Shady Side Hotels from ₹7,480

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7 Dec - 8 Dec
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8 Dec - 9 Dec
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12 Dec - 14 Dec
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19 Dec - 21 Dec

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Top 10 Shady Side hotels and places to stay

Front of property
The Oaks Waterfront

The Oaks Waterfront

4.0 star property
Easton
10.0 out of 10, Exceptional, (41)
"Loved the Oaks! Fabulous accommodations and excellent staff"
United States
Barbara
The price is ₹37,176
₹40,893 total
includes taxes & fees
8 Dec - 9 Dec
The Oaks Waterfront
Front of property
St Michaels Inn

St Michaels Inn

2.5 star property
St. Michaels
8.2 out of 10, Very good, (1002)
"clean and comfy, friendly staff"
United States
Tamara
The price is ₹9,455
₹10,400 total
includes taxes & fees
7 Jan - 8 Jan 2026
St Michaels Inn
Premium Room | Frette Italian sheets, premium bedding, iron/ironing board, free WiFi
The Wildset

The Wildset

2.5 star property
St. Michaels
9.8 out of 10, Exceptional, (407)
"Awesome! Love the room and fireplace!"
United States
Brian
The price is ₹17,909
₹21,679 total
includes taxes & fees
8 Dec - 9 Dec
The Wildset
Breakfast, lunch, dinner served; sea views
Inn at Perry Cabin

Inn at Perry Cabin

5.0 star property
St. Michaels
9.6 out of 10, Exceptional, (371)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is ₹42,278
₹51,157 total
includes taxes & fees
28 Dec - 29 Dec
Inn at Perry Cabin
Porch
Parsonage Inn

Parsonage Inn

3.5 star property
St. Michaels
9.2 out of 10, Wonderful, (130)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is ₹17,999
₹19,798 total
includes taxes & fees
1 Jan - 2 Jan 2026
Parsonage Inn
Exterior
George Brooks House B&B

George Brooks House B&B

3.0 star property
St. Michaels
8.6 out of 10, Excellent, (65)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
The price is ₹13,769
₹15,146 total
includes taxes & fees
1 Jan - 2 Jan 2026
George Brooks House B&B
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets
Quality Inn

Quality Inn

2.5 star property
Grasonville
7.8 out of 10, Good, (859)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is ₹7,649
₹8,491 total
includes taxes & fees
14 Dec - 15 Dec
Quality Inn
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, (1004)
"Room was great! In room tub was a bit smaller than I was expecting but still quite adequate! View from room was very nice."
United States
Madeline
The price is ₹9,287
₹10,309 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Kent Island Marina
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, (930)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is ₹7,109
₹7,891 total
includes taxes & fees
18 Dec - 19 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (1004)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
The price is ₹7,507
₹8,333 total
includes taxes & fees
22 Dec - 23 Dec
Best Western Kent Narrows Inn
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.6 out of 10, Exceptional, (673)
"Great view, good ambiance all around"
United States
Dianne
The price is ₹10,448
₹11,597 total
includes taxes & fees
14 Dec - 15 Dec
Hyatt Place Kent Narrows & Marina
Exterior
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3.0 star property
Tilghman
9.4 out of 10, Exceptional, (359)
"Courteous and helpful staff. Comfortable, clean rooms in a beautiful setting. We enjoy our stays and always feel so welcomed!"
United States
Virginia
The price is ₹10,799
₹11,879 total
includes taxes & fees
8 Dec - 9 Dec
Knapps Narrows Marina & Inn
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
The price is ₹12,149
₹17,324 total
includes taxes & fees
1 Jan - 2 Jan 2026
Wylder Tilghman Island
Outdoor banquet area
The Tilghman Island Inn

The Tilghman Island Inn

3.5 star property
Tilghman
9.6 out of 10, Exceptional, (120)
"Great room and water view! Staff is very friendly and welcoming. "
United States
Nicole
The price is ₹17,999
₹19,798 total
includes taxes & fees
8 Dec - 9 Dec
The Tilghman Island Inn
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"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 ₹11,514
₹15,941 total
includes taxes & fees
9 Dec - 10 Dec
Kent Island Resort
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, (429)
"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 ₹16,545
₹20,654 total
includes taxes & fees
10 Dec - 11 Dec
The Inn at Chesapeake Bay Beach Club
Balcony
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4.0 star property
Chesapeake Beach
8.4 out of 10, Very good, (1000)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is ₹9,569
₹12,422 total
includes taxes & fees
2 Jan - 3 Jan 2026
Rod 'N' Reel Resort
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, (880)
"Great location, nice and clean "
United States
Micah
The price is ₹15,987
₹18,225 total
includes taxes & fees
14 Dec - 15 Dec
Annapolis Waterfront Hotel, Autograph Collection
Front of property
Flag House Inn

Flag House Inn

3.5 star property
Historic District
9.4 out of 10, Exceptional, (83)
"The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. "
United States
Elizabeth
The price is ₹16,457
₹18,761 total
includes taxes & fees
8 Dec - 9 Dec
Flag House Inn
Exterior
134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel

2.5 star property
Annapolis
9.8 out of 10, Exceptional, (30)
"Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff"
United States
Ian
134 Prince - Luxury Boutique Hotel
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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Top Shady Side Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Very welcoming & clean & right in the middle of everything!"
JoAnne 1-night trip
Posted 6 hours ago
DoubleTree by Hilton Hotel Annapolis

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 ₹6,911 per night from 29 Dec to 30 Dec
₹6,911
₹7,879 total
29 Dec - 30 Dec
includes taxes & fees
9/10 Wonderful! (1,003 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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