Romantic Hotels in Annapolis

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Oct 4 - Oct 5
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Oct 5 - Oct 6
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Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

Romantic Hotels in Annapolis

1. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
$147
$167 total
includes taxes & fees
Oct 26 - Oct 27
Graduate by Hilton Annapolis

2. The Westin Annapolis

The Westin Annapolis
Annapolis
$199
$227 total
includes taxes & fees
Oct 25 - Oct 26
The Westin Annapolis

3. 134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
Annapolis
$379
$432 total
includes taxes & fees
Oct 20 - Oct 21
134 Prince - Luxury Boutique Hotel

4. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
$129
$147 total
includes taxes & fees
Oct 25 - Oct 26
SpringHill Suites by Marriott Annapolis

5. Flag House Inn

Flag House Inn
Historic District
$218
$248 total
includes taxes & fees
Oct 6 - Oct 7
Flag House Inn

6. 86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel
Historic District
$272
$310 total
includes taxes & fees
Oct 6 - Oct 7
86 State Circle - Luxury Boutique Hotel

7. 1313 West Luxury Boutique Hotel

1313 West Luxury Boutique Hotel
Homewood
$262
$298 total
includes taxes & fees
Oct 6 - Oct 7
1313 West Luxury Boutique Hotel

8. Kent Island Resort

Kent Island Resort
Stevensville
$161
$213 total
includes taxes & fees
Oct 28 - Oct 29
Kent Island Resort

9. Courtyard by Marriott Bowie

Courtyard by Marriott Bowie
Bowie
$134
$152 total
includes taxes & fees
Oct 18 - Oct 19
Courtyard by Marriott Bowie

10. Live! Casino & Hotel Maryland

Live! Casino & Hotel Maryland
Arundel Mills
$172
$213 total
includes taxes & fees
Oct 6 - Oct 7
Live! Casino & Hotel Maryland

11. The Hotel at Arundel Preserve

The Hotel at Arundel Preserve
Arundel Mills
$144
$164 total
includes taxes & fees
Oct 11 - Oct 12
The Hotel at Arundel Preserve

12. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
$185
$204 total
includes taxes & fees
Oct 6 - Oct 7
The Tilghman Island Inn

13. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
$542
$596 total
includes taxes & fees
Nov 3 - Nov 4
Inn at Perry Cabin

14. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
$161
$178 total
includes taxes & fees
Oct 20 - Oct 21
Rod 'N' Reel Resort

15. St Michaels Inn

St Michaels Inn
St. Michaels
$99
$109 total
includes taxes & fees
Oct 6 - Oct 7
St Michaels Inn

16. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
$389
$443 total
includes taxes & fees
Nov 1 - Nov 2
The Inn at Tacaro Estate

17. Hyatt House BWI Airport Baltimore

Hyatt House BWI Airport Baltimore
Linthicum Heights
$125
$143 total
includes taxes & fees
Nov 1 - Nov 2
Hyatt House BWI Airport Baltimore

18. Hilton Baltimore BWI Airport

Hilton Baltimore BWI Airport
Linthicum Heights
$122
$139 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Baltimore BWI Airport

19. The Westin Baltimore Washington Airport - BWI

The Westin Baltimore Washington Airport - BWI
Linthicum Heights
$159
$181 total
includes taxes & fees
Oct 18 - Oct 19
The Westin Baltimore Washington Airport - BWI

20. Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center
Medford
$116
$136 total
includes taxes & fees
Oct 11 - Oct 12
Best Western Plus Hotel & Conference Center
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Top neighborhoods in Annapolis

Historic District

Discover a well-preserved historic district with elements of the original town plan, featuring landmarks like the Maryland State House, St. Ann's Church, and Paca House and Gardens. The neighborhood features prestigious educational institutions like St. John's College and the U.S. Naval Academy.

Eastport

Eastport's maritime soul comes alive through its scenic waterfront promenades along the Severn River and Back Creek. The Annapolis Maritime Museum showcases local nautical heritage while the peninsula's "Restaurant Row" buzzes with seafood spots and live music. Explore charming streets lined with historic homes or watch sailboats glide through Annapolis Harbor from public piers. Waterfront dining dominates the food scene with fresh Chesapeake Bay blue crabs and oysters taking center stage. Most visitors stay in boutique inns or bed & breakfasts housed in converted historic buildings. The neighborhood is best explored on foot, with easy access to downtown Annapolis via the Eastport Bridge.

