A historic town street at dusk with a prominent church dome, brick buildings, and a yellow fire hydrant.

Search Luxury Hotels in Annapolis

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Annapolis Luxury Hotels

Tonight
20 Sept - 21 Sept
Tomorrow
21 Sept - 22 Sept
Next weekend
25 Sept - 27 Sept
In two weeks
2 Oct - 4 Oct

Our top choices for Annapolis luxury hotels

Premium bedding, down duvets, pillow-top beds, in-room safe
View from property
Room, 1 King Bed | Premium bedding, down duvets, pillow-top beds, in-room safe
Room, 1 King Bed | Premium bedding, down duvets, pillow-top beds, in-room safe

1. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
₹22,167
₹25,270 total
includes taxes & fees
4 Oct - 5 Oct
Annapolis Waterfront Hotel, Autograph Collection
Lobby
Property amenity
Lobby
Bar (on property)

2. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Historic district hotel blends Beaux Arts elegance with spa luxury, featuring lavish treatments near Annapolis attractions.
₹17,162
₹19,565 total
includes taxes & fees
27 Sept - 28 Sept
The Westin Annapolis
View from property
Lobby
Lobby
Bar (on property)

3. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
  • Upscale Annapolis retreat offers nautical elegance with Egyptian cotton linens and pillowtop beds.
₹14,259
₹16,255 total
includes taxes & fees
27 Sept - 28 Sept
Graduate by Hilton Annapolis
Reception
Lobby
Bar (on property)
Lobby

4. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
₹7,952
₹9,066 total
includes taxes & fees
27 Sept - 28 Sept
DoubleTree by Hilton Hotel Annapolis
Premium bedding, down duvets, in-room safe, desk
Suite, 1 Bedroom (Water View) | Premium bedding, down duvets, in-room safe, desk
Golf
Premium bedding, down duvets, in-room safe, desk

5. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
  • Waterfront luxury awaits with golf, spa, and marina at this St. Michaels coastal retreat.
₹57,813
₹63,595 total
includes taxes & fees
13 Oct - 14 Oct
Inn at Perry Cabin
Seasonal outdoor pool, pool umbrellas, pool loungers
Frette Italian sheets, premium bedding, down duvets, free WiFi
Interior
Luxury Suite, 1 Bedroom | Frette Italian sheets, premium bedding, down duvets, free WiFi

6. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
  • Indulge in beachside luxury at this 5-star estate featuring a seasonal outdoor pool, private balconies, and Italian Frette sheets.
₹36,506
₹41,617 total
includes taxes & fees
21 Sept - 22 Sept
The Inn at Tacaro Estate
Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen
Indoor wedding
Luxury Cottage, 1 King Bed, River View | Premium bedding, iron/ironing board, free WiFi, bed sheets
Luxury Suite, 1 Bedroom, Balcony | Balcony view

7. The Oaks Waterfront

The Oaks Waterfront
Easton
₹42,195
₹46,415 total
includes taxes & fees
23 Sept - 24 Sept
The Oaks Waterfront
5 restaurants; breakfast, lunch, dinner and brunch served
Interior
Point of interest
Couples treatment room(s), sauna, body treatments, aromatherapy

8. Four Seasons Hotel Baltimore

Four Seasons Hotel Baltimore
Harbor East
  • Indulgent waterfront retreat with 5 restaurants and a full-service spa offers a lavish Baltimore experience in Harbour East.
₹42,785
₹50,272 total
includes taxes & fees
19 Oct - 20 Oct
Four Seasons Hotel Baltimore
Exterior
Seasonal outdoor pool, pool cabanas (surcharge), pool umbrellas
Interior
Restaurant

9. Pendry Baltimore

Pendry Baltimore
Fells Point
  • Immerse in harbor-side luxury at Baltimore's Pendry hotel, where elegant relaxation meets waterfront sophistication.
₹39,213
₹50,019 total
includes taxes & fees
19 Oct - 20 Oct
Pendry Baltimore
Front of property – evening/night
Dining
Garden
Lobby sitting area

10. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
₹18,336
₹22,792 total
includes taxes & fees
19 Oct - 20 Oct
The Inn at Chesapeake Bay Beach Club
View all properties

Top Annapolis Hotel Reviews

Best Western Annapolis

Best Western Annapolis

8/10 Good
"Convenient location. Clean room. I was just there to sleep while attending the Maryland Seafood Festival. Parking was fine. Breakfast was okay. I had just spent two days pigging out on Maryland seafood. Okay for breakfast is a compliment!"
Michael 2-night trip
Posted 13 hours ago
Best Western Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Very nice property, toilet needs upgrade."
Sterling 3-night trip
Posted 14 hours ago
Crowne Plaza Annapolis by IHG
TownePlace Suites by Marriott Annapolis

TownePlace Suites by Marriott Annapolis

10/10 Excellent
"AMAZING hotel!! One of my absolute favorites!!Highly highly recommend to any & everybody!"
Crystal 1-night trip
Posted 19 hours ago
TownePlace Suites by Marriott Annapolis
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

8/10 Good
"Could do better with parking it should be inclusive for handicapped people."
Fowler 2-night trip
Posted 6 days ago
Hilton Garden Inn Annapolis Downtown
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Room was amazing. Staff is super friendly and helpful. Plenty of parking. Would definitely stay again."
Michael 2-night trip
Posted 6 days ago
Country Inn & Suites by Radisson, Annapolis, MD
Village Inn Annapolis MD

Village Inn Annapolis MD

10/10 Excellent
"very clean room. All the basic items you need from a budget motel. I admit on the outside the motel looks a bit rough, but inside the rooms where it really matters, it was clean, well organized, and comfortable. I would stay here again, if I was looking for a cheap accommodation in the Annapolis area. Despite being right next to a busy state highway, it was very quiet and conveniently located to a couple of local restaurants and a convenience store."
Keith 1-night trip
Posted 9 days ago
Village Inn Annapolis MD

Frequently asked questions

Are you searching for the perfect hotel for your luxury holiday in Annapolis?
Use Expedia and let us help you arrange a flight to Fort Meade, MD (FME-Tipton) airport or Baltimore Washington International Airport (BWI) airport, and then select from different places to stay that will deliver the luxury you want. Amenities are an important consideration when you plan a holiday, so we make it easy to find what you need to make your stay special. If you want a posh hotel that has a spa, an indoor pool or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Annapolis has to offer. While you're visiting, you might want to think about enjoying the live music and sporting events, which Annapolis is known for.
When can I expect good weather in Annapolis?
Planning for the weather is an important factor for making your trip to Annapolis a success, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 24°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Annapolis is 1318 mm.
What's there to see and do in Annapolis?
Take in some sights and attractions while you're in Annapolis by visiting Maryland State House, William Paca House and Annapolis City Dock. If you have a little extra time during your trip, you might want to check out Navy-Marine Corps Memorial Stadium and Maryland Hall for Creative Arts.

Explore a world of travel with Expedia