Compare HOTELS, RESORTS, AND RENTALS in Chestertown, Maryland, USA
About Chestertown Vacation Rentals
There are more than 62 places to stay in Chestertown that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Chestertown.
Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Chestertown, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Chestertown. Places to stay near Chestertown are 950.86 ft² on average, with prices averaging ZA R9,279 a night.
Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Chestertown with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.
Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods Chestertown, MD
Frequently Asked Questions About Chestertown?
What are the top hotels or resorts in Chestertown?
You have a lot of choices in or near Chestertown. If you need a hotel in the Chestertown area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Chestertown:
- Comfort Inn & Suites Chestertown
- Comfort Inn & Suites Chestertown
- Red Roof Inn & Suites Chestertown
- Driftwood Inn
- Driftwood Inn
- Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
- Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
- Carriage House Hideaway in Middle of Chestertown
- Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
- Circa 1900 Home in the Heart of Historic Downtown Chestertown
How many hotels, resorts, or rentals are available in Chestertown?
At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 62 in the Chestertown area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Chestertown.