West Annapolis

West Annapolis gives you a front-row seat to authentic Maryland living without the tourist crowds. Tree-lined streets and well-maintained colonial homes create a peaceful retreat just minutes from downtown attractions. Navy-Marine Corps Memorial Stadium sits nearby, while the neighborhood's proximity to the Severn River and College Creek offers scenic waterfront walks for nature lovers. Getting around is best done by car or on foot through this residential haven. While dining options are limited within the neighborhood itself, downtown Annapolis restaurants are just a short drive away. Travelers can find charming bed & breakfasts and vacation rentals that provide a genuine taste of local life.

Murray Hill

Murray Hill offers a peaceful retreat from downtown Annapolis with its tree-lined streets and historic charm. Colonial and Federal-style homes create a living museum of early American architecture just steps from the water. Take a leisurely stroll to nearby Spa Creek or catch a performance at the Ballet Theater of Maryland. Dining requires a quick walk to downtown's seafood spots and Chesapeake Bay specialties. Most visitors stay in charming bed & breakfasts housed in converted colonial homes with period furnishings. The neighborhood's proximity to marinas and waterfront promenades makes it perfect for travelers seeking authentic maritime history without the tourist crowds.

Hillsmere

Hillsmere offers a slice of authentic waterfront living just outside Annapolis's busy core. The community beach and marina invite you to kayak, swim, or just watch the Chesapeake Bay waters lap against the shore. Maryland Quiet Waters Park provides peaceful trails through nature, while the Great Frogs Winery offers tastings with local flavor. Tree-lined streets create a calm retreat from tourist crowds, with comfortable vacation rentals replacing typical hotels. Downtown Annapolis is just a 15-minute drive away, making this neighborhood perfect for travelers who want suburban tranquility with easy access to city attractions.

Top landmarks in Annapolis

A large building with ornate architecture, a cannon, and a sign reading "Bancroft Hall".

U.S. Naval Academy

9.4/10 (1,474 reviews)
If you'd like to get a taste of Naval Academy student life, check out U.S. Naval Academy, in the heart of the town. Why not take a stroll along the port and watch the sunset while you're here?
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A large suspension bridge over a body of water with a sandy beach in the foreground.

Chesapeake Bay Bridge

8.8/10 (1,066 reviews)
If seeing the sights is on your list of things to do, head to Chesapeake Bay Bridge— just one of the landmarks located 5.2 mi (8.3 km) from central Annapolis. Why not take a stroll along the port and watch the sunset while you're here?
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A park with a walking path, picnic tables, and a large tree. In the background, there is a bridge over a body of water.

Sandy Point State Park

8.6/10 (221 reviews)
Sandy Point State Park is 5.4 mi (8.8 km) from central Annapolis, why not stop by during your stay. Why not take a stroll along the port and watch the sunset while you're here?
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A grand hall with marble columns, a chandelier, and informational displays about historical rooms.

Maryland State House

9.0/10 (433 reviews)
Maryland State House is worth a pic or two when discovering Historic District. Why not take a stroll along the port and watch the sunset while you're here?
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Annapolis City Dock

9.4/10 (1,099 reviews)
If you want to give your credit card some exercise, head out to Annapolis City Dock in Historic District. Why not take a stroll along the port and watch the sunset while you're here?
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Navy-Marine Corps Memorial Stadium

9.2/10 (287 reviews)
You can catch an event at Navy-Marine Corps Memorial Stadium, located 0.8 mi (1.3 km) from central Annapolis. Why not take a stroll along the port and watch the sunset while you're here? If you think Navy-Marine Corps Memorial Stadium is cool, you also might like Alumni Hall and Tose Family Tennis Center, both located nearby.
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Westfield Annapolis Mall

8.8/10 (394 reviews)
If you like shopping, take time out to go to Westfield Annapolis Mall when in Parole. Why not take a stroll along the port and watch the sunset while you're here? Splash some more cash at Annapolis Mall Shopping Center.
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Maryland Renaissance Festival

10.0/10 (1 review)
If thrills are what you're after, head to Maryland Renaissance Festival, located 5.4 mi (8.6 km) from central Annapolis. If you have fun at Maryland Renaissance Festival, you'll love Maryland Hall for Creative Arts and Annapolis Bowl, both located nearby.
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