A river with boats, a marina, and a town with houses and buildings.

Find hotels in Shady Side, MD from AED 296

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Star rating

Our top choices for Shady Side hotels

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (42 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
The price is AED 1,616
AED 1,778 total
includes taxes & fees
29 Jun - 30 Jun
The Oaks Waterfront

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1,002 reviews)
"Great location, modern rooms compared to area offerings."
United States
Shruti
The price is AED 314
AED 346 total
includes taxes & fees
7 Jul - 8 Jul
St Michaels Inn

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (390 reviews)
"maybe a little overpriced but a great place to stay in St Michaels!"
United States
Michel
The price is AED 2,380
AED 2,618 total
includes taxes & fees
26 Jul - 27 Jul
Inn at Perry Cabin

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (466 reviews)
"Wonderful stay!"
United States
Rachel
The price is AED 951
AED 1,127 total
includes taxes & fees
22 Jul - 23 Jul
The Wildset

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (75 reviews)
"Mr Will very good Host and breakfast very delicious sure we will come back ❤️"
United States
MENBERE
The price is AED 744
AED 818 total
includes taxes & fees
29 Jun - 30 Jun
George Brooks House B&B

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (927 reviews)
"Room was clean and staff took very good care of us"
United States
Carol
The price is AED 367
AED 408 total
includes taxes & fees
12 Jul - 13 Jul
Quality Inn Grasonville near Kent Island

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,002 reviews)
"The hotel was clean and looked nice, the bed was very soft in the middle and uncomfortable and the $14 breakfast was no where near worth it."
United States
Sandy
The price is AED 569
AED 632 total
includes taxes & fees
19 Jul - 20 Jul
Hilton Garden Inn Kent Island Marina

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,000 reviews)
"Beautiful view!!! Clean hotel and very nice helpful staff. Would stay again."
United States
Michele
The price is AED 511
AED 567 total
includes taxes & fees
30 Jun - 1 Jul
Holiday Inn Express Annapolis East-Kent Island by IHG

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,002 reviews)
"Good hotel for the price"
United States
Brenda
The price is AED 460
AED 510 total
includes taxes & fees
6 Jul - 7 Jul
Best Western Kent Narrows Inn

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (777 reviews)
"Great Stay!!"
United States
Richard
The price is AED 664
AED 738 total
includes taxes & fees
20 Jul - 21 Jul
Hyatt Place Kent Narrows & Marina

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (388 reviews)
"Breakfast is excellent, staff very friendly"
United States
Polina
The price is AED 551
AED 606 total
includes taxes & fees
28 Jun - 29 Jun
Knapps Narrows Marina & Inn

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
9.0 out of 10, Wonderful, (97 reviews)
"Super lovely, very cute even when our weather was pretty rainy."
United States
Jennifer
The price is AED 1,249
AED 1,557 total
includes taxes & fees
28 Jun - 29 Jun
Wylder Tilghman Island

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.4 out of 10, Exceptional, (137 reviews)
"The inn is very lovely. The views are spectacular. Very easy access to restaurants and shopping. "
United States
Tracey
The price is AED 826
AED 909 total
includes taxes & fees
29 Jun - 30 Jun
The Tilghman Island Inn

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (147 reviews)
"It was such a lovely quaint resort. I loved everything about staying there. Thank you."
United States
Sue
The price is AED 565
AED 752 total
includes taxes & fees
30 Jun - 1 Jul
Kent Island Resort

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, (467 reviews)
"Wonderful stay! Everything was amazing..,the staff, rooms, Knoxie’s Table, the spa! Couldn’t have asked for a better stay. I’ll definitely return."
United States
Damika
The price is AED 829
AED 1,013 total
includes taxes & fees
29 Jun - 30 Jun
The Inn at Chesapeake Bay Beach Club

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,002 reviews)
"Awesome spot and room, nice walking distance from multiple places"
United States
Travis
The price is AED 478
AED 641 total
includes taxes & fees
7 Jul - 8 Jul
Rod 'N' Reel Resort

Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (508 reviews)
"The room was very nice, clean and quiet. Great location"
United States
William
The price is AED 305
AED 348 total
includes taxes & fees
7 Jul - 8 Jul
Village Inn Annapolis MD

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (939 reviews)
"Definitely the view of the harbor from our room and how all the stores and restaurants were in walking distance"
United States
Salvatore
The price is AED 915
AED 1,043 total
includes taxes & fees
5 Jul - 6 Jul
Annapolis Waterfront Hotel, Autograph Collection

