Shady Side Chalets

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Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8
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

Vacation Home in Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
$374 nightly
The price is $426
Dec 14 - Dec 15
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

Sunset Cottage - West River Access and Views!
2.0 star property
$461 nightly
The price is $467
Dec 16 - Dec 17
Total with taxes and fees
Sunset Cottage - West River Access and Views!
Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
8.6 out of 10, Excellent, (1006)
"Great place!"
United States
Tawnya
$76 nightly
The price is $87
Dec 28 - Dec 29
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
Exterior
Best Western Annapolis

Best Western Annapolis

Best Western Annapolis
2.5 star property
7.8 out of 10, Good, (1004)
"Parking was safe and free. Staff from breakfast did good service although breakfast was the same for 3 days. Location was perfect."
Canada
Ermelita
$71 nightly
The price is $81
Dec 28 - Dec 29
Total with taxes and fees
Best Western Annapolis
Exterior
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
9.0 out of 10, Wonderful, (1002)
"Clean hotel, solid breakfast, and great staff. Beds are comfortable and rooms are up to date and quiet."
United States
Paul
$95 nightly
The price is $109
Jan 4 - Jan 5, 2026
Total with taxes and fees
Country Inn & Suites by Radisson, Annapolis, MD
Balcony view
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
9.4 out of 10, Exceptional, (360)
"Courteous and helpful staff. Comfortable, clean rooms in a beautiful setting. We enjoy our stays and always feel so welcomed!"
United States
Virginia
$120 nightly
The price is $132
Dec 14 - Dec 15
Total with taxes and fees
Knapps Narrows Marina & Inn
Exterior
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
8.6 out of 10, Excellent, (1008)
"Great value for stay with breakfast included "
United States
Aisling
$79 nightly
The price is $90
Dec 21 - Dec 22
Total with taxes and fees
Hilton Garden Inn Annapolis Downtown
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
$175 nightly
The price is $193
Jan 1 - Jan 2, 2026
Total with taxes and fees
Wylder Tilghman Island
View from property
St Michaels Inn

St Michaels Inn

St Michaels Inn
2.5 star property
8.2 out of 10, Very Good, (1000)
"clean and comfy, friendly staff"
United States
Tamara
$105 nightly
The price is $116
Dec 24 - Dec 25
Total with taxes and fees
St Michaels Inn
Exterior
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
7.8 out of 10, Good, (862)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
$85 nightly
The price is $94
Dec 21 - Dec 22
Total with taxes and fees
Quality Inn Grasonville near Kent Island
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

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, (932)
"It was very comfortable and clean"
United States
Maria
$87 nightly
The price is $97
Jan