Where to stay

in Chestertown

We'd like to help you find something that's a great fit for your trip.

Chestertown is well-liked for its coffeehouses, lake views, and seafood restaurants. If you're interested in spending some time outdoors, Loon Lake Beach and Friends Lake are some top places to check out. Loon Lake and Hudson River are also a few notable stops. Whether you're looking to stay right in the heart of town or you're interested in a more secluded spot, we'd like to help you find a great place in Chestertown.

Top places to stay in Chestertown with breakfast

The Loft at The Remington is a B&B with free breakfast and free parking. The Fern Lodge is a B&B with free breakfast and free WiFi. It's located a short 5-minute walk from Friends Lake.

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Top romantic accommodations in Chestertown

Friends Lake Inn is a 4-star hotel featuring a full-service spa and wedding services. The property gets good marks for its helpful staff. The Fern Lodge is a 3.5-star B&B featuring 8 spa tubs and in-room massages. It's located a short 5-minute walk from Friends Lake.

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Top rated places to stay in Chestertown for families

The Fern Lodge is a B&B featuring free parking and free breakfast.

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Top rated places to stay for luxury travelers

Friends Lake Inn is a 4-star hotel featuring a full-service spa and a terrace that guests like for its helpful staff.

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Top places to stay for budget travelers in Chestertown

Pine Tree Motel & Cabins is a 2-star property good for budget-minded travelers, featuring free WiFi and free parking. Travelers like its prime location and helpful staff. It's located a short 11-minute walk from Loon Lake Beach.

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