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Check prices for these dates

Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec
In one month
26 Dec - 28 Dec
In two months
23 Jan - 25 Jan

Featured Villas in Shady Side

No exact matches found, but these alternatives could be just right

Recommended hotels in Shady Side

Exterior
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Holiday Home in Shady Side

10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
The price is NZ$747
includes taxes & fees
2 Dec - 3 Dec
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Exterior
Sunset Cottage - West River Access and Views!

Holiday Home in Shady Side

2.0 star property
The price is NZ$829
includes taxes & fees
8 Dec - 9 Dec
Sunset Cottage - West River Access and Views!
Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1039)
"Room was comfortable and the staff were courtesy!"
United States
Danny
The price is NZ$116
includes taxes & fees
21 Dec - 22 Dec
DoubleTree by Hilton Hotel Annapolis
Exterior
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3.0 star property
8.6 out of 10, Excellent, (1012)
"Clean room, great staff, great breakfast "
United States
Susanne
The price is NZ$145
includes taxes & fees
7 Dec - 8 Dec
Hilton Garden Inn Annapolis Downtown
Balcony
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4.0 star property
8.4 out of 10, Very good, (1002)
"Clean room, friendly & helpful staff"
United States
Anne
The price is NZ$237
includes taxes & fees
2 Dec - 3 Dec
Rod 'N' Reel Resort
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (928)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is NZ$153
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Balcony view
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (358)
"Yes. room was spotless and staff was awesome!"
United States
Frank
The price is NZ$230
includes taxes & fees
2 Dec - 3 Dec
Knapps Narrows Marina & Inn
Exterior
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

3.0 star property
8.2 out of 10, Very good, (1001)
"I had a lovely stay."
United States
Kalynn
The price is NZ$129
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Annapolis
View from property
St Michaels Inn

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1006)
"clean and comfy, friendly staff"
United States
Tamara
The price is NZ$211
includes taxes & fees
2 Dec - 3 Dec
St Michaels Inn
Exterior
Quality Inn

Quality Inn

2.5 star property
7.8 out of 10, Good, (857)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is NZ$165
includes taxes & fees
14 Dec - 15 Dec
Quality Inn
Exterior
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1010)
"Nice big rooms, comfortable beds. Well maintained. "
United States
Margaret
The price is NZ$243
includes taxes & fees
21 Dec - 22 Dec
Graduate by Hilton Annapolis
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
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 NZ$269
includes taxes & fees
7 Dec - 8 Dec
Kent Island Resort
Exterior
Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (160)
"Beautiful and very modern, breakfast was great"
United States
Dominic
The price is NZ$235
includes taxes & fees
7 Dec - 8 Dec
Fairfield Inn & Suites By Marriott Annapolis
Exterior
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1015)
"Wonderful country inn!"
United States
Jennifer
The price is NZ$165
includes taxes & fees
21 Dec - 22 Dec
Country Inn & Suites by Radisson, Annapolis, MD
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

2.0 star property
8.8 out of 10, Excellent, (89)
"Very relaxing stay."
United States
Anne
The price is NZ$307
includes taxes & fees
1 Jan - 2 Jan 2026
Wylder Tilghman Island
Exterior
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very good, (1004)
"Staff at front desk were incredibly friendly and helpful!"
United States
Nina
The price is NZ$149
includes taxes & fees
19 Dec - 20 Dec
Holiday Inn Express & Suites Annapolis by IHG
Exterior
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1910)
"Front desk staff was very helpful, and the location was perfect for exploring downtown Annapolis!"
United States
Christine
Historic Inns of Annapolis
Exterior
Best Western Annapolis

Best Western Annapolis

2.5 star property
7.8 out of 10, Good, (1012)
"Clean room, nice staff and plenty of parking "
United States
Chauntese
The price is NZ$131
includes taxes & fees
7 Dec - 8 Dec
Best Western Annapolis
Exterior
Comfort Inn Conference Center

Comfort Inn Conference Center

2.5 star property
9.2 out of 10, Wonderful, (1014)
"It had good parking and restaurant in the hotel with good prices."
United States
Patrick
The price is NZ$195
includes taxes & fees
15 Dec - 16 Dec
Comfort Inn Conference Center
Marina
Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

2.5 star property
9.4 out of 10, Exceptional, (470)
"Overnight stay - all went as expected"
United States
William
The price is NZ$267
includes taxes & fees
29 Dec - 30 Dec
Anchored Inn at Hidden Harbour Marina
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Great location and customer care "
Robert 2-night trip
Posted 1 day ago
Graduate by Hilton Annapolis

Find out more about Shady Side

Shady Side Villas information

Number of reviews
14,976
Accommodation
3 Villas
Lowest Price
NZ$116
Highest Price
NZ$829

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