Explore top 2025 5 Star Hotels in Southern Maryland

Name: The Inn at Tacaro Estate
Rating: 9.2

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Top Southern Maryland 5 Star hotels

Swanendele Inn at St. Mary's Maryland

49946 Airedele Rd, Ridge, MD

$305 nightly

$339 total

Oct 15 - Oct 16

Total with taxes and fees

This luxury bed & breakfast's private beach and marina are among the highlights. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. ...

9.8/10 Exceptional! (32 reviews)

Very beautiful clean Inn

"Very beautiful Inn. The rooms are very clean and quiet. There are lots of sitting areas on the property, and a pier that you can walk out on to view the bay. The breakfast was wonderful. There is a small bar downstairs, but we weren't sure if it was in operation. The check-in was a bit awkward. Hotels.com ..."

Reviewed on Sep 15, 2025

The Inn at Tacaro Estate

6220 Town Point Rd, Tracys Landing, MD

$477 nightly

$544 total

Oct 19 - Oct 20

Total with taxes and fees

This bed & breakfast features a seasonal outdoor pool and a hot tub. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free ...

9.2/10 Wonderful! (10 reviews)

"Amazing, warm, gracious setting. Can’t wait to return"

Reviewed on Aug 18, 2025

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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.

Southern Maryland Resorts & 5 Star Hotels

Looking for your own little slice of heaven during your next trip? Check out all the best 5-star hotels in Southern Maryland to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the 5-star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Southern Maryland 5-star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5-star hotels in Southern Maryland before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.