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

Find hotels in Shady Side, MD from AED 317

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Check prices for these dates

Tonight
14 Oct - 15 Oct
Tomorrow
15 Oct - 16 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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Our top choices for Shady Side hotels

1. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
Deale
United States
Beverly
AED 681
AED 777 total
includes taxes & fees
18 Oct - 19 Oct
Anchored Inn at Hidden Harbour Marina

2. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
United States
Lisa
AED 437
AED 498 total
includes taxes & fees
1 Nov - 2 Nov
SpringHill Suites by Marriott Annapolis

3. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
Annapolis
Canada
Omer
AED 349
AED 398 total
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express & Suites Annapolis by IHG

4. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
Michele
AED 389
AED 443 total
includes taxes & fees
18 Oct - 19 Oct
DoubleTree by Hilton Hotel Annapolis

5. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District
United States
Ashley
AED 315
AED 484 total
includes taxes & fees
21 Oct - 22 Oct
Historic Inns of Annapolis

6. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
Annapolis
United States
Jose
AED 404
AED 461 total
includes taxes & fees
25 Oct - 26 Oct
Crowne Plaza Annapolis by IHG

7. Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
Annapolis
United States
Catherine
AED 335
AED 382 total
includes taxes & fees
9 Nov - 10 Nov
Country Inn & Suites by Radisson, Annapolis, MD

8. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater
United States
Dennis
AED 342
AED 389 total
includes taxes & fees
21 Oct - 22 Oct
Sonesta ES Suites Annapolis

9. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
United States
Courtney
AED 358
AED 409 total
includes taxes & fees
20 Oct - 21 Oct
Hampton Inn & Suites Annapolis

10. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
United States
William
AED 820
AED 935 total
includes taxes & fees
2 Nov - 3 Nov
Annapolis Waterfront Hotel, Autograph Collection

11. Best Western Annapolis

Best Western Annapolis
Annapolis
United States
Silvia
AED 278
AED 317 total
includes taxes & fees
15 Nov - 16 Nov
Best Western Annapolis

12. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
Annapolis
United Kingdom
petra
AED 389
AED 443 total
includes taxes & fees
25 Oct - 26 Oct
Hilton Garden Inn Annapolis Downtown

13. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
Annapolis
United States
Jim
AED 368
AED 420 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Annapolis

14. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
Annapolis
United States
Glenn
AED 340
AED 388 total
includes taxes & fees
9 Nov - 10 Nov
Hilton Garden Inn Annapolis

15. Comfort Inn Conference Center

Comfort Inn Conference Center
Bowie
United States
Gloria
AED 400
AED 452 total
includes taxes & fees
25 Oct - 26 Oct
Comfort Inn Conference Center

16. TownePlace Suites by Marriott Annapolis

TownePlace Suites by Marriott Annapolis
Annapolis
United States
Nkusu Lauren
AED 419
AED 477 total
includes taxes & fees
20 Oct - 21 Oct
TownePlace Suites by Marriott Annapolis

17. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
Annapolis
United States
Imola
AED 496
AED 565 total
includes taxes & fees
27 Oct - 28 Oct
Fairfield Inn & Suites By Marriott Annapolis

18. The Westin Annapolis

The Westin Annapolis
Annapolis
United States
Bobbi
AED 731
AED 833 total
includes taxes & fees
25 Oct - 26 Oct
The Westin Annapolis

19. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
United States
Mark
AED 539
AED 615 total
includes taxes & fees
26 Oct - 27 Oct
Graduate by Hilton Annapolis

20. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
United States
BARBARA
AED 551
AED 606 total
includes taxes & fees
18 Oct - 19 Oct
Knapps Narrows Marina & Inn
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Stay near popular Shady Side attractions

Shadyside Park

Explore the great outdoors at Shadyside Park, a lovely green space in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.
See properties

Captain Avery Museum

You can spend time exploring the galleries in Captain Avery Museum in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.
See properties

Learn more about Shady Side

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

See all hotels in Shady Side
A river with boats, a marina, and a town with houses and buildings.

