Vacation Homes in Chestertown, MD

Vacation homes in Chestertown make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.

Private Chestertown rental homes range between $90 - $1,240 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.

To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.

There are some exciting amenities available in Chestertown vacation home rentals. You might look for Chestertown rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room. 

Vacation rentals in Chestertown offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.

You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.

Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Chestertown. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Chestertown hotels and vacation homes that best suit your stay. We also have deals for flights, and Chestertown car rentals. You’ll save even more when you bundle your items into a Chestertown vacation package!

There are 483 rental homes in Chestertown. Enter your travel dates to check availability.

Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.