Find Romantic Hotels in Annapolis, MD

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Pick from 19 Annapolis Romantic Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

The Westin Annapolis
Exterior
The Westin Annapolis
4.0 star property
8.6 out of 10, Excellent, (1000)
"Great experience overall!"
The price is SAR 653
SAR 745 total
includes taxes & fees
20 Dec - 21 Dec
The Westin Annapolis
Kent Island Resort
Exterior
Kent Island Resort
3.5 star property
9.2 out of 10, Wonderful, (89)
"Wonderful stay, charming inn. "
The price is SAR 629
SAR 836 total
includes taxes & fees
1 Dec - 2 Dec
Kent Island Resort
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
Kent Island Beach House:Winter, Spring, Summer & Fall there is something for All
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
10.0 out of 10, Exceptional, (75)
"We were on Kent Island for a family reunion. This property comfortably accommodated our group of 6 adults and 4 children ages 10-16 (3 families). The bedrooms were large enough and spread out enough to allow for privacy and quiet spots. The volleyball court was a big hit with everyone. There were many games and additional game equipment available. Great weekend. Thank you. This is a second rental we have made with Donna and will be back again."
The price is SAR 2,628
SAR 4,545 total
includes taxes & fees
24 Nov - 25 Nov
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
Historic Inns of Annapolis
Exterior
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1695)
"Love the hotel and stay here when I’m in town. Very happy to see the key system replaced, the old system was terrible. The WiFi still a bit slow for business and the room has no updated USB-C charging, no wireless charging and no clock. The staff is exceptional and that matters most!"
The price is SAR 392
SAR 571 total
includes taxes & fees
24 Nov - 25 Nov
Historic Inns of Annapolis
The Inn at Chesapeake Bay Beach Club
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club
4.0 star property
9.4 out of 10, Exceptional, (367)
"It is a beaty!"
The price is SAR 785
SAR 967 total
includes taxes & fees
22 Dec - 23 Dec
The Inn at Chesapeake Bay Beach Club
Hilton Garden Inn Annapolis Downtown
Exterior
Hilton Garden Inn Annapolis Downtown
3.0 star property
8.6 out of 10, Excellent, (982)
"The staff was outstanding; couldn’t have been more helpful. Enjoyed the hotel restaurant several times. Tha room was large and well appointed. The bathroom was good size with a nice walk-in shower."
The price is SAR 380
SAR 433 total
includes taxes & fees
15 Dec - 16 Dec
Hilton Garden Inn Annapolis Downtown
Graduate by Hilton Annapolis
Reception
Graduate by Hilton Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1001)
"Very smooth checkin. The property is in a great location and is very clean. "
The price is SAR 549
SAR 626 total
includes taxes & fees
18 Dec - 19 Dec
Graduate by Hilton Annapolis
Best Western Annapolis
Exterior
Best Western Annapolis
2.5 star property
7.8 out of 10, Good, (1001)
"Great breakfast. "
The price is SAR 304
SAR 347 total
includes taxes & fees
28 Nov - 29 Nov
Best Western Annapolis
Crowne Plaza Annapolis, an IHG Hotel
Exterior
Crowne Plaza Annapolis, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (1001)
"I had a relaxing and enjoyable stay. The breakfast was delicious."
The price is SAR 386
SAR 440 total
includes taxes & fees
25 Nov - 26 Nov
Crowne Plaza Annapolis, an IHG Hotel
Annapolis Waterfront Hotel, Autograph Collection
Exterior
Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
8.8 out of 10, Excellent, (776)
"All good "
The price is SAR 808
SAR 921 total
includes taxes & fees
2 Dec - 3 Dec
Annapolis Waterfront Hotel, Autograph Collection
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.
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Frequently asked questions

Searching for romantic hotels in Annapolis?
If you and your partner need some romantic time away, we’d like to help you plan for it. Couples choose Annapolis for its top-notch restaurants, major shopping area, and interesting historical sites. If you want to spend some time strolling through captivating scenery with your love, you might make a visit to Maryland Quiet Waters Park, Sandy Point State Park, or Ellen O. Moyer Nature Park at Back Creek. Whether you’d like to soak in a spa tub or get a couples’ massage, you’ll be sure to find accommodation in Annapolis to make for a relaxing weekend away.
How many romantic hotels will we be able to find in Annapolis?
Expedia has 7 romantic Annapolis hotels for you both to enjoy.
When is the best time of year for a romantic getaway to Annapolis?
If you’re hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Annapolis: The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Annapolis is 52 inches.
What is there to do in Annapolis?
There’s nothing better than wandering around a new destination with your sweetheart, so consider checking out all that Annapolis has to offer. If you’re hoping to see some of the area’s cultural attractions, you and your partner will love Annapolis for its major shopping area and interesting historical sites. You might think about stopping by William Paca House, Annapolis City Dock, or Navy-Marine Corps Memorial Stadium while you’re seeing the sights.
What's the best way to get to Annapolis and around town during my romantic getaway?
This information about transportation options in Annapolis might help your romantic getaway go off without a hitch: To get to Annapolis, you can fly into Fort Meade, MD (FME-Tipton), which is the closest major airport, located 16.2 mi (26.1 km) from the city center. If you’d like to venture out around the area, you may want a rental car for your journey.