showcasing the works of local and regional artists.

  • Hotels

  • Brampton 1860

    - Brampton 1860 in Chestertown provides adults-only accommodation with a garden, a terrace and a shared lounge. Featuring a concierge service, this property also provides guests with a picnic area. Ther Next available price is on . Brampton 1860

  • Comfort Inn & Suites Chestertown

    - Make yourself at home in one of the 81 guestrooms featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and satellite programming is availabl Next available price is 122.55 on Sept. 14, 2025. Comfort Inn & Suites Chestertown

  • Driftwood Inn

    - Make yourself at home in one of the 28 guestrooms featuring refrigerators and microwaves. Complimentary wireless internet access keeps you connected, and satellite programming is available for your en Next available price is on . Driftwood Inn

  • Red Roof Inn & Suites Chestertown

    - Make yourself at home in one of the 53 air-conditioned rooms featuring microwaves and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is avai Next available price is on . Red Roof Inn & Suites Chestertown
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4 hotels in Chestertown