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

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Nov 6 - Nov 8
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Nov 13 - Nov 15

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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, (1,269 reviews)
"Excellent staff & service!"
United States
Michele
The price is ļæ„14,112
ļæ„16,088 total
includes taxes & fees
Nov 10 - Nov 11
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, (1,004 reviews)
"Great location"
United States
Jose
The price is ļæ„15,947
ļæ„18,180 total
includes taxes & fees
Nov 10 - Nov 11
Crowne Plaza Annapolis by IHG
A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.

3. 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 ļæ„19,578
ļæ„22,319 total
includes taxes & fees
Nov 22 - Nov 23
SpringHill Suites by Marriott Annapolis
A hotel with a covered entrance, large columns, and a brick facade.

4. 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)
"Staff were friendly and helpful."
United States
Connie
The price is ļæ„13,894
ļæ„15,839 total
includes taxes & fees
Nov 23 - Nov 24
Holiday Inn Express & Suites Annapolis by IHG
A historic brick building with a corner turret and multiple windows, located on a city street with flags and street lamps.

5. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (2,067 reviews)
"Great location, excellent stay"
United States
Christiaan
The price is ļæ„13,528
ļæ„20,821 total
includes taxes & fees
Dec 1 - Dec 2
Historic Inns of Annapolis
A multi-story hotel with a central entrance, a landscaped garden with flowers, and a metal sculpture.

6. 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 ļæ„25,547
ļæ„29,124 total
includes taxes & fees
Nov 29 - Nov 30
Anchored Inn at Hidden Harbour Marina
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

7. The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,000 reviews)
"This is a fabulous resort! Very clean, great location and the staff is great!"
United States
Bobbi
The price is ļæ„26,683
ļæ„30,419 total
includes taxes & fees
Nov 22 - Nov 23
The Westin 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, (1,056 reviews)
"I have stayed here before. Very nice hotel cause it is in a great location."
United States
Michael
The price is ļæ„13,768
ļæ„15,696 total
includes taxes & fees
Nov 24 - Nov 25
Country Inn & Suites by Radisson, Annapolis, MD
The entrance to Rod N' Reel Resort with a covered walkway, a decorative fountain, and a stone wall with plants.

9. Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.8 out of 10, Excellent, (1,001 reviews)
"As far as I'm concerned one of the best places to stay in the area"
United States
Joseph
The price is ļæ„19,891
ļæ„27,337 total
includes taxes & fees
Nov 30 - Dec 1
Rod 'N' Reel Resort
A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.

10. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,006 reviews)
"Brunch was the best we had the whole trip! Excellent food and wonderful staff."
United States
REBECCA
The price is ļæ„20,586
ļæ„23,468 total
includes taxes & fees
Nov 29 - Nov 30
Graduate by Hilton Annapolis
A hotel lobby with a reception desk, seating area, and artwork on the walls.

11. Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,005 reviews)
"Clean room, great staff, good breakfast and enjoyable pool would stay here again."
United States
Gloria
The price is ļæ„17,210
ļæ„19,447 total
includes taxes & fees
Nov 15 - Nov 16
Comfort Inn Conference Center
Lobby

12. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,004 reviews)
"Great location, friendly staff."
United States
Joel
The price is ļæ„16,054
ļæ„18,302 total
includes taxes & fees
Dec 2 - Dec 3
Hilton Garden Inn Annapolis Downtown
A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

13. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,001 reviews)
"We good stay"
United States
Mike
The price is ļæ„15,358
ļæ„17,508 total
includes taxes & fees
Nov 29 - Nov 30
Courtyard by Marriott Annapolis
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, (1,006 reviews)
"Very quiet great location."
United States
Panagiotis
The price is ļæ„13,105
ļæ„14,939 total
includes taxes & fees
Nov 29 - Nov 30
Sonesta ES Suites Annapolis
A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.

15. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.2 out of 10, Very good, (1,004 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 ļæ„14,112
ļæ„16,088 total
includes taxes & fees
Nov 22 - Nov 23
Hampton Inn & Suites Annapolis
A modern lobby with a reception desk, seating area, and potted plants.

16. 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 ļæ„13,768
ļæ„15,696 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Garden Inn Annapolis
A balcony with a table set for two, overlooking a marina with boats.

17. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (1,002 reviews)
"Easy access to downtown, Great waterside restaurants."
United States
John
The price is ļæ„35,375
ļæ„40,328 total
includes taxes & fees
Nov 29 - Nov 30
Annapolis Waterfront Hotel, Autograph Collection
A modern hotel kitchen with a central island, seating area, and various kitchen appliances.

18. Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,005 reviews)
"Clean comfy bed"
United States
Dawnmarie
The price is ļæ„10,659
ļæ„12,152 total
includes taxes & fees
Nov 23 - Nov 24
Best Western Annapolis
An outdoor patio area with seating arrangements and a fire feature.

19. Courtyard by Marriott Bowie

Courtyard by Marriott Bowie
3.0 star property
Bowie
9.4 out of 10, Exceptional, (950 reviews)
"Great staff and hospitality, we will definitely be back again! Best experience weā€™ve had!"
United States
Halima
The price is ļæ„21,173
ļæ„23,925 total
includes taxes & fees
Nov 29 - Nov 30
Courtyard by Marriott Bowie
A circular fire pit surrounded by outdoor seating with a brick wall and a multi-story building in the background.

20. TownePlace Suites by Marriott Annapolis

TownePlace Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (143 reviews)
"It was AMAZING to stay there !!!"
United States
Nkusu Lauren
The price is ļæ„18,631
ļæ„21,240 total
includes taxes & fees
Nov 10 - Nov 11
TownePlace Suites by Marriott 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 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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"The fireplace and hot tub in the room"
Tyrisha 2-night trip
Posted 15 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

More cheap stays in Shady Side

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
The price is ļæ„10,659 per night from Nov 23 to Nov 24
ļæ„10,659
ļæ„12,152 total
Nov 23 - Nov 24
includes taxes & fees

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 75Ā°F, while the coldest months are January and February with an average of 40Ā°F. Average annual precipitation for Shady Side is 51 inches.

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