Find hotels in Chestertown, MD from $80

Comfort Inn & Suites Chestertown is a favorite property for Expedia customers. This hotel offers free breakfast and free parking. Red Roof Inn & Suites Chestertown is another top choice for your stay based on reviews. See all available top hotels, or vacation rentals in Chestertown.

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town: Visitors give good reviews to this Chestertown vacation home rental, which is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a garden and a selection of games. Some other homes for rent in Chestertown include Charming Chestertown Waterfront Cottage and Quaint cottage with amazing sunset views to soak up nature. See all vacation rentals in Chestertown.

If it is a challenge to find properties with enhanced cleaning that have all the amenities you're looking for, consider Home2 Suites by Hilton Baltimore/White Marsh, which is a 3-star hotel located 22 miles from the city center. If you're looking for a wallet-friendly option, Comfort Inn & Suites Chestertown is a 2.5-star hotel in Chestertown that offers enhanced cleaning measures. And for a luxurious stay, consider Royal Sonesta Harbor Court Baltimore, a 4.5-star hotel that provides enhanced cleaning and is located within 30 miles of Chestertown. For more options to choose from, browse all hotels in Chestertown with enhanced sanitizing practices.

Yes, most hotel bookings are fully refundable as long as you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, you may still be able to cancel and get a refund within a 24-hour period of your booking. Filter your search by free cancellation to find flexible hotel deals in Chestertown.

For more details about rescheduling or cancelling your trip to Chestertown, click here.

Based on reviews, Red Roof Inn & Suites Chestertown is a popular 2-star hotel for our travelers looking for an economical choice, and features free WiFi and free parking. Another top choice for your budget-friendly stay is Driftwood Inn. View all budget hotels in Chestertown.

Driftwood Inn is a property with free parking and free WiFi, and it's a top choice on Expedia for families. Red Roof Inn & Suites Chestertown is another good choice for your kid-friendly vacation. Attractions in the area like Paul Reed Smith Guitars are also fun for the whole family. Find more child-friendly accommodations in Chestertown.

Red Roof Inn & Suites Chestertown is a favorite hotel for couples, and features free WiFi and free parking. See all romantic hotels in Chestertown.

Driftwood Inn is a top property for people traveling with their pets, and offers free WiFi for its human guests. Comfort Inn & Suites Chestertown is another good choice for a stay with your pet. See more pet-friendly hotel accommodations in Chestertown.

Adjacent to Washington College, Driftwood Inn is one of the top choices for your stay based on our traveler data, and this property offers free parking and free WiFi. Other good options close by include Comfort Inn & Suites Chestertown and Red Roof Inn & Suites Chestertown.

One of the top choices for your stay is Comfort Inn & Suites Chestertown, located 4.1 mi (6.6 km) from Rolphs Wharf Marina, and this hotel offers free breakfast and free parking. Driftwood Inn and Red Roof Inn & Suites Chestertown are two other good options within a few miles.

Great Oak Manor is a top 3.5-star B&B located on the beach. See more stays near the beach in Chestertown.