Find hotels in Shady Side, MD from Rp1.289.384

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Go beyond your typical stay in Shady Side

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10 Nov - 11 Nov
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11 Nov - 12 Nov
This weekend
13 Nov - 15 Nov
Next weekend
20 Nov - 22 Nov

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Our top choices for Shady Side hotels

A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

1. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,274 reviews)
"Excellent staff & service!"
United States
Michele
The price is Rp1.616.795
Rp1.843.146 total
includes taxes & fees
22 Nov - 23 Nov
DoubleTree by Hilton Hotel Annapolis
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

2. The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,005 reviews)
"Excellent location, Very nice Hotel"
United States
Loraine
The price is Rp3.056.365
Rp3.484.256 total
includes taxes & fees
15 Nov - 16 Nov
The Westin Annapolis
A modern kitchen with a large island, bar stools, and a wine rack.

3. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (522 reviews)
"Everything was great"
United States
sherman
The price is Rp2.915.122
Rp3.323.239 total
includes taxes & fees
30 Nov - 1 Dec
Anchored Inn at Hidden Harbour Marina
A swimming pool with a clear blue water, surrounded by lounge chairs and a glass wall.

4. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,014 reviews)
"Great location"
United States
Jose
The price is Rp1.899.345
Rp2.165.254 total
includes taxes & fees
8 Dec - 9 Dec
Crowne Plaza Annapolis by IHG
The entrance to Rod N' Reel Resort with a covered walkway, a decorative fountain, and a stone wall with plants.

5. Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.8 out of 10, Excellent, (1,008 reviews)
"Place is gorgeous, clean and very welcoming."
United States
Patricia
The price is Rp2.622.724
Rp3.513.588 total
includes taxes & fees
30 Nov - 1 Dec
Rod 'N' Reel Resort
A historic brick building with a corner turret and multiple windows, located on a city street with flags and street lamps.

6. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (2,069 reviews)
"Great location, excellent stay"
United States
Christiaan
The price is Rp1.289.384
Rp2.088.542 total
includes taxes & fees
17 Nov - 18 Nov
Historic Inns of Annapolis
A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.

7. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,000 reviews)
"The hotel is close to lots of shopping and dining options."
United States
FRANK
The price is Rp2.152.115
Rp2.453.411 total
includes taxes & fees
29 Nov - 30 Nov
SpringHill Suites by Marriott Annapolis
A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.

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

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,064 reviews)
"Quiet and very convenient hotel. Staff was great, hotel was clean, good breakfast. Will definitely stay here whenever I’m back in Annapolis."
United States
Joel
The price is Rp1.649.717
Rp1.880.677 total
includes taxes & fees
30 Nov - 1 Dec
Country Inn & Suites by Radisson, Annapolis, MD
A hotel with a covered entrance, large columns, and a brick facade.

9. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
Annapolis
8.4 out of 10, Very good, (1,004 reviews)
"Great breakfast and hot tub"
United States
Marc
The price is Rp1.718.455
Rp1.959.039 total
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express & Suites Annapolis by IHG
A modern lounge area with a blue sofa, red chairs, and plaid armchairs. A coffee table with books and a vase of flowers is in the center. Large windows offer a view of a brick building with awnings.

10. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.2 out of 10, Wonderful, (1,013 reviews)
"Brunch was the best we had the whole trip! Excellent food and wonderful staff."
United States
REBECCA
The price is Rp2.358.444
Rp2.688.626 total
includes taxes & fees
29 Nov - 30 Nov
Graduate by Hilton Annapolis
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

11. 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, (514 reviews)
"Great property super friendly, helpful staff."
United States
scott
The price is Rp3.273.896
Rp4.094.107 total
includes taxes & fees
9 Dec - 10 Dec
The Inn at Chesapeake Bay Beach Club
A hot tub in a grassy area with a building in the background.

12. The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (20 reviews)
"The owners are very friendly and accommodating. Relaxing getaway"
United States
kristine
The price is Rp6.326.676
Rp7.212.479 total
includes taxes & fees
30 Nov - 1 Dec
The Inn at Tacaro Estate
A balcony with a table set for two, overlooking a marina with boats.

13. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (1,000 reviews)
"Staff was Great, Great Location. Nice Restaurant Bartender was great!"
United States
Donna
The price is Rp3.891.892
Rp4.436.756 total
includes taxes & fees
24 Nov - 25 Nov
Annapolis Waterfront Hotel, Autograph Collection
A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

14. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (1,010 reviews)
"Very quiet great location."
United States
Panagiotis
The price is Rp1.465.209
Rp1.670.338 total
includes taxes & fees
29 Nov - 30 Nov
Sonesta ES Suites Annapolis
An outdoor patio area with seating arrangements and a fire feature.

15. Courtyard by Marriott Bowie

Courtyard by Marriott Bowie
3.0 star property
Bowie
9.4 out of 10, Exceptional, (953 reviews)
"Great staff and hospitality, we will definitely be back again! Best experience we’ve had!"
United States
Halima
The price is Rp2.425.735
Rp2.741.081 total
includes taxes & fees
23 Nov - 24 Nov
Courtyard by Marriott Bowie
A modern lounge area with a sofa, chairs, a coffee table, and a bookshelf.

16. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,009 reviews)
"Great location, friendly staff."
United States
Joel
The price is Rp1.765.125
Rp2.012.243 total
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Annapolis Downtown
A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

17. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,004 reviews)
"We good stay"
United States
Mike
The price is Rp1.814.287
Rp2.068.288 total
includes taxes & fees
29 Nov - 30 Nov
Courtyard by Marriott Annapolis
A hotel lobby with a reception desk, seating area, and artwork on the walls.

18. Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,013 reviews)
"It was close to restaurants and the hotel was very clean and well maintained."
United States
Allison
The price is Rp1.772.330
Rp2.002.733 total
includes taxes & fees
7 Dec - 8 Dec
Comfort Inn Conference Center
A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.

19. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.2 out of 10, Very good, (1,008 reviews)
"Great location, many shops, restaurants, the breakfast at this location is the best we experienced in many Hampton Inns. The lady that takes care of breakfast there is the best"
United States
Christopher
The price is Rp1.586.778
Rp1.808.927 total
includes taxes & fees
17 Nov - 18 Nov
Hampton Inn & Suites Annapolis
A modern lobby with a reception desk, seating area, and potted plants.

20. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1,003 reviews)
"The room was clean, the staff were wonderful, we didn't do breakfast and we were charged $8.00 a day for parking."
United States
Walter
The price is Rp1.577.012
Rp1.797.794 total
includes taxes & fees
16 Nov - 17 Nov
Hilton Garden Inn Annapolis
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.
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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 savour its top-notch restaurants.
See properties

Learn more about Shady Side

Love dining, 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

A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis

10/10 Excellent

Really comfortable rooms. Quiet and large rooms. The swimming pool and hot tub were great. Gym facilities looked good but weren’t used. Breakfast not too bad
United Kingdom
Charlotte
Reviewed April 20, 2025
SpringHill Suites by Marriott Annapolis

Frequently Asked Questions

If I need to cancel my hotel reservation in Shady Side, will I receive a refund?

Yes, the majority of hotel room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Shady Side.

What are some accommodation options 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 on-site pool. View all hotels with pools in Shady Side.

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 accommodation options 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 itinerary are Captain Avery Museum and Franklin Point State Park. Take a look at what more there is 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 temperature of 24°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for Shady Side is 1307 mm.

What's the best place to 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 traveller data. Two other choices for your visit 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.