Find hotels in Shady Side, MD from ฿2,376

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29 Nov - 30 Nov
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30 Nov - 1 Dec
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5 Dec - 7 Dec
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Top 10 Shady Side hotels and places to stay

Exterior
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, (925)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is ฿2,552
฿2,833 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1005)
"Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay"
United States
Roberta
The price is ฿3,828
฿4,249 total
includes taxes & fees
11 Dec - 12 Dec
Hilton Garden Inn Kent Island Marina
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.4 out of 10, Exceptional, (667)
"My favorite hotel "
United States
Jen
The price is ฿3,728
฿4,138 total
includes taxes & fees
1 Dec - 2 Dec
Hyatt Place Kent Narrows & Marina
View from property
The Westin Annapolis

The Westin Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1004)
"Great environment"
United States
Salvador E
The price is ฿4,886
฿5,570 total
includes taxes & fees
17 Dec - 18 Dec
The Westin Annapolis
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 star property
Annapolis
8.8 out of 10, Excellent, (1012)
"Clean, easy parking, nice staff but over priced breakfast"
United States
Gabrielle
The price is ฿3,442
฿3,924 total
includes taxes & fees
2 Dec - 3 Dec
Crowne Plaza Annapolis by IHG
Balcony
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4.0 star property
Chesapeake Beach
8.4 out of 10, Very good, (1002)
"Clean room, friendly & helpful staff"
United States
Anne
The price is ฿3,349
฿4,360 total
includes taxes & fees
30 Nov - 1 Dec
Rod 'N' Reel Resort
Premium bedding, pillow-top beds, in-room safe, individually furnished
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

2.5 star property
Annapolis
8.2 out of 10, Very good, (1010)
"I had a great experience at my stay at Hampton "
United States
Idris O
The price is ฿2,810
฿3,203 total
includes taxes & fees
7 Dec - 8 Dec
Hampton Inn & Suites Annapolis
Exterior
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

3.0 star property
Annapolis
8.6 out of 10, Excellent, (1002)
"Wonderful stay. "
United States
Angela
The price is ฿3,111
฿3,547 total
includes taxes & fees
22 Dec - 23 Dec
Courtyard by Marriott Annapolis
Hypo-allergenic bedding, desk, blackout curtains, iron/ironing board
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, (1014)
"Wonderful country inn!"
United States
Jennifer
The price is ฿2,810
฿3,203 total
includes taxes & fees
28 Dec - 29 Dec
Country Inn & Suites by Radisson, Annapolis, MD
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (127)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is ฿3,574
฿5,073 total
includes taxes & fees
7 Dec - 8 Dec
Kent Island Resort
Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1030)
"Room was comfortable and the staff were courtesy!"
United States
Danny
The price is ฿2,101
฿2,395 total
includes taxes & fees
22 Dec - 23 Dec
DoubleTree by Hilton Hotel Annapolis
Outdoor banquet area
The Tilghman Island Inn

The Tilghman Island Inn

3.5 star property
Tilghman
9.6 out of 10, Exceptional, (119)
"Great room and water view! Staff is very friendly and welcoming. "
United States
Nicole
The price is ฿6,422
฿7,064 total
includes taxes & fees
30 Nov - 1 Dec
The Tilghman Island Inn
Hypo-allergenic bedding, in-room safe, desk, iron/ironing board
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

3.0 star property
Annapolis
8.2 out of 10, Very good, (1001)
"I had a lovely stay."
United States
Kalynn
The price is ฿2,084
฿2,376 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Annapolis
Room, 2 Queen Beds, Balcony | Premium bedding, down duvets, pillow-top beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
Historic District
8.8 out of 10, Excellent, (878)
"Clean room. Friendly staff awesome location. "
United States
Brent
The price is ฿4,698
฿5,355 total
includes taxes & fees
18 Dec - 19 Dec
Annapolis Waterfront Hotel, Autograph Collection
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 star property
Grasonville
8.0 out of 10, Very good, (1009)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
The price is ฿2,955
฿3,280 total
includes taxes & fees
8 Dec - 9 Dec
Best Western Kent Narrows Inn
Egyptian cotton sheets, premium bedding, pillow-top beds, desk
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3.0 star property
Edgewater
8.8 out of 10, Excellent, (956)
"Nice breakfast, clean room, great parking"
United States
Amy
The price is ฿2,674
฿3,049 total
includes taxes & fees
21 Dec - 22 Dec
Sonesta ES Suites Annapolis
Front of property – evening/night
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, (428)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
The price is ฿5,903
฿7,370 total
includes taxes & fees
2 Dec - 3 Dec
The Inn at Chesapeake Bay Beach Club
Terrace/patio
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 star property
Historic District
9.0 out of 10, Wonderful, (1907)
"Front desk staff was very helpful, and the location was perfect for exploring downtown Annapolis!"
United States
Christine
Historic Inns of Annapolis
Free daily buffet breakfast
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
Annapolis
8.2 out of 10, Very good, (1002)
"Staff at front desk were incredibly friendly and helpful!"
United States
Nina
The price is ฿2,423
฿2,762 total
includes taxes & fees
19 Dec - 20 Dec
Holiday Inn Express & Suites Annapolis by IHG
Suite, 1 Bedroom, Terrace | Living area | 42-inch LED TV with digital channels, TV
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3.0 star property
Annapolis
8.6 out of 10, Excellent, (1010)
"Clean room, great staff, great breakfast "
United States
Susanne
The price is ฿2,389
฿2,723 total
includes taxes & fees
7 Dec - 8 Dec
Hilton Garden Inn Annapolis Downtown
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

Captain Avery Museum

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

Top Shady Side Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"I have stayed several times over the last month or so totaling at leadt 7 nights and during every stay i have had a great experiene. Particularly with Chrissy who ive seen maonly during the night shift. Cannot understate how helpful and pleasant she has been. Probably the reason i wont stay anywhere else(if theres availability) in and around the Annapolis area. Keep up the amazing customer service!! 5 STARS "
Michael 2-night trip
Posted 5 days ago
Country Inn & Suites by Radisson, Annapolis, MD
Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"Nice"
Donavan 1-night trip
Posted 8 days ago
Comfort Inn Conference Center

More cheap stays in Shady Side

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills

2525 Evergreen Rd. Gambrills MD
The price is ฿2,543 per night from 8 Dec to 9 Dec
฿2,543
฿2,899 total
8 Dec - 9 Dec
includes taxes & fees
9/10 Wonderful! (1,008 reviews)

Frequently asked questions

What's the best place to stay in Shady Side?
DoubleTree by Hilton Hotel Largo/Washington DC, located 18.8 mi (30.3 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 Crowne Plaza Annapolis by IHG and DoubleTree by Hilton Hotel Annapolis. See all available top hotels, or 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 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?
DoubleTree by Hilton Hotel Largo/Washington DC: Hotel located near Northwest Stadium. Features free self parking, an indoor pool and a 24-hour fitness centre. Crowne Plaza Annapolis by IHG 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 13 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 Shadyside Park, Northern Chesapeake Bay and Chesapeake Bay. 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.

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