Explore 1 Luxury Hotels in Chestertown

Name: Pendry Baltimore
Price range: $441 total
Rating: 9.2

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Best Luxury Hotels in Chestertown

Driftwood Inn

609 Washington Avenue Chestertown MD

$64 nightly

$70 total

Dec 24 - Dec 25

Total with taxes and fees

Free self parking is available and the motel's front desk is staffed around-the-clock. WiFi in public areas is free. Express check-in and express check-out are ...

5/10 (175 reviews)

Rooms are clean, staf was helpful

Reviewed on Aug 18, 2025

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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.

5 star hotels in Chestertown

Pendry Baltimore

1715 Thames St. Baltimore MD

$375 nightly

$441 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

9.2/10 Wonderful! (1,001 reviews)

Chestertown Luxury Hotels

Do you want to stay at an elegant 5 star hotel for your next getaway? Do you want to be pampered like royalty? When you're ready, the Chestertown luxury hotels are the plush oasis you’ve been looking for.

Choose from the best luxury hotels in Chestertown to make your stay as comfortable and memorable as possible. Deluxe amenities await you upon check-in—perks like a heated pool, luxurious spa, and 24-hour reception service will cater to your every need, no matter the hour. If you’re tired from the day’s activities and don’t feel like wandering around to look for a meal, sit down to dinner at one of the high-end restaurants on property or contact room service for a sophisticated dining experience in the comfort of your own suite. Getting to and from the airport will be an easy task as well because most of these fancy hotels offer a free shuttle service for easy transportation.

We want you to enjoy your next vacation in style and the top luxury resorts in Chestertown will help you do just that. Browse Travelocity right now to find amazing deals on the best luxury hotels and 4 star hotels in Chestertown, and plan your next opulent escape.