Hotels with an Indoor Pool in
Chestertown

Photo by Assya A

Check Last Minute Chestertown Hotel Deals

Tonight Nov 23 - Nov 24Next weekend Nov 29 - Dec 1

Featured Chestertown Hotels with an Indoor Pool

Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD
The price is $118 per night from Dec 15 to Dec 16
$118
includes taxes & fees
Dec 15 - Dec 16
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2 out of 5
160 Scheeler Rd, Chestertown, MD
The price is $83 per night from Dec 1 to Dec 2
$83
includes taxes & fees
Dec 1 - Dec 2
Red Roof Inn & Suites 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.

Hotels in Chestertown

Maryland is a city that has a lot going on, but you have your sights set on Chestertown. This part of town is perfect for what you want to be doing, and that is everything that is not on everyone’s radar. For all that Chestertown has going on, you’ll still need a place to crash, eventually. But you don’t want any old shack, you need something that fits the trip. We have a slew of Chestertown hotels that will do the trick.

A beautiful day in the neighborhood

As much as you like getting out there, it’s also good to know a part of Maryland so well you’ll be telling the tourists where to go. Make friends with the concierge or be bold and chat up a local. It’s your trip, so choose your own adventure. And when you get in at night, you’ll have a comfy room and plenty of amenities to help you settle in. Call a friend and spin tales from the Chestertown underground. What’s a journey without a good story to go with it?

Beyond the block

We’re not talking about the Chestertown city block. We’re talking about looking beyond that block of hotels you always focus on. We give you tons of ways to sort our stash of Chestertown cheap hotels. And if you feel like living a little, but not killing your vacation vibes, choose the Hotwire Hot Rate deal. Filter by:

  • Hotwire Hot Rate: Snag some of the best hotels in Chestertown at an almost too good to be true rate. After you book, we’ll reveal the name of the hotel. You can get a luxury hotel at a budget price.
  • Price: You have a price in mind, and we have solutions. Hotels start as low as $83
  • Amenities: Rooftop lounge, designer furniture, 24-7 room service, and everything else you look for to live it up large.

Find the Chestertown hotel you want, book it, and never look back. Because your great escape is ahead of you.