Hotels in Shady Side

Discover Shady Side: Where Nature's Beauty Meets Cultural Treasures

Nestled along the picturesque shores of the Chesapeake Bay, Shady Side, Maryland is a hidden gem for nature lovers and cultural explorers alike. This tranquil destination offers stunning waterfront views and access to serene natural parks, perfect for hiking, birdwatching, and picnicking. Discover the rich maritime history at local museums and enjoy fresh seafood at charming eateries. Whether you’re kayaking in the bay or strolling through vibrant landscapes, Shady Side invites you to unwind and embrace its unique blend of coastal beauty and small-town charm. Experience the allure of this off-the-beaten-path haven! For our best hotel rates in Shady Side and to enhance your stay, be sure to check out Hotels.com's Last-Minute DealsOpens in a new window on travel.

Discover great hotels in Shady Side

Shady Side, Maryland offers a variety of hotel accommodations, from cozy inns to budget-friendly options. Whether you're seeking a waterfront view or a charming local experience, you'll find welcoming guest rooms and convenient amenities to make your stay enjoyable while exploring the area's natural beauty. Here are some of our travelers' favorite hotels in Shady Side:

1. Annapolis Waterfront HotelOpens in a new window: This inviting 4.0-star hotel provides a unique blend of natural beauty and urban convenience, making it perfect for leisure travelers. Situated in the city center, it offers a rejuvenating experience with its rooftop terrace, allowing guests to immerse themselves in nature while enjoying stunning views. The hotel features well-appointed rooms that are clean and comfortable, enhancing the overall stay. Travelers appreciate its close proximity to Annapolis, making it a prime location for exploration and relaxation.
2. Inn at Perry CabinOpens in a new window: This luxurious 5.0-star hotel is an idyllic retreat for travelers seeking a high-end getaway. With exquisite service and a beautiful location, it promises an unforgettable experience. The hotel features a range of upscale amenities, including a stunning pool and fine dining options, ensuring every moment is indulgent. Guests particularly enjoy the relaxed atmosphere, where they can unwind and take in the breathtaking surroundings, making it a top choice for a serene escape.
3. The Westin AnnapolisOpens in a new window: This stylish 4.0-star hotel caters to adventure enthusiasts, offering a range of outdoor activities for a vibrant stay. With a focus on comfort and recreation, it provides access to nearby adventure sports, making it a prime destination for those looking to explore the great outdoors. The hotel features clean and comfortable accommodations, ensuring a restful night's sleep after an exhilarating day. Visitors appreciate the welcoming atmosphere and convenient location, enhancing their overall experience.

Top locations to stay in Shady Side

When visiting Shady Side, Maryland, consider staying in Eastport, Murray Hill, or the Historic District. Eastport offers vibrant nightlife and easy access to the Chesapeake Bay, while Murray Hill features charming local restaurants and parks. The Historic District immerses you in the area's rich heritage. For first-time visitors, Eastport is the best choice for its lively atmosphere and proximity to attractions.

1. EastportOpens in a new window: Eastport is a charming waterfront community where you can enjoy a laid-back atmosphere with stunning views of the Chesapeake Bay. Its proximity to Annapolis makes it a great base for exploring the area, with unique shops and local galleries that reflect the region's artistic flair. Outdoor enthusiasts will love the nearby Sandy Point State Park, perfect for hiking, picnicking, and beach activities. Plus, you can indulge in watersports like sailing and kayaking, making it a delightful stay for those who appreciate nature and scenic landscapes.
2. Murray HillOpens in a new window: Murray Hill offers a picturesque escape with its tree-lined streets and beautiful homes, providing a serene environment perfect for relaxation. This neighborhood is just a stone's throw from downtown Annapolis, where you can explore a range of cultural attractions, including art galleries and theaters. For shopping, you can easily access nearby malls, blending comfort with convenience. Murray Hill's community vibe and easy access to both urban attractions and natural beauty make it a great choice for travelers seeking a balanced experience.
3. Historic DistrictOpens in a new window: The Historic District is a must-visit for those who love history and charm. Here, cobblestone streets lead you to beautifully preserved buildings, offering a glimpse into the past. You can explore local museums and cultural sites that celebrate the area’s rich heritage. The district is also close to a variety of shops and eateries, making it easy to enjoy a leisurely stroll while sampling local flavors. Its central location allows for easy access to nearby attractions while immersing you in the unique history of the region.