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 reviews)
"Great location. Beautiful room and exemplary service. "
United States
Nathan
The price is AED 835
AED 951 total
includes taxes & fees
28 Jun - 29 Jun
Flag House Inn

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
2.5 star property
Annapolis
9.8 out of 10, Exceptional, (38 reviews)
"Great property and super friendly staff!!"
United States
Chris
The price is AED 684
AED 780 total
includes taxes & fees
28 Jun - 29 Jun
134 Prince - Luxury Boutique Hotel
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.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Shady Side attractions

Learn more about Shady Side

Love dining out, parks, and museums? Get away to Shady Side!

A river with boats, a marina, and a town with houses and buildings.

Top Shady Side Hotel Reviews

More cheap stays in Shady Side

Find out more about Shady Side

Top reasons to visit Shady Side

  • Outdoor Activities: Shady Side is perfect for nature lovers, offering scenic marinas and urban parks for various recreational activities.
  • Family-Friendly Attractions: The area caters to families with fun experiences and educational opportunities for all ages.
  • Proximity to Annapolis: Just a short drive away, visitors can explore the vibrant downtown of Annapolis for dining and shopping.
  • Charming Accommodations: Enjoy a range of lodging options, from cozy bed & breakfasts to comfortable hotels.
  • Welcoming Atmosphere: Experience the friendly vibes of the locals while enjoying Shady Side's peaceful charm.

Find great hotels near Shady Side

Shady Side, Maryland, offers a delightful selection of accommodations, from charming bed & breakfasts to comfortable hotels. Whether you're seeking a pet-friendly stay, a business-friendly environment, or an LGBTQIA welcoming atmosphere, you'll find a range of options tailored to your needs. Explore the best hotels in the area and enjoy a memorable vacation experience with easy access to nearby attractions and scenic views.

  • Country Inn & Suites by Radisson, Annapolis, MD: Experience a warm and inviting atmosphere at Country Inn & Suites by Radisson, Annapolis. This 3-star hotel, located 16.1km from Shady Side, is perfect for travelers seeking a pet-friendly, LGBTQIA-welcoming space. Guests can enjoy the comforts of home with amenities tailored for business and leisure travelers alike. The hotel features a dog exercise area and a flexible pet policy, ensuring that your furry friends feel at home. With an emphasis on inclusivity and comfort, this hotel makes every visitor feel welcome.
  • Comfort Inn Conference Center: Ideal for families and business travelers alike, the Comfort Inn Conference Center is situated 20.9km from Shady Side. This hotel provides a friendly environment where children can thrive, featuring amenities such as a secure pool area. Pet-friendly accommodations ensure that your pets are welcome too, with a waived fee for service animals. With comfortable rooms and convenient access to local attractions, this property strikes a balance between family fun and business efficiency, making it a versatile choice for your stay.
  • Historic Inns of Annapolis: Step back in time at the Historic Inns of Annapolis, a 3.5-star hotel located 16.1km from Shady Side. Nestled in a national historic building, this hotel offers a unique blend of adventure and rich history. Guests can partake in nearby activities such as hiking, sailing, and kayaking, making it perfect for those seeking outdoor excitement. With a distinguished ambiance and a commitment to providing memorable experiences, this hotel is ideal for history buffs and adventure seekers alike.

Where to stay near Shady Side

Shady Side, Maryland, is the perfect destination for those seeking a family-friendly getaway amidst stunning scenery. Enjoy the peaceful atmosphere while exploring nearby attractions like vibrant downtown Annapolis, just a few miles away. Experience the charm of this quiet location, ideal for outdoor adventures and relaxing escapes, all while soaking in the welcoming vibes of friendly locals and beautiful surroundings. Shady Side promises a memorable experience for every traveler.