Top Shady Side Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Perfect place to stay! Classy. Clean comfortable amazing staff"
Nila 2-night trip
Posted 1 hour ago
Annapolis Waterfront Hotel, Autograph Collection
Microtel Inn & Suites by Wyndham Gambrills/Odenton

Microtel Inn & Suites by Wyndham Gambrills/Odenton

10/10 Excellent
"VERY AWESOME PLACE TO STAY"
Tucker 2-night trip
Posted 3 hours ago
Microtel Inn & Suites by Wyndham Gambrills/Odenton
Comfort Inn Conference Center

Comfort Inn Conference Center

8/10 Good
"Rate was fair. Room and property were good. I was not comfortable with the front desk making a photo copy of my driver license. There is no need for this and I have never had any hotel copy my license, they only check it to verify identity. This creates a huge risk for identity theft because there is no guarantee they dispose of the copy properly or store it securely."
William 1-night trip
Posted 3 hours ago
Comfort Inn Conference Center
Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"It was a great experience."
Jerry 1-night trip
Posted 4 hours ago
Historic Inns of Annapolis
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

10/10 Excellent
"I would like to say place I stayed at was nice, comfortable quiet, and have plenty of breakfast buffet"
Benjamin .E 1-night trip
Posted 5 hours ago
Comfort Inn Largo-Washington DC East
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

8/10 Good
"Room was awesome, very clean housekeeping staff extremely nice. Would suggest more help in the restaurant, food was excellent, poor waitress was running around trying to serve everyone!"
Andrea 3-night trip
Posted 1 day ago
Hilton Garden Inn Annapolis Downtown
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"We stayed at the Wilson’s Cove section next to the marina. Very nice accommodations. Restaurant was at the main hotel two blocks away. The staff was very friendly and the check-in staff at the main hotel helped me to get the room without having to pay extra since there was an Expedia reservation foul up."
Craig 1-night trip
Posted 2 days ago
The Inn at Chesapeake Bay Beach Club
St Michaels Inn

St Michaels Inn

10/10 Excellent
"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help in a variety of ways, local auto shop, contact with a driver, fresh coffee, etc."
Mary 1-night trip
Posted 2 days ago
St Michaels Inn
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Easy parking. Super comfy bed."
Kristen 1-night trip
Posted 5 days ago
The Westin Annapolis

More cheap stays in Shady Side

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
AED 278
AED 317 total
15 Nov - 16 Nov
includes taxes & fees
7.8/10 Good! (1,000 reviews)
Best Western Annapolis
St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
AED 294
AED 324 total
1 Nov - 2 Nov
includes taxes & fees
8/10 Very Good! (1,000 reviews)
St Michaels Inn
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD
AED 330
AED 366 total
8 Nov - 9 Nov
includes taxes & fees
Best Western Kent Narrows Inn
Microtel Inn & Suites by Wyndham Gambrills/Odenton

Microtel Inn & Suites by Wyndham Gambrills/Odenton

2525 Evergreen Rd. Gambrills MD
AED 328
AED 374 total
3 Nov - 4 Nov
includes taxes & fees
9.2/10 Wonderful! (1,159 reviews)
Microtel Inn & Suites by Wyndham Gambrills/Odenton
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD
AED 349
AED 398 total
15 Nov - 16 Nov
includes taxes & fees
Holiday Inn Express & Suites Annapolis by IHG
Comfort Inn Conference Center

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD
AED 400
AED 452 total
25 Oct - 26 Oct
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
Comfort Inn Conference Center

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 Crowne Plaza Annapolis by IHG. 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?
Lovely bay views with kayaks, bikes, fire pit, crabbing & more: This Shady Side vacation home rental offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 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 garden and a selection of games. 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?
Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access. Rod 'N' Reel Resort and Comfort Inn Largo-Washington DC East 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 Northern Chesapeake Bay, Chesapeake Bay, and Shadyside Park. 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.