Hillsmere Shores
Travel Guide
Visit Hillsmere Shores
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
The price is CA $137 per night from Oct 1 to Oct 2
CA $137
CA $156 total
Oct 1 - Oct 2
includes taxes & fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.8/10 Excellent! (1,208 reviews)
"The beds were comfortable. Amenities were plentiful. Enjoyed the stay. The shuttle driver John was great, and friendly. Would come back again."
Reviewed on Sep 28, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
The price is CA $150 per night from Oct 12 to Oct 13
CA $150
CA $220 total
Oct 12 - Oct 13
includes taxes & fees
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (2,024 reviews)
"Pretty outdated for the price. Shower was terribly small and basic . Walls super thin. Could hear a phone conversation word for word in the room next to ours ."
Reviewed on Sep 28, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
The price is CA $156 per night from Oct 4 to Oct 5
CA $156
CA $177 total
Oct 4 - Oct 5
includes taxes & fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
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.
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Annapolis MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Annapolis City Dock and Bay Ridge Beach are ...
9.6/10 Exceptional! (19 reviews)
"We had a lovely stay at this charming cottage on the bay. Everything was well maintained, the host provided strong communication, the grounds are beautiful, and our family found the hot tub to be a wonderful place to both relax amidst nature and reconnect . Also our 2 little dogs felt very much at ..."
Reviewed on Aug 3, 2026
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Saint Michaels MD
Stay at this cottage in St. Michaels. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina ...
9.6/10 Exceptional! (134 reviews)
"Location was perfect and we enjoyed the sunrise every morning. Walkable to everything in St. Michael’s. Beautiful historic home and furnishings. A great stay!!"
Reviewed on Aug 24, 2026
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Rock Hall MD
Book a stay at this family-friendly villa in Rock Hall. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Rock Hall Harbor and The Mainstay ...
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.
Things to do
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
CA $13
per traveller
80% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
CA $36
per adult
100% of travellers recommend
Best of Annapolis Tour: Colonial, State House, Naval Academy
CA $48
per adult