  • Annapolis: Located 16.1km from Shady Side, Annapolis is a vibrant city known for its rich history and stunning waterfront. Visitors flock to this charming destination year-round, with peak travel months from June to August. Annapolis offers a delightful mix of family-friendly activities, business opportunities, and urban exploration. Key highlights include the U.S. Naval Academy, picturesque beaches, and an array of shopping centers that cater to all tastes. Whether you're strolling through the historic district or enjoying the lively tourist precinct, Annapolis promises a memorable experience.
  • Galesville: Just 3.2km from Shady Side, Galesville is a quaint town that offers a perfect blend of outdoor adventure and scenic beauty. With moderate seasonality in visitor arrivals, the peak season from June to August invites travelers seeking a romantic getaway or outdoor fun. Galesville boasts charming recreational areas, educational sites, and shopping centers. Nature enthusiasts will love the nearby lake, beautiful beaches, and serene urban parks, making it an ideal spot for relaxation and exploration.
  • Churchton: Located 4.8km from Shady Side, Churchton is a picturesque city that draws visitors for its stunning outdoor landscapes and romantic ambiance. Travel peaks during the months of February, June to July, and October, offering a seasonal escape for nature lovers. With access to recreational areas, a scenic boardwalk, and educational facilities, Churchton is perfect for those who appreciate the great outdoors. Attractions such as the nearby lake, inviting beaches, and the expansive national state park provide ample opportunities for adventure and relaxation.

Things to do near Shady Side

Shady Side, Maryland, is perfect for outdoor family vacations, offering a variety of scenic activities. Visitors can enjoy the recreational areas, explore educational opportunities, and shop at local centers. It's an ideal destination for those looking to relax and connect with nature while engaging in fun activities with loved ones.

Shopping

If you're up for a drive, visit the Westfield Annapolis Mall, 16.1km away, for a variety of shops and entertainment. Closer to Shady Side, explore the Wild Bird Center, 12.9km away, or the Annapolis Harbor Center Shopping Center, 14.5km away, both offering family-friendly vibes.

Recreation

Navy-Marine Corps Memorial Stadium offers an energetic atmosphere for sports enthusiasts, just 16.1km from Shady Side. South River Golf Links, located 9.7km away, provides a scenic outdoor golf experience. For a touch of luxury, visit the Old South Country Club, situated 12.9km from town.

Adventure

Experience the thrill at Chesapeake Beach Water Park, where you can enjoy thrilling slides and family-friendly attractions, located 16.1km from Shady Side. For water sports enthusiasts, Annapolis Sailing School offers exciting sailing lessons 14.5km away. Explore the scenic St Michaels Nature Trail, 25.7km away, for a refreshing outdoor adventure.

Nightlife

Experience a vibrant nightlife in Shady Side with a visit to The Colonial Players for captivating theater performances. For family fun, check out Annapolis Bowl or Crofton Bowl, both offering exciting arcade adventures and a lively atmosphere perfect for all ages.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Shady Side

To save money on your trip to Shady Side, consider visiting from December to February when prices drop, especially on Mondays, the least expensive day to stay. Use Expedia’s search tool to filter your hotel options by budget and book a package that combines hotel, flights, and activities for additional savings. Look for flexible booking options and take advantage of good deals for great rates. For transportation, explore local public transport options, or enjoy the area on foot to keep costs down while discovering the scenic beauty of Shady Side.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Shady Side are December to February, where the prices are slightly lower. This is in comparison to May to July, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Shady Side is Monday. The most expensive day to stay in Shady Side is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to refine your choices based on your budget, desired location, and preferred hotel type. To find the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Shady Side hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in and around Shady Side

Shady Side, Maryland, offers a delightful blend of outdoor activities and family-friendly attractions. Visitors can explore scenic marinas, historic houses, and urban parks, making it an ideal destination for those seeking cultural experiences and natural beauty. Whether you’re interested in boating, history, or simply enjoying the great outdoors, Shady Side has something for everyone to enjoy during their vacation.

  • U.S. Naval Academy: Located 16.1km from Shady Side, the U.S. Naval Academy offers a unique glimpse into American naval history. Stroll through its picturesque campus, marvel at the stunning architecture, and enjoy scenic views along the waterfront.
  • Shadyside Park: Situated right in Shady Side, this urban park is perfect for families and outdoor enthusiasts. With playgrounds, picnic areas, and walking trails, it provides a refreshing escape in a vibrant city setting.
  • Galesville Heritage Museum: Just 3.2km away, this charming history museum showcases the rich culture of Galesville. Explore exhibits that highlight local heritage and learn about the area's fascinating past.

