Name: Crowne Plaza Annapolis by IHG
Price range: $125 total
Rating: 8.8

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

$90 nightly

$103 total

Oct 4 - Oct 5

Total with taxes and 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 ...

Historic Inns of Annapolis

58 State Circle Annapolis MD

$148 nightly

$169 total

Oct 12 - Oct 13

Total with taxes and 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 ...

Crowne Plaza Annapolis by IHG

173 Jennifer Rd Annapolis MD

$110 nightly

$125 total

Oct 4 - Oct 5

Total with taxes and 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 ...

8.8/10 Excellent! (1,019 reviews)

"Pool was green and hot tub was empty. Our room's toilet seat was loose. And the first night there was no parking (we had to park in a bank parking lot) because they were hosting an event."

Reviewed on Sep 29, 2026

See all 1,231 properties in Highland Beach

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

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 ...

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

See all properties in Highland Beach

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.