1. Comfort Inn & Suites Chestertown

- Location: Chestertown
- Guest rating: 8.6/10 (Excellent, 1000 reviews)
- Price: $96 nightly, $107 total, Dec 6 - Dec 7, Total with taxes and fees
- Review: The front desk staff were so nice, room very clean., by John
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Check prices for these dates, December 14 – 15, 2026




















Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.















The best area to stay in Still Pond is the downtown area, particularly around Main Street, for convenient access to local attractions and the waterfront.
This central area is the heart of Still Pond, offering a pleasant and walkable environment. Main Street is lined with local businesses, including shops and eateries, leading directly toward the Still Pond Creek waterfront. You'll find easy access to the public pier and views of the water from several points in this area.
For couples seeking a quiet and convenient getaway, staying in downtown Still Pond is ideal. The proximity to the waterfront allows for peaceful strolls and scenic views, and the local restaurants provide intimate dining experiences.
The best time to go to Still Pond, Maryland, is during the spring and fall seasons.
These months offer pleasant weather conditions, with comfortable temperatures and lower humidity, making it ideal for outdoor activities and exploring the natural beauty of the area. Spring (April to May) brings blooming flora and migrating birds, while fall (September to October) showcases colorful foliage.
For those interested in watersports like kayaking, fishing, or sailing on the Chesapeake Bay, late spring and early fall provide calm waters and agreeable temperatures. The milder weather also makes it great for walking or cycling along the scenic routes around Still Pond.
Travelers looking for a peaceful retreat will appreciate these shoulder seasons, as the area is generally less crowded than in the peak summer months.
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Still Pond.
Prices for hotels in Still Pond often vary, but you can find a great deal from $50 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.