Best time to go to Shady Side

The best time to visit Shady Side can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Shady Side falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Shady Side falls in January, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.8°F (2.1°C)Light RainMostly SunnyAverageSlightly Low
February38.1°F (3.4°C)Light RainMostly SunnyAverageSlightly Low
March45.0°F (7.2°C)Light RainMostly SunnyAverageAverage
April55.0°F (12.8°C)Light RainMostly SunnyAverageAverage
May64.2°F (17.9°C)Light RainMostly SunnySlightly HighSlightly High
June73.0°F (22.8°C)Light RainMostly SunnySlightly HighSlightly High
July78.3°F (25.7°C)Light RainMostly SunnySlightly HighSlightly High
August76.6°F (24.8°C)Light RainMostly SunnyAverageAverage
September70.7°F (21.5°C)Light RainMostly SunnyAverageAverage
October60.4°F (15.8°C)Light RainMostly SunnySlightly LowAverage
November48.7°F (9.3°C)Light RainMostly SunnySlightly LowAverage
December41.5°F (5.3°C)Light RainMostly SunnySlightly LowSlightly Low

The nearest major airports for your trip to Shady Side

To reach Shady Side, Maryland, you can fly into three major airports. Washington, DC (DCA-Ronald Reagan Washington National) is situated 45.1km away, with luxury hotels like Salamander Washington DC and Riggs Washington DC, both within 4.8km, offering convenient access. Washington, DC (IAD-Washington Dulles Intl.) is 82.1km from Shady Side, featuring hotels such as the 4-star Hyatt Regency Dulles and Hilton Washington Dulles Airport, both within 3.2km. Lastly, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is only 40.2km away, with the 5-star Sagamore Pendry Baltimore and Four Seasons Hotel Baltimore located 12.9km from the airport, providing various transportation options.

Frequently asked questions

Where is the best place for a stay in Shady Side?
DoubleTree by Hilton Hotel Annapolis, located 9.8 mi (15.8 km) from the heart of Shady Side, is a top choice for your stay based on our traveler data. Two other choices for your trip to the area are Historic Inns of Annapolis and DoubleTree by Hilton Hotel Largo/Washington DC. See all available top hotels, or vacation rentals in Shady Side.
What are some of the best vacation rentals that Shady Side has to offer?
Charming Annapolis WaterVIEW Home: Visitors like this Shady Side vacation home rental. It is located on the waterfront and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. See all vacation rentals in Shady Side.
If I need to cancel my hotel reservation in Shady Side, will I receive a refund?
Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you booked a non-refundable reservation, you might be able to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Shady Side.
Where can I learn more about changing or cancelling my trip to Shady Side?
To find more details about updating your trip to Shady Side or cancelling it, click here.
Where is the best hotel to stay near Shadyside Park?
Anchored Inn at Hidden Harbour Marina is one of the top choices for your stay based on our traveler data, and this hotel offers an outdoor pool and free parking. It's located 4.8 mi (7.7 km) from Shadyside Park.
What about the best place to stay near Captain Avery Museum?
One of the top choices for your stay is Anchored Inn at Hidden Harbour Marina, located 5 mi (8.1 km) from Captain Avery Museum, and this hotel offers an outdoor pool and free parking.
What are some accommodations with pools in Shady Side?
DoubleTree by Hilton Hotel Largo/Washington DC: Hotel located near Northwest Stadium. Provides free self parking, an indoor pool, and a 24-hour fitness center. Comfort Inn Largo-Washington DC East and Crowne Plaza Annapolis by IHG are two additional hotels that offer an onsite pool. View all hotels with pools in Shady Side.
What's the best place to stay near Ronald Reagan Washington National Airport (DCA)?
Hyatt Regency Crystal City is a popular 4-star hotel featuring a restaurant and an outdoor pool. It's located a short 0.6 mi (1 km) from Ronald Reagan Washington National Airport. Other options near the airport are Courtyard by Marriott Arlington Crystal City/Reagan National and Hilton Garden Inn Reagan National Airport.
What is staying in Shady Side like?
Visitors can enjoy all that Shady Side has to offer including the shopping, restaurants, and parks. Tourists can also enjoy so much more including its museums. In Shady Side, there are 15 hotels and other accommodations to choose from. Find out more about Shady Side.
What should I see while I'm in Shady Side?
Natural beauty is on display at Shadyside Park, Northern Chesapeake Bay, and Chesapeake Bay. A couple of additional sights to add to your agenda are Captain Avery Museum and Franklin Point State Park. Check out what more to see and do in Expedia's Shady Side guide.
What's the weather like in Shady Side?
The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Shady Side is 51 inches.