Compare Cheap 5 Star Hotels
Secret Bargains - Save an extra 10% or more on select hotels
Get more for your budget and save up to 50% off select Secret Bargain hotels
Get even more value with CheapTickets Price Guarantee!
Change your flight without a fee on select flights
Cheap Chestertown Hotels
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
The price is $123 per night
$123
includes taxes & fees
$110 per night
Dec 24 - Dec 25
Free Cancellation
Reserve now, pay when you stay
0.64 mi from city center
When you stay at Comfort Inn & Suites Chestertown in Chestertown, you'll be in the historical district, within a 5-minute drive of Washington College and Historical Society of Kent County Maryland.
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
The price is $76 per night
$76
includes taxes & fees
$68 per night
Jan 1 - Jan 2, 2025
Free Cancellation
Reserve now, pay when you stay
0.58 mi from city center
You'll be centrally located in Chestertown with a stay at Red Roof Inn & Suites Chestertown, and 11 minutes by foot from Washington College.
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
3.92 mi from city center
Located in Chestertown, this vacation home is on the waterfront, within a 15-minute drive of Washington College and Garfield Center for the Arts at the Prince Theater.
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
The price is $214 per night
$214
includes taxes & fees
$159 per night
Dec 23 - Dec 24
27.98 mi from city center
With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.
Sagamore Pendry Baltimore
1715 Thames St., Baltimore, MD
The price is $412 per night
$412
includes taxes & fees
$351 per night
Jan 12 - Jan 13, 2025
Free Cancellation
Reserve now, pay when you stay
28.3 mi from city center
With a stay at Sagamore Pendry Baltimore in Baltimore (Fells Point), you'll be within a 5-minute drive of Johns Hopkins Hospital and National Aquarium in Baltimore.
Best Western Plus Hotel & Conference Center
5625 O'Donnell Street, Baltimore, MD
The price is $115 per night
$115
includes taxes & fees
$98 per night
Jan 5 - Jan 6, 2025
Free Cancellation
Reserve now, pay when you stay
25.92 mi from city center
With a stay at Best Western Plus Hotel & Conference Center in Baltimore (Medford), you'll be within a 10-minute drive of Baltimore Cruise Terminal and Baltimore Inner Harbor Marina.
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct, Rosedale, MD
The price is $90 per night
$90
includes taxes & fees
$78 per night
Dec 19 - Dec 20
Free Cancellation
Reserve now, pay when you stay
24.05 mi from city center
When you stay at La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh in Rosedale, you'll be in the business district, within a 15-minute drive of Baltimore Cruise Terminal and Johns Hopkins Hospital.
Quality Inn & Suites Bel Air I-95 Exit 77A
2112a Emmorton Park Road, Edgewood, MD
The price is $57 per night
$57
includes taxes & fees
$50 per night
Dec 19 - Dec 20
Free Cancellation
Reserve now, pay when you stay
20.67 mi from city center
Located in Edgewood, Quality Inn & Suites Bel Air I-95 Exit 77A is within a 10-minute drive of CopperPlex and Cedar Lane Regional Park.
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
2112b Emmorton Park Rd, Edgewood, MD
The price is $69 per night
$69
includes taxes & fees
$62 per night
Dec 30 - Dec 31
Free Cancellation
Reserve now, pay when you stay
20.67 mi from city center
Located in Edgewood, La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A is within a 15-minute drive of CopperPlex and Cedar Lane Regional Park.
La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie
6323 Ritchie Highway, Glen Burnie, MD
The price is $82 per night
$82
includes taxes & fees
$72 per night
Dec 24 - Dec 25
Free Cancellation
Reserve now, pay when you stay
29.16 mi from city center
When you stay at La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie in Glen Burnie, you'll be near the airport, within a 15-minute drive of Baltimore Cruise Terminal and Baltimore Inner Harbor Marina.
Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St, Annapolis, MD
The price is $236 per night
$236
includes taxes & fees
$207 per night
Dec 29 - Dec 30
27.95 mi from city center
With a stay at Annapolis Waterfront Hotel, Autograph Collection, you'll be centrally located in Annapolis, within a 10-minute walk of U.S. Naval Academy and William Paca House.
Hampton Inn Baltimore Bayview Campus
6571 Eastern Avenue, Baltimore, MD
The price is $129 per night
$129
includes taxes & fees
$110 per night
Dec 24 - Dec 25
Free Cancellation
Reserve now, pay when you stay
25.39 mi from city center
With a stay at Hampton Inn Baltimore Bayview Campus, you'll be centrally located in Baltimore, within a 10-minute drive of Baltimore Cruise Terminal and Baltimore Inner Harbor Marina.
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.
Often, one of the most difficult things about booking a hotel is finding the best time to go. The cost of staying in hotels in could vary significantly, depending on the time of the year chosen. If you would like to figure out the most suitable time to take a trip then using CheapTickets could be the best option for you. We will be able to provide information on hotels in to ensure that you get the best deal possible. So if you are looking for a booking website that will streamline the process and offer good prices, then log in and get booking.
Chestertown hotels essential information
Accommodation | 1,030 hotels |
|---|---|
Lowest Price | $57 |
Highest Price | $412 |
Popular hotels | Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, 350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock , Historic Inns of Annapolis, Sagamore Pendry Baltimore, Best Western Plus Hotel & Conference Center, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh, Quality Inn & Suites Bel Air I-95 Exit 77A, La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A, La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie, Annapolis Waterfront Hotel, Autograph Collection, Hampton Inn Baltimore Bayview Campus |
Most Recent Chestertown Hotel Reviews
Best Western Plus Hotel & Conference Center
5 out of 5
Posted 1 day ago
CheapTickets Verified Review
"Very nice and clean! Convenient too! The shower head could have been more adjustable. "
A verified traveler stayed at Best Western Plus Hotel & Conference Center
Types of Hotels
Top 20 Chestertown Hotels
Hotels Near Chestertown
Top Hotel Brands
Hotels By Star Rating
Cities near Chestertown
More to Explore in Chestertown
Top Picks
Hotels
Cheap Hotels in Daytona BeachCheap Hotels in AnnapolisCheap Hotels in GalvestonCheap Hotels in South Padre IslandCheap Hotels in Huntington BeachCheap Hotels in North BeachCheap Hotels in Virginia BeachCheap Hotels in Chesapeake BeachCheap Hotels in EdgewaterCheap Hotels in Gulf ShoresCheap Hotels in Palm SpringsCheap Hotels in DestinCheap Hotels in Myrtle BeachCheap Hotels in St. LeonardCheap Hotels in Folly BeachCheap Hotels in Ocean City
Flights