Villas in Shady Side

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Villas in Shady Side

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Recommended hotels in Shady Side

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

Vacation Home in Shady Side

10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
$376 nightly
The price is $429
Dec 2 - Dec 3
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Exterior
Sunset Cottage - West River Access and Views!

Vacation Home in Shady Side

2.0 star property
$470 nightly
The price is $477
Dec 8 - Dec 9
Total with taxes and fees
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, (1040)
"room was clean and quiet; parking was easy and safe. Very good welcome cookies too."
United States
Francisco
$61 nightly
The price is $70
Dec 21 - Dec 22
Total with taxes and fees
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, (1013)
"Clean room, great staff, great breakfast "
United States
Susanne
$79 nightly
The price is $90
Dec 28 - Dec 29
Total with taxes and fees
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, (1003)
"Clean room, friendly & helpful staff"
United States
Anne
$124 nightly
The price is $136
Dec 2 - Dec 3
Total with taxes and fees
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
$79 nightly
The price is $88
Dec 14 - Dec 15
Total with taxes and fees
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, (359)
"Yes. room was spotless and staff was awesome!"
United States
Frank
$120 nightly
The price is $132
Dec 2 - Dec 3
Total with taxes and fees
Knapps Narrows Marina & Inn
Exterior
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

3.0 star property
8.2 out of 10, Very Good, (1002)
"I had a lovely stay."
United States
Kalynn
$65 nightly
The price is $74
Dec 21 - Dec 22
Total with taxes and fees
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
$108 nightly
The price is $119
Dec 4 - Dec 5
Total with taxes and fees
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
$85 nightly
The price is $94
Dec 14 - Dec 15
Total with taxes and fees
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
$122 nightly
The price is $139
Dec 21 - Dec 22
Total with taxes and fees
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
$142 nightly
The price is $154
Dec 7 - Dec 8
Total with taxes and fees
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
$118 nightly
The price is $135
Dec 7 - Dec 8
Total with taxes and fees
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
$83 nightly
The price is $95
Dec 28 - Dec 29
Total with taxes and fees
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
$160 nightly
The price is $176
Jan 1 - Jan 2, 2026
Total with taxes and fees
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
$75 nightly
The price is $86
Dec 19 - Dec 20
Total with taxes and fees
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, (1911)
"Excellent hotel Really nice staff Love the valet guys "
United States
ben
$144 nightly
The price is $164
Jan 1 - Jan 2, 2026
Total with taxes and fees
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
$66 nightly
The price is $75
Dec 7 - Dec 8
Total with taxes and fees
Best Western Annapolis
Exterior
Comfort Inn Conference Center

Comfort Inn Conference Center

2.5 star property
9.2 out of 10, Wonderful, (1016)
"It had good parking and restaurant in the hotel with good prices."
United States
Patrick
$99 nightly
The price is $112
Dec 8 - Dec 9
Total with taxes and fees
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
$149 nightly
The price is $170
Dec 29 - Dec 30
Total with taxes and fees
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

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Evening bar staff was exceptional, as was the crew at the check-in desk. Excellent recommendations for places to eat. This hotel is within walking distance of everything we wanted to see and do. So much history here, cool stores, venues, and not far from the bay."
Jan Michael 2-night trip
Posted 2 days ago
Hilton Garden Inn Annapolis Downtown

Find out more about Shady Side

Shady Side Villas information

Number of reviews
14,974
Accommodation
3 Villas
Lowest Price
$70
Highest Price
$477

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