Find hotels in Shady Side, MD from Rp1.300.076

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Go beyond your typical stay in Shady Side

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Check prices for these dates

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14 Nov - 15 Nov
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15 Nov - 16 Nov
Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 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, (1,278 reviews)
"i enjoyed how close the place was to many local shops and resturants."
United States
michel demanche
The price is Rp1.627.252
Rp1.855.068 total
includes taxes & fees
29 Nov - 30 Nov
DoubleTree by Hilton Hotel Annapolis
A swimming pool with a clear blue water, surrounded by lounge chairs and a glass wall.

2. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,002 reviews)
"Great location"
United States
Jose
The price is Rp1.875.218
Rp2.137.748 total
includes taxes & fees
13 Dec - 14 Dec
Crowne Plaza Annapolis by IHG
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, (524 reviews)
"Great place, very clean and fresh. Right next to a cool boathouse boat bar and overlooking the marina."
United States
David
The price is Rp2.934.626
Rp3.345.474 total
includes taxes & fees
30 Nov - 1 Dec
Anchored Inn at Hidden Harbour Marina
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.

4. Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.8 out of 10, Excellent, (1,005 reviews)
"Place is gorgeous, clean and very welcoming."
United States
Patricia
The price is Rp2.639.688
Rp3.536.314 total
includes taxes & fees
10 Dec - 11 Dec
Rod 'N' Reel Resort
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

5. The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,000 reviews)
"Excellent location, Very nice Hotel"
United States
Loraine
The price is Rp2.894.754
Rp3.300.019 total
includes taxes & fees
29 Nov - 30 Nov
The Westin Annapolis
A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

6. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (2,066 reviews)
"Great location, excellent stay"
United States
Christiaan
The price is Rp1.300.076
Rp2.105.861 total
includes taxes & fees
23 Nov - 24 Nov
Historic Inns of Annapolis
A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.

7. 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, (1,060 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 Rp1.587.563
Rp1.809.822 total
includes taxes & fees
6 Dec - 7 Dec
Country Inn & Suites by Radisson, Annapolis, MD
A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.

8. 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 Rp2.166.514
Rp2.469.826 total
includes taxes & fees
29 Nov - 30 Nov
SpringHill Suites by Marriott Annapolis
A modern hotel room with a large bed, a separate bathroom with a bathtub, a desk, and a microwave.

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, (1,000 reviews)
"Great breakfast and hot tub"
United States
Marc
The price is Rp1.732.705
Rp1.975.284 total
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express & Suites Annapolis by IHG
A spacious atrium with a high ceiling, skylights, and a patterned floor.

10. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,000 reviews)
"Brunch was the best we had the whole trip! Excellent food and wonderful staff."
United States
REBECCA
The price is Rp2.378.001
Rp2.710.921 total
includes taxes & fees
29 Nov - 30 Nov
Graduate by Hilton Annapolis
A bar area with multiple seating options, including bar stools and tables, and a variety of bottles and glasses on shelves.

11. Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,015 reviews)
"It was close to restaurants and the hotel was very clean and well maintained."
United States
Allison
The price is Rp1.586.793
Rp1.793.076 total
includes taxes & fees
30 Nov - 1 Dec
Comfort Inn Conference Center
A modern lounge area with a sofa, chairs, a coffee table, and a bookshelf.

12. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,000 reviews)
"Great location, friendly staff."
United States
Joel
The price is Rp1.779.762
Rp2.028.928 total
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Annapolis Downtown
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 Rp3.917.931
Rp4.466.441 total
includes taxes & fees
7 Dec - 8 Dec
Annapolis Waterfront Hotel, Autograph Collection
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

14. 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 Rp3.295.800
Rp4.121.499 total
includes taxes & fees
9 Dec - 10 Dec
The Inn at Chesapeake Bay Beach Club
A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

15. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (1,005 reviews)
"Great stay"
United States
Salina
The price is Rp1.477.359
Rp1.684.190 total
includes taxes & fees
24 Nov - 25 Nov
Sonesta ES Suites Annapolis
An outdoor patio area with seating arrangements and a fire feature.

16. Courtyard by Marriott Bowie

Courtyard by Marriott Bowie
3.0 star property
Bowie
9.4 out of 10, Exceptional, (955 reviews)
"Great staff and hospitality, we will definitely be back again! Best experience we’ve had!"
United States
Halima
The price is Rp2.441.425
Rp2.758.809 total
includes taxes & fees
6 Dec - 7 Dec
Courtyard by Marriott Bowie
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, (1,001 reviews)
"It was very nice"
United States
Christopher
The price is Rp1.826.426
Rp2.082.126 total
includes taxes & fees
6 Dec - 7 Dec
Courtyard by Marriott Annapolis
A modern lobby with a reception desk, seating area, and potted plants.

18. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1,001 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 Rp1.514.739
Rp1.726.803 total
includes taxes & fees
23 Nov - 24 Nov
Hilton Garden Inn Annapolis
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

19. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (861 reviews)
"Great place to stay"
United States
Michael
The price is Rp2.441.425
Rp2.709.981 total
includes taxes & fees
25 Nov - 26 Nov
Hyatt Place Kent Narrows & Marina
A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.

20. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.2 out of 10, Very good, (1,000 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 Rp1.627.252
Rp1.855.068 total
includes taxes & fees
22 Nov - 23 Nov
Hampton Inn & Suites 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 spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.
Historic Inns of Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District

10/10 Excellent

Great for shopping. Close to Marina too.
United Kingdom
paul
Reviewed August 3, 2026
Historic Inns of 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.