Compare and book 5 Star hotels in Southern Maryland, Maryland

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Check availability on Southern Maryland 5 Star Hotels

Tonight
29 Apr - 30 Apr
Tomorrow
30 Apr - 1 May
This weekend
1 May - 3 May
Next weekend
8 May - 10 May

Our top choices for Southern Maryland 5-star hotels

Seasonal outdoor pool, pool umbrellas, pool loungers

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful place to stay with a breathtaking view of the Chesapeake Bay from a hilltop. Has a speakeasy bar in the basement which takes you back to the 1920’s. Breakfast is very subperb!"
United States
Philip
The price is 8.152.724 ₫
9.294.253 ₫ total
includes taxes & fees
6 May - 7 May
The Inn at Tacaro Estate
Reception

Swanendele Inn at St. Mary's Maryland

Swanendele Inn at St. Mary's Maryland
5.0 star property
Ridge
9.8 out of 10, Exceptional, (32 reviews)
"A beautiful stay with amazing hosts!"
United States
Vineet
The price is 14.819.062 ₫
16.449.160 ₫ total
includes taxes & fees
1 May - 2 May
Swanendele Inn at St. Mary's Maryland
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Southern Maryland.
Gaylord National Resort & Convention Center

Gaylord National Resort & Convention Center

201 Waterfront Street Fort Washington MD
The price is 6.085.695 ₫ per night from 29 May to 30 May
6.085.695 ₫
7.935.115 ₫ total
29 May - 30 May
includes taxes & fees
8.8/10 Excellent! (1,020 reviews)
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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.

Learn more about Southern Maryland

Explore the family-friendly area of Southern Maryland—a scenic waterfront, sports teams and sights from Budds Motorcross Speedway to Maryland International Raceway.

See all hotels in Southern Maryland
Photo by Meg Faller
Open Photo by Meg Faller

Top Southern Maryland Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Southern Maryland?
The amount you pay for a 5-star hotel in Southern Maryland can vary depending on when you decide to travel and how long you plan to stay, among a range of factors. Use our price per night filter and other search tools to find the best deal on an indulgent stay.

  • Search for the lowest price per night from 4.252.306 ₫

What makes a hotel 5 stars in Southern Maryland?
Exemplary guest service is the defining feature of every 5-star hotel in Southern Maryland. From the minute you step through the door, staff cater to your every need, whether answering room service calls 24/7 or providing a turn-down service. Additionally, hotels have to offer superior conveniences to qualify for a 5-star rating. These can include luxury bathrooms, an on-site spa, swimming pools, gourmet kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Southern Maryland?
Use our filter tool to find a luxury getaway in Southern Maryland where most of what you need is included in the price. Next, narrow your results for properties that have 5 stars and are deemed "All inclusive." The main thing to look forward to at these stays? Pure indulgence and relaxation.