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Historic Hotels in Chestertown

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Featured Chestertown Historic Hotels

Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2 out of 5
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews.
Red Roof Inn & Suites Chestertown
See all 1,022 properties in Chestertown
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.

Historic Hotels in Chestertown

If you’re looking for your Chestertown getaway to go down in history as the best vacay ever, you’ve got some noteworthy options to consider when it comes to where to stay. You could book a legendary or even luxury historic hotel for your trip with opulent extras. You’re probably thinking you’ll have to spend monumental money for a stately historical spot, but you may want to keep a fainting couch nearby—you’ll be shocked by what you can get for less gold bullion than you expected. Or modern cash. Whatever’s on hand.

Historically Great Spots

If you’re looking to do some R & R at one of the top historic hotels in America and don’t want to blow a stack of Benjamins while you’re at it, you’re in luck—you can stay at some of the best historic hotels in Chestertown by booking a Hotwire Hot Rate hotel deal, even if you’re historically short on time. In fact, you could save up to 60% versus booking a listed rate two weeks earlier, so locking down that 4-star place at a 2-star price is no historic feat.

A Little Mystery in Your History

You can get way more than you bargained for when you book a Hotwire Hot Rate historic hotel deal in Chestertown instead of just booking any old hotel for your trip. Not only can you get a deal for the history books when you reserve a Hot Rate, you can filter hotels by what matters most to you for your last-minute Chestertown getaway, including price, amenities, and reviews.

Frequently Asked Questions About Historic Hotels

What is a historic hotel like in Chestertown?

Looking to take in the legendary sights and sounds of the Chestertown historic district? There’s no better way to truly immerse yourself than with a stay at one of Chestertown’s historic inns and hotels. (And if you’re really lucky, that immersion includes a hot bath in a clawfoot tub.) Go ahead and save while you soak and book a Hotwire Hot Rate historic hotel deal.

How much is a hotel room at a historic hotel?

You may think you’ll have to pay a pretty penny for a historic last-minute hotel. Or just let history repeat itself by settling for a cheap hotel when you get to Chestertown, 222. But thanks to Hotwire Hot Rates, you can score a fantastic historic hotel for way less cash, even at the last minute. You could be staying at the best historic hotels in Chestertown for as low as $83. A win for the ages.

What is the difference between a historic hotel and a traditional hotel?

Historic hotels are at least 50 years old and often feature sweeping architecture and ambience. Some of the most historic hotels of the world have even been designated as historic landmarks. Staying in one of these storied spots in Chestertown is sure to give you an extra layer of interest for your vacay tales.