Historic Hotels & Resorts in Annapolis from NZ$173

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Check availability on Annapolis Historic Hotels

Tonight
31 Dec - 1 Jan
Tomorrow
1 Jan - 2 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Annapolis historic hotels

Terrace/patio
Historic Inns of Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1903)
" Great place to stay!"
United States
Lewis
Historic Inns of Annapolis
Front of property
Flag House Inn

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.4 out of 10, Exceptional, (85)
"The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. "
United States
Elizabeth
The price is NZ$356
includes taxes & fees
4 Jan - 5 Jan 2026
Flag House Inn
Exterior
134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
2.5 star property
Annapolis
9.8 out of 10, Exceptional, (33)
"Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff"
United States
Ian
134 Prince - Luxury Boutique Hotel
Exterior
86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel
2.0 star property
Historic District
10.0 out of 10, Exceptional, (3)
"Amazing hotel, friendly staff, super clean and comfortable. My best hotel ever, and I have been in 100 + hotels."
Norway
Jo
The price is NZ$515
includes taxes & fees
4 Jan - 5 Jan 2026
86 State Circle - Luxury Boutique Hotel
Marina
Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (73)
"Great location!"
United States
Burton S.
The price is NZ$563
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy 2br home w/ parking in downtown Annapolis
Interior
Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
10.0 out of 10, Exceptional, (5)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is NZ$1,274
includes taxes & fees
5 Jan - 6 Jan 2026
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Fridge, microwave, oven, stovetop
2nd floor Spacious Downtown Getaway- Across from US Naval Academy

2nd floor Spacious Downtown Getaway- Across from US Naval Academy

2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Historic District
9.6 out of 10, Exceptional, (27)
"Loved this place - well appointed, convenient and great hosts ! Definitely will rent again!"
United States
betsy b.
The price is NZ$542
includes taxes & fees
4 Jan - 5 Jan 2026
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
3 bedrooms, iron/ironing board, travel cot, WiFi
★ Midcentury Modern Getaway ★ Prime Location ★

★ Midcentury Modern Getaway ★ Prime Location ★

★ Midcentury Modern Getaway ★ Prime Location ★
Historic District
10.0 out of 10, Exceptional, (35)
"Great location, well stocked for cooking and eating. Great 3rd floor deck. Very comfortable beds. Great quick communication with Ryan. "
United States
Mark T.
The price is NZ$997
includes taxes & fees
4 Jan - 5 Jan 2026
★ Midcentury Modern Getaway ★ Prime Location ★
Exterior detail
Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (16)
"Lovely, secluded cottage close to downtown Annapolis. Host was very accommodating and communicated lots of great info. Looking forward to coming back when we can stay longer."
United States
Michael C.
The price is NZ$993
includes taxes & fees
5 Jan - 6 Jan 2026
Secluded Cozy Cottage in Historic Downtown
Fridge, microwave, oven, stovetop
Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is NZ$1,250
includes taxes & fees
5 Jan - 6 Jan 2026
Historic Row Home in Downtown Annapolis
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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Top Annapolis Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Breakfast menu was great! Pool and hot tub were nice!"
Terrence 2-night trip
Posted 1 day ago
Country Inn & Suites by Radisson, Annapolis, MD

Frequently asked questions

What should a history enthusiast expect from a trip to Annapolis?
Those who want a tour of the local history will want to plan a trip to Annapolis. While you're here, you might want to visit the university campus and major shopping area. You can also relish a trip to the top-notch restaurants.
What's the best accommodation in Annapolis to be near historical sites?
Based on our travel expertise, Historic Inns of Annapolis is a top historic hotel bookable on Expedia and it features free Wi-Fi. Thurgood Marshall Memorial is a short walk away.
How many historically relevant hotels will I find in Annapolis?
Annapolis is home to 555 lodging options bookable on Expedia though you won't find many designated historic hotels.
What are the must-see historical places and other sights to visit in Annapolis?
Annapolis is notable for landmarks like William Paca House, 97, 99 and 101 East Street and Stanton School & Community Center. Cultural venues include Maryland Hall for Creative Arts, Annapolis Maritime Museum and The Colonial Players. A couple of additional sights to add to your itinerary are Thurgood Marshall Memorial and Maryland State House.
What is a historic hotel like in Annapolis?
Guests who choose historic hotels have the chance to stay in a building that has been recognised with an official historic designation. Historic hotels throughout the world can be castles, palaces or even pubs or old police stations — any building that's been identified as being of special interest. These types of hotels in Annapolis often preserve original qualities like traditional architecture and period features in their public spaces or guestrooms.
What is the difference between a historic hotel and a heritage hotel?
The two are similar. "Historic hotel" is a term often used in the US, whereas "heritage hotel" is common in Asia and Europe. Historic hotels tend to focus on the physical building and architecture. A heritage hotel draws meaning mainly from the cultural value and how it inspired the surrounding community.
Do historic hotels in Annapolis have modern facilities?
Yes, efforts are made to preserve historic facades and treasured traditions, while interiors have safety features and modern conveniences. Tourists who book a stay can expect the usual amenities from a contemporary hotel such as Smart TVs, WiFi and updated bathroom facilities. Booking a historic hotel in Annapolis doesn't mean you're picking a place that's rundown or uncomfortable for guests.