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Shady Side Hotels

Not Just Any Hotel – Only the Best Shady Side Hotels, Selected for You!

Shady Side
Jan 31, 2025 - Feb 01, 2025
2 adults, 1 room
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Shady Side Hotels

Discover Your Perfect Stay

Nestled along the picturesque shores of the Chesapeake Bay, Shady Side offers a charming escape from the hustle and bustle of city life. This hidden gem is not only known for its tranquil waterfront views but also for its cozy accommodations that cater to every type of traveler. Whether you’re seeking a romantic getaway, a family vacation, or a solo retreat, Shady Side MD hotels provide the perfect home base to explore this beautiful region.

When it comes to lodging, visitors will find a range of options that reflect the local charm and hospitality. From quaint bed-and-breakfasts with personalized service to larger hotels that offer modern amenities, Shady Side caters to diverse needs. After a restful night in one of these delightful hotels, you can start your day by discovering local attractions, fresh seafood eateries, and breathtaking bay views that capture the essence of Maryland's coastal charm.

In addition to comfortable accommodations, Shady Side serves as a gateway to a wealth of outdoor activities, including boating, fishing, and hiking along scenic trails. Many hotels offer packages that include outdoor adventures or partnerships with local tours, ensuring you experience the best of what this area has to offer. So, pack your bags and get ready to explore, because Shady Side MD hotels will be waiting to welcome you for an unforgettable stay.

Name of hotel Accommodation Rating Price, $
The Westin Annapolis

8.4 / 10

(200 Reviews)

 From 180US$
Holiday Inn Express & Suites Annapolis

7.5 / 10

(232 Reviews)

 From 179US$
Loews Annapolis Hotel

9.0 / 10

(1095 Reviews)

 From 128US$
8.4
Very good (200)

The Westin Annapolis

4
100 Westgate Cir
While not directly in Shady Side is one of the most luxurious choices close to the area, making it ideal for discerning travelers. Situated just a short drive away, this upscale hotel boasts contemporary rooms featuring signature Heavenly Beds, ensuring a restful night’s sleep. Guests can enjoy fine dining at the on-site restaurant, which focuses on fresh, locally sourced ingredients, complementing the luxurious experience. With a full-service spa, fitness center, and indoor pool, The Westin Annapolis offers diverse amenities for relaxation and recreation. Its proximity to Shady Side allows guests to explore the serene bay area while returning to the luxury of this premier hotel. Elevate your stay with a seamless blend of convenience and luxury at The Westin Annapolis.

From

180US$ /per night
7.5
Very good (232)

Holiday Inn Express & Suites Annapolis

3
2451 Riva Rd
The Holiday Inn Express & Suites Annapolis is an excellent option for families seeking a comfortable stay among Shady Side MD hotels. This hotel offers spacious family suites equipped with modern amenities and conveniences such as mini-fridges and microwaves. Guests will find a complimentary breakfast featuring a variety of options, perfect for fueling up before a day of exploration. The hotel's convenient location provides easy access to local attractions, including parks and the scenic Chesapeake Bay, ensuring a fun-filled itinerary for families. In addition, the property features an outdoor pool where kids can splash and play while parents relax. Experience family-friendly hospitality and comfort at the Holiday Inn Express & Suites Annapolis during your Shady Side adventure.

From

179US$ /per night

Cozy Retreats in Shady Side MD Hotels

In this section, we explore cozy retreats among the Shady Side MD hotels that offer guests a warm and welcoming atmosphere. These hotels provide a homey feel, perfect for visitors looking for a relaxing getaway surrounded by nature. With easy access to local attractions and stunning waterfront views, these cozy accommodations are ideal for couples and families alike. After your days of exploration, you can return to these inviting settings to recharge for your next adventure. Each hotel in this collection features unique charm and personalized service, making them memorable places to stay. Experience the delightful comfort that these Shady Side MD hotels have to offer.

9
Excellent (1095)

Loews Annapolis Hotel

4
126 West St
Located in the lively heart of Annapolis, the Loews Annapolis Hotel presents an ideal blend of luxury and hospitality, making it a worthy mention among Shady Side MD hotels. With spacious rooms that incorporate contemporary design, guests are treated to comfort and elegance during their visit. The hotel features a vibrant restaurant that showcases local culinary talent and seasonally inspired menus, perfect for those looking to taste the flavors of Maryland. Additionally, its proximity to the waterfront and nearby attractions allows for easy exploration while providing upscale accommodations. Known for its attentive service and exceptional amenities, the Loews Annapolis Hotel prioritizes a seamless guest experience. Enjoy a luxurious stay that connects you to both Shady Side and the broader beauty of the Chesapeake region.

From

128US$ /per night