We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
The latest reviews. The lowest prices. The perfect place to shop for hotels.

Hotels near Chesapeake Sailing School

  • Sort by:
  • Traveler Ranked
  • Lowest Price
  • Distance
TripAdvisor members only.
Login for exclusive access to hotel deals up to 40% off
Login to get best prices
Sponsored
174 West St, Annapolis, MD 21401-2824
1.6 miles from Chesapeake Sailing School
#9 of 21 hotels in Annapolis
Top Deal
$159*
$135* /night
View Deal
TripAdvisor
$135*
Expedia.com
$159*
Booking.com
$135*
View all 13 deals 
80 Compromise St, Annapolis, MD 21401-1810
1.0 miles from Chesapeake Sailing School
#5 of 21 hotels in Annapolis
Top Deal
$326*
$242* /night
View Deal
TripAdvisor
$242*
Hotwire.com
$242*
HotelQuickly
$326*
View all 11 deals 
58 State Cir, Annapolis, MD 21401-1906
1.4 miles from Chesapeake Sailing School
#1 of 21 hotels in Annapolis
Top Deal
$169*
$111* /night
View Deal
Travelocity
$164*
Hotels.com
$164*
Booking.com
$169*
View all 12 deals 
126 West St, Annapolis, MD 21401-2802
1.6 miles from Chesapeake Sailing School
#2 of 21 hotels in Annapolis
Top Deal
$189*
$169* /night
View Deal
TripAdvisor
$169*
Loews Hotels
$189*
Hotels.com
$169*
View all 13 deals 
174 West St, Annapolis, MD 21401-2824
1.6 miles from Chesapeake Sailing School
#9 of 21 hotels in Annapolis
Top Deal
$159*
$135* /night
View Deal
TripAdvisor
$135*
Expedia.com
$159*
Booking.com
$135*
View all 13 deals 
201 West Bay St, Cape Saint Claire, MD 21401
1.6 miles from Chesapeake Sailing School
No photo provided
100 Westgate Cir, Annapolis, MD 21401-3379
1.8 miles from Chesapeake Sailing School
#7 of 21 hotels in Annapolis
$193* /night
View Deal
TripAdvisor
$193*
Hotels.com
$193*
Priceline
$193*
View all 9 deals 
2451 Riva Rd, Annapolis, MD 21401-7025
3.7 miles from Chesapeake Sailing School
#12 of 21 hotels in Annapolis
Top Deal
$138*
$101* /night
View Deal
TripAdvisor
$101*
Hotwire.com
$101*
HotelQuickly
$138*
View all 15 deals 
1 Womack Dr, Annapolis, MD 21401-7372
3.9 miles from Chesapeake Sailing School
#18 of 21 hotels in Annapolis
$90* /night
View Deal
TripAdvisor
$90*
Expedia.com
$90*
Travelocity
$90*
View all 11 deals 
189 Admiral Cochrane Dr, Annapolis, MD 21401-7307
4.0 miles from Chesapeake Sailing School
#3 of 21 hotels in Annapolis
$139* /night
View Deal
TripAdvisor
$139*
SpringHill Suites
$139*
Expedia.com
$139*
View all 13 deals 
124 Womack Dr, Annapolis, MD 21401-7399
4.0 miles from Chesapeake Sailing School
#10 of 21 hotels in Annapolis
Top Deal
$149*
$124* /night
View Deal
TripAdvisor
$129*
Travelocity
$149*
Expedia.com
$149*
View all 14 deals 
173 Jennifer Rd, Annapolis, MD 21401-3043
4.0 miles from Chesapeake Sailing School
#15 of 21 hotels in Annapolis
$95* /night
View Deal
TripAdvisor
$95*
Booking.com
$95*
Priceline
$95*
View all 12 deals 
210 Holiday Ct, Annapolis, MD 21401-7001
4.1 miles from Chesapeake Sailing School
#6 of 21 hotels in Annapolis
Top Deal
$177*
$153* /night
View Deal
TripAdvisor
$159*
Doubletree.com
$159*
Cancelon
$177*
View all 14 deals 
170 Admiral Cochrane Dr, Annapolis, MD 21401-7308
4.1 miles from Chesapeake Sailing School
#13 of 21 hotels in Annapolis
Top Deal
$139*
$119* /night
View Deal
TripAdvisor
$119*
Expedia.com
$139*
Hotels.com
$139*
View all 9 deals 
120 Admiral Cochrane Dr, Annapolis, MD 21401-7308
4.1 miles from Chesapeake Sailing School
#16 of 21 hotels in Annapolis
$95* /night
View Deal
TripAdvisor
$95*
Hotels.com
$95*
Booking.com
$95*
View all 12 deals 
2520 Riva Road, Annapolis, MD 21401-7405
4.1 miles from Chesapeake Sailing School
#17 of 21 hotels in Annapolis
Top Deal
$109*
$73* /night
View Deal
TripAdvisor
$76*
Priceline
$76*
HotelQuickly
$109*
View all 14 deals 
2559 Riva Rd, Annapolis, MD 21401-7401
4.2 miles from Chesapeake Sailing School
#11 of 21 hotels in Annapolis
$124* /night
View Deal
TripAdvisor
$124*
Expedia.com
$124*
Booking.com
$124*
View all 9 deals 
Sponsored
8330 Corporate Dr, Landover, MD 20785-2234
20.8 miles from Chesapeake Sailing School
$169* /night
View Deal
TripAdvisor
$169*
Expedia.com
$169*
Travelocity
$169*
View all 11 deals 
69 Old Mill Bottom Rd N, Annapolis, MD 21409-5431
4.2 miles from Chesapeake Sailing School
#21 of 21 hotels in Annapolis
Top Deal
$72*
$67* /night
View Deal
Booking.com
$72*
Priceline
$72*
Expedia.com
$70*
View all 10 deals 
305 Harry S Truman Pkwy, Annapolis, MD 21401-7481
4.3 miles from Chesapeake Sailing School
#8 of 21 hotels in Annapolis
Top Deal
$136*
$112* /night
View Deal
TripAdvisor
$116*
Hotels.com
$116*
Elvoline
$136*
View all 14 deals 
76 Old Mill Bottom Rd N, Annapolis, MD 21409-5418
4.3 miles from Chesapeake Sailing School
#14 of 21 hotels in Annapolis
Top Deal
$133*
$109* /night
View Deal
TripAdvisor
$109*
Expedia.com
$109*
HotelQuickly
$133*
View all 13 deals 
74 Old Mill Bottom Rd N, Hwy 50 Exit 28, Annapolis, MD 21409-5418
4.3 miles from Chesapeake Sailing School
#19 of 21 hotels in Annapolis
Top Deal
$62*
$59* /night
View Deal
TripAdvisor
$59*
Booking.com
$59*
HotelsClick
$62*
View all 11 deals 
2600 Housley Rd, Annapolis, MD 21401-7009
4.6 miles from Chesapeake Sailing School
#4 of 21 hotels in Annapolis
$119* /night
View Deal
TripAdvisor
$119*
Priceline
$119*
Country Inns
$119*
View all 13 deals