Find all hotels by Red Roof Inn in Chestertown, MD from $62
Upfront pricingOur total price for your stay includes taxes and fees
Treat yourselfSave 10% or more on over 100,000 hotels worldwide with Member PricesLearn about One Key
Be pickySearch almost a million properties worldwide
Check prices for these dates
Tonight
Oct 21 - Oct 22Tomorrow
Oct 22 - Oct 23This weekend
Oct 23 - Oct 25Next weekend
Oct 30 - Nov 1Our top choices for Chestertown Red Roof Inn
$72 nightly
$80 total
Oct 28 - Oct 29
Total with taxes and fees
$55 nightly
$62 total
Oct 22 - Oct 23
Total with taxes and fees
$71 nightly
$80 total
Oct 25 - Oct 26
Total with taxes and fees
4. Red Roof Inn Baltimore South - Glen Burnie
Red Roof Inn Baltimore South - Glen BurnieFerndale
Charles
$77 nightly
$88 total
Oct 25 - Oct 26
Total with taxes and fees
Save an average of 15% on thousands of hotels when you're signed in
Top Chestertown Hotel Reviews
Hampton Inn & Suites Edgewood/Aberdeen-South
10/10 Excellent
"The rooms very clean and accommodating. Definitely will stay there again when we travel through."
Hilton Garden Inn Baltimore/White Marsh
10/10 Excellent
"Everything was excellent with the room and staff. What I didn’t like is à la carte menu Other than that I was pleased with my stay"
WoodSpring Suites Baltimore White Marsh - Nottingham
8/10 Good
"WiFi was not working"
Annapolis Waterfront Hotel, Autograph Collection
10/10 Excellent
"Great location, hotel super clean and good restaraunt . Short walking distance to great shopping and many more bars and restaraunts"
Fairfield Inn & Suites by Marriott White Marsh
10/10 Excellent
"Great location"
The Inn at Chesapeake Bay Beach Club
10/10 Excellent
"Wonderful staff! Had a problem getting into the bed because it was too high and I was too short. They were wonderful with accommodating my needs! They moved me to a new room and location!"
Comfort Inn & Suites Chestertown
10/10 Excellent
"Property was quiet and clean and close to town."
Pendry Baltimore
10/10 Excellent
"⭐️⭐️⭐️⭐️⭐️ A Beautiful Anniversary Getaway at the Sagamore Pendry Baltimore! Our anniversary stay at the Sagamore Pendry Baltimore was nothing short of amazing! From the moment we arrived, we felt welcomed and appreciated. The room upgrade was an unexpected treat and truly elevated our experience. Between the breathtaking harbor views, spacious accommodations, and beautiful atmosphere, every detail made our celebration feel extra special. Breakfast at the restaurant was absolutely delicious, and the staff was incredibly friendly, attentive, and welcoming. Their warm hospitality made an already wonderful stay even more memorable. We thoroughly enjoyed every moment of our visit. The Pendry provided the perfect setting to relax, celebrate our love, and create beautiful anniversary memories. We look forward to returning and would highly recommend this hotel to anyone looking for a luxurious and memorable getaway!"
Hampton Inn Baltimore/Glen Burnie
8/10 Good
"na"
Explore a world of travel with Expedia
- Best Western Hotels in Centreville
- Inner Harbor Hotels
- Marriott Hotels & Resorts in Abingdon
- Independent Hotels in Georgetown
- La Quinta Inn & Suites Hotels in Betterton
- Hilton Hotels in Henderson
- Resorts & Hotels with Spas in Chestertown
- Best Western Hotels in Price
- Marriott Hotels & Resorts in Grasonville
- La Quinta Inn & Suites Hotels in Chestertown
- B&B in Chestertown
- Aberdeen Hotels
- Motel 6 Hotels in Baltimore
- Hilton Hotels in Edgemere
- Romantic Hotels in Chestertown
- Best Western Hotels in Queenstown
- Downtown Baltimore Hotels
- Hotels with an Indoor Pool in Chestertown
- Extended Stay Hotels in Chestertown
- La Quinta Inn & Suites Hotels in Edgewood
- Apartments in Chestertown
- Cabin Rentals in Maryland
- Marriott Hotels & Resorts in Queenstown
- Washington Hotels
- Hotels near Washington College
- Motel 6 Hotels in Edgewood
- Beach Hotels in Chestertown
- Chestertown Hotels
- Oceanfront Hotels in Annapolis
- Cheap Hotels in Baltimore
- Pet-Friendly Hotels in Chestertown
- Oceanfront Hotels in Chestertown
- All-Inclusive Resorts in Maryland
- Maryland Hotels
- Best Western Hotels in Aberdeen Proving Ground
- Marriott Hotels & Resorts in Bowleys Quarters
- Best Western Hotels in Templeville
- Hilton Hotels in Rock Hall
- La Quinta Inn & Suites Hotels in Abingdon
- Best Western Hotels in Aberdeen
- Red Roof Inn Hotels in Joppatowne
- Baltimore Hotels
- Annapolis Hotels
- Cheap Hotels in Chestertown
- Marriott Hotels & Resorts in Stevensville
- Cabin Rentals in Chestertown
- Best Western Hotels in Edgemere
- Hotels with Free Airport Shuttle in Baltimore
- Wyndham Hotels in Earleville
- White Marsh Hotels
- Wyndham Hotels in Aberdeen
- Marriott Hotels & Resorts in Baltimore
- Luxury Hotels in Chestertown
- Hilton Hotels in Aberdeen
- Extended Stay America Hotels in Great Oak Landing
- Hotels near Baltimore Washington Intl. Thurgood Marshall
- Best Western Hotels in Chestertown
- Independent Hotels in Fairlee
- Flights from Dallas (DFW) to Baltimore (BWI)
- Flights from Atlanta (ATL) to Baltimore (BWI)
- Flights from Houston (IAH) to Baltimore (BWI)
- Flights from Charlotte (CLT) to Baltimore (BWI)
- Flights from Portland (PDX) to Baltimore (BWI)
- Flights from Tampa (TPA) to Baltimore (BWI)
- Flights from San Francisco (SFO) to Baltimore (BWI)
- Flights from Baltimore Washington Intl. Thurgood Marshall
- Flights to Maryland
- Flights from Minneapolis (MSP) to Baltimore (BWI)
- Flights from San Diego (SAN) to Baltimore (BWI)
- Flights from Phoenix (PHX) to Baltimore (BWI)
- Flights to Baltimore
- Flights from Raleigh (RDU) to Baltimore (BWI)
- Flights from Seattle (SEA) to Baltimore (BWI)
- Flights from Chicago (ORD) to Baltimore (BWI)
- Flights from Los Angeles (LAX) to Baltimore (BWI)
- Flights from Honolulu (HNL) to Baltimore (BWI)
- Flights from Las Vegas (LAS) to Baltimore (BWI)
- Flights from Orlando (MCO) to Baltimore (BWI)
- Flights from Denver (DEN) to Baltimore (BWI)
- Flights to Chestertown
- Flights to Washington
- Flights from New York (JFK) to Baltimore (BWI)
- Flights from Fort Lauderdale (FLL) to Baltimore (BWI)
- Flights from Boston (BOS) to Baltimore (BWI)
- Flights from Austin (AUS) to Baltimore (BWI)
- Flights from Miami (MIA) to Baltimore (BWI)
- Flights from Detroit (DTW) to Baltimore (BWI)