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
Sep 6 - Sep 7Tomorrow
Sep 7 - Sep 8Next weekend
Sep 11 - Sep 13In two weeks
Sep 18 - Sep 20Our top choices for Chestertown Red Roof Inn
$72 nightly
$80 total
Sep 13 - Sep 14
Total with taxes and fees
$55 nightly
$62 total
Sep 7 - Sep 8
Total with taxes and fees
$71 nightly
$80 total
Sep 10 - Sep 11
Total with taxes and fees
$85 nightly
$96 total
Sep 10 - Sep 11
Total with taxes and fees
Save an average of 15% on thousands of hotels when you're signed in
Top Chestertown Hotel Reviews
Historic Inns of Annapolis
8/10 Good
"Fantastic location. Clean room with comfortable beds and powerful AC. Liked the history of the building. We were able to consistently get parking on the street near the hotel, which was great. The only real con was that we discovered upon reaching our room that we didn't have an exterior window--our two "windows" looked over the covered event area, which had pretty lights but was nonetheless an interior hallway, so no outside view. There were also a couple hiccups with the bathroom, one being that the glass shelf was falling down, and the other being that we were consistently given two towels even though we had four people on the reservation. But overall we were happy with our stay and appreciated being in a historic building in such a great location."
Hampton Inn Baltimore/White Marsh
10/10 Excellent
"Absolutely beautiful and the staff is amazing 💜💜. Rooms are clean , breakfast is a great selection. Close to stores"
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
10/10 Excellent
"This hotel was actually better than I expected. Check-in was quick and easy. Lots of parking. My room on the 5th floor was spacious and super clean. The beds and pillows were great! The breakfast buffet was adequate. Overall, a good stay and I’d stay there again.,"
Red Roof Inn & Suites Chestertown
10/10 Excellent
"Vending machines were out of order, only ice machine was on first floor. Otherwise it was as expected for a red roof inn and last minute booking. Our neighbors had 4 young children that were very loud and running up and down the hallway when I first arrived but they were surprisingly calm later that evening so wasn’t an issue. Over all stay was fine and I accomplished what I came there for. Breakfast would be a huge plus and of they reopened the pool that’s been closed since Covid would certainly make for a much better review. Staff was amazing as always. Friendly and accommodating."
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
8/10 Good
"Front desk pleasant and helpful, but… no accessible rooms available. Also, only non pet room available (even though reservations were made) was on 2nd floor and elevator out of service. Room itself was clean. Breakfast was good."
Best Western Kent Narrows Inn
8/10 Good
"A little out of date"
Hyatt Place Kent Narrows & Marina
10/10 Excellent
"Great location, very clean and staff were welcoming and helpful!"
Best Western Plus Hotel & Conference Center
10/10 Excellent
"Multiple Elevators were out of service and had longer wait for available one to use. Buttons seemed to not work in that one elevator that was working and light kept going out for the floor I needed to be and kept stopping one floor below instead. But staff were so kind and friendly. Very helpful staff with information in area, shuttle information and very welcoming. I did enjoy staying and if coming to Baltimore again, I will choose to stay here again. Hope the elevator will be in good condition by the time I go back."
The Lodge at Great Oak Landing
10/10 Excellent
"Gem of a local place on the water. The rooms are big and the beds are soooo comfy. The pool is cute and the beach has bands on weekends. There are gas grills and a decent restaurant. It's not fancy (for fancy stay at the manor next door). But it's not corporate either. It's authentic, peaceful and fun."
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)