Find luxury hotels in Chestertown, MD

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Top Chestertown Luxury Hotels

Driftwood Inn

2.0 star property
Chestertown
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • 24/7 front desk
5.2 out of 10, (175)
Sound-insulated sanctuaries feature refrigerators and premium entertainment channels in this impeccably maintained establishment. Positioned within walking distance of Washington College and local arts venues, guests appreciate the 24-hour front desk service and peaceful atmosphere.
Driftwood Inn
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.

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Find out more about Chestertown

Chestertownand its attractions for luxury travelers

Chestertown, Maryland, offers a blend of historical charm and modern luxury that appeals to travelers. Begin your exploration at the historic Chestertown Waterfront, where you can enjoy a leisurely stroll along the banks of the Chester River, savoring the picturesque views and perhaps even catching a glimpse of a local sailboat regatta. For art enthusiasts, the Kent County Arts Council hosts a variety of galleries and exhibits showcasing regional talents, providing an enriching cultural experience. Families will delight in a visit to the nearby Chesapeake Bay Maritime Museum, where interactive exhibits and stunning waterfront views make for a captivating day out. Golf aficionados can tee off at the elegant Chester River Yacht & Country Club, which features a beautifully manicured course and offers stunning vistas of the river and surrounding countryside. After a day of exploration, unwind in one of Chestertown's luxurious accommodations, such as the historic Brampton Inn, which boasts beautifully appointed rooms and lush gardens, or The Imperial Hotel, where you’ll experience attentive service and gourmet dining. Staying in the heart of Chestertown not only provides convenient access to these attractions but also allows you to immerse yourself in the town's rich heritage and warm hospitality.

Find the best luxury hotels and resorts in Chestertown

For those seeking a luxurious escape in Chestertown, Maryland, these exceptional hotels offer an indulgent experience with top amenities and stunning surroundings.

The Lodge at Great Oak Landing

  • Why it's great for a luxury retreat: The Lodge at Great Oak Landing is a perfect choice for luxury travelers looking to unwind in a serene environment, a solid guest review rating of 8.2. Guests can indulge in exclusive amenities like an onsite golf course, perfect for both enthusiasts and beginners. The hotel's direct access to a private beach and waterfront site elevates the luxury experience, allowing travelers to relax by the water or enjoy water sports at their leisure.
  • Other amenities: In addition to its top-tier golf offerings, The Lodge features a shared secured pool with sun loungers and umbrellas for ultimate relaxation. Guests can take advantage of 24-hour fitness facilities to maintain their workout routines, or enjoy the stunning marina views from their furnished balconies. The hotel also offers a sandy beach area, beach volleyball, and family-friendly playgrounds, ensuring an engaging stay for all. Self-parking is available, providing convenience for travelers with their own vehicles.
  • Nearby attractions: Kinnairds Point Drive - 12.16 miles, Still Pond Station Park - 15.25 miles

Top Chestertown Hotel Reviews

Frequently asked questions

Are you searching for the perfect hotel for your luxury trip to Chestertown?
Use Expedia to help you arrange a flight to Baltimore, MD (MTN-Martin State) airport or Easton, MD (ESN-Easton - Newnam) airport, and then choose from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you need to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Chestertown offers. During your visit, you might want to enjoy the university which Chestertown is known for.
When can I expect good weather in Chestertown?
Planning for the weather is an important factor for making your trip to Chestertown a success, especially when you're splurging. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What's there to see and do in Chestertown?
When you're in Chestertown, enjoy exploring the sights and attractions here including Historical Society of Kent County Maryland, Chestertown Historic District, and Rolphs Wharf Marina. If you have extra time while you're in the area, you might want to see Northern Chesapeake Bay and Chesapeake Bay.

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