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Check availability on Annapolis Luxury Hotels

Our top choices for Annapolis luxury hotels

Room, 2 Queen Beds, Balcony | Premium bedding, down duvets, pillow-top beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
Historic District
8.8 out of 10, Excellent, (881)
"Great location, nice and clean "
United States
Micah
The price is ₹16,003
₹18,243 total
includes taxes & fees
16 Dec - 17 Dec
Annapolis Waterfront Hotel, Autograph Collection
View from property
The Westin Annapolis

The Westin Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1000)
"Spectacular "
United States
Dennis
The price is ₹13,842
₹15,780 total
includes taxes & fees
14 Dec - 15 Dec
The Westin Annapolis
View from property
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1002)
"Very nice hotel. The dog park could have better lighting. "
United States
Andrew
The price is ₹11,791
₹13,442 total
includes taxes & fees
21 Dec - 22 Dec
Graduate by Hilton Annapolis
Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1014)
"Great place!"
United States
Tawnya
The price is ₹6,870
₹7,831 total
includes taxes & fees
28 Dec - 29 Dec
DoubleTree by Hilton Hotel Annapolis
Front of property
The Oaks Waterfront

The Oaks Waterfront

4.0 star property
Easton
10.0 out of 10, Exceptional, (41)
"Loved the Oaks! Fabulous accommodations and excellent staff"
United States
Barbara
The price is ₹37,212
₹40,933 total
includes taxes & fees
11 Dec - 12 Dec
The Oaks Waterfront
Full-sized fridge, blender, toaster oven, waffler maker
Legacy Villa

Legacy Villa

4.0 star property
Upper Marlboro
The price is ₹25,454
₹28,763 total
includes taxes & fees
24 Dec - 25 Dec
Legacy Villa
Breakfast, lunch, dinner served; sea views
Inn at Perry Cabin

Inn at Perry Cabin

5.0 star property
St. Michaels
9.6 out of 10, Exceptional, (371)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is ₹47,022
₹56,896 total
includes taxes & fees
11 Dec - 12 Dec
Inn at Perry Cabin
Horse riding
The Inn at Tacaro Estate

The Inn at Tacaro Estate

5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (11)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
The Inn at Tacaro Estate
Front of property – evening/night
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4.0 star property
Stevensville
9.4 out of 10, Exceptional, (429)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
The price is ₹16,561
₹20,674 total
includes taxes & fees
14 Dec - 15 Dec
The Inn at Chesapeake Bay Beach Club
Exterior
Pendry Baltimore

Pendry Baltimore

5.0 star property
Fells Point
9.4 out of 10, Exceptional, (1001)
"Super nice hotel in the best part of downtown Baltimore. Will definitely stay again"
United States
Melissa
The price is ₹29,546
₹38,422 total
includes taxes & fees
4 Jan - 5 Jan 2026
Pendry Baltimore
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
"Clean hotel, solid breakfast, and great staff. Beds are comfortable and rooms are up to date and quiet."
Paul 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Annapolis, MD

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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 Thurgood Marshall Memorial, Maryland State House and William Paca House. If you have a little extra time during your trip, you might want to check out Annapolis City Dock and Ego Alley.