Things to do in Shady Side

Shady Side beckons travelers with its lush forests, serene lakes, and picturesque coastal views. Enjoy a day of hiking scenic trails, or dive into the refreshing waters for some sea exploration. After an active day, unwind with delightful shopping options that promise a charming local vibe.

• Shadyside ParkOpens in a new window – Discover a charming urban park where you can unwind amidst nature. Enjoy walking trails, picnic areas, and the vibrant community atmosphere that invites relaxation and leisure. Perfect for an afternoon stroll or a fun family outing, Shadyside Park is a local favorite.
• Maryland Quiet Waters ParkOpens in a new window – Venture into this serene urban park and experience the beauty of nature in a tranquil setting. With winding paths, lush woodlands, and art installations, it’s an ideal spot for a peaceful escape. Bring your camera to capture the stunning landscapes and wildlife.
• Chesapeake Bay BridgeOpens in a new window – Marvel at the engineering marvel of the Chesapeake Bay Bridge. Take a drive across this modern bridge and soak in breathtaking views of the bay. Stop at designated lookout points to appreciate the scenery and snap some memorable photos.
• Triton BeachOpens in a new window – Spend a delightful day at Triton Beach, where sandy shores meet refreshing waters. Engage in sunbathing, beach games, or a leisurely swim. The beach offers a perfect retreat for families and friends to enjoy the sun and surf.
• Captain Avery MuseumOpens in a new window – Step back in time at the Captain Avery Museum, a historic house that showcases maritime history and local heritage. Explore fascinating exhibits and learn about the area’s rich past while enjoying the scenic views of the surrounding landscape.

5 tips for savvy savings when booking a hotel in Shady Side

1. Book for the cheapest times: For those looking for an affordable getaway, Shady Side is best visited in January, February, or December when hotel prices tend to be lower. To fully appreciate the area’s key landmarks, cultural sites, and natural parks, a stay of at least 2 to 3 days is recommended. This budget-friendly trip will allow you to explore fascinating museums and scenic parks, making it a great value for money experience. Prices may drop during these months, making it an ideal time for travelers on a budget.
2. Look for last-minute deals on Hotels.com: To discover last-minute deals to Shady Side, visit the DealsOpens in a new window or Last-Minute DealsOpens in a new window sections on Hotels.com, where you may find discounted rates as your travel date approaches. You could also enable email alerts or push notifications to stay updated on flash sales and exclusive promotions, helping you secure the best hotel deal. Additionally, use Smart ShoppingOpens in a new window through the app to compare room rates and amenities, allowing you to quickly identify available options and price drops, ensuring you’re primed for a spontaneous getaway.
3. Be flexible with dates: Prices can fluctuate depending on factors like the hotel's location, star rating, and the season, so being flexible with your travel dates may help you save on your stay at a hotel in Shady Side. For travelers seeking something special, boutique hotels often provide a more personalized experience and can sometimes offer better value. When you book through Hotels.com, we’ll inform you whether the price for your chosen dates is above or below the average. If the price is on the higher end, we’ll recommend more budget-friendly dates to increase your chances of getting a great deal.
4. Consider your location: Staying near major attractions or downtown areas can be convenient, but it often comes with a higher price tag. If you're looking for more budget-friendly options, consider hotels in less central neighborhoods, where you can find a better balance between cost and access to the sights you want to see. Independent hotels located a bit further out usually tend to be more affordable and can offer a more genuine experience.
5. Join One Key™: Become a One Key MemberOpens in a new window for free and book your next stay in Shady Side. Save on over 100,000 hotels worldwide with exclusive member prices. As a member, you can quickly progress through the tiers and enjoy perks, like free room upgrades when available and food and beverage discounts at select VIP Access properties.

Best time to go to Shady Side

Shady Side experiences its lowest average temperature in January, at 35.8°F (2.1°C), while July is the hottest month, with an average temperature of 78.3°F (25.7°C). July is usually the wettest month. May to July are the peak travel months in Shady Side, attracting a higher number of tourists. During this peak period, the weather is mostly sunny, with light rainfall. On the other hand, October to December tend to be quieter times to visit, marked by light rainfall and mostly sunny conditions.