Hotels with smoking rooms inChestertown
Featured Chestertown Hotels with smoking rooms

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 $70
- 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.
Top Booked Hotels in Chestertown
- Comfort Inn & Suites Chestertown
- Historic Inns of Annapolis
- La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
- Sagamore Pendry Baltimore
- Quality Inn & Suites Bel Air I-95 Exit 77A
- Hilton Garden Inn Baltimore/White Marsh
- Hampton Inn Baltimore Bayview Campus
- Best Western Plus Hotel & Conference Center
- Annapolis Waterfront Hotel, Autograph Collection
- La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
- Americas Best Value Inn Edgewood
- Fairfield Inn & Suites by Marriott White Marsh
- Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
- The Inn at Henderson's Wharf, Ascend Hotel Collection
Hotels by Star Rating
More Hotel Options in Chestertown
- Hotels with Free Parking in Chestertown
- Romantic Hotels in Chestertown
- Family Hotels in Chestertown
- Pet-friendly Hotels in Chestertown
- Beach Hotels in Chestertown
- Hotels with a Pool in Chestertown
- Apartment Hotel in Chestertown
- Historic Hotels in Chestertown
- Hotel Wedding Venues in Chestertown
- Hotels with an Indoor Pool in Chestertown
- Resorts & Hotels with Spas in Chestertown
- Oceanfront Hotels in Chestertown
- Luxury Hotels in Chestertown
Top Attractions in Chestertown
- Hotels near Washington College
- Hotels near Rolphs Wharf Marina
- Hotels near River Arts Chestertown
- Hotels near Historical Society of Kent County Maryland
- Hotels near Garfield Center for the Arts at the Prince Theater
- Hotels near Wilmer Park
- Hotels near Crumpton Auction
- Hotels near Baltimore Cruise Terminal
- Hotels near U.S. Naval Academy
- Hotels near Ripken Stadium
- Hotels near Chesapeake Bay Bridge
- Hotels near Annapolis City Dock
- Hotels near Sandy Point State Park
- Hotels near White Marsh Mall
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Susquehanna River
- Hotels near Fort McHenry
- Hotels near Harford Community College
- Hotels near Cedar Lane Regional Park
Cities near Chestertown
- Annapolis Hotels
- Dover Hotels
- St. Michaels Hotels
- Delaware Beaches Hotels
- Perryville Hotels
- Edgewood Hotels
- Grasonville Hotels
- Havre De Grace Hotels
- Aberdeen Hotels
- Easton Hotels
- Bel Air Hotels
- Glen Burnie Hotels
- Chesapeake Bay Hotels
- Elkton Hotels
- Stevensville Hotels
- Rosedale Hotels
- Eastern Shore Hotels
- White Marsh Hotels
- Middletown Hotels
- North East Hotels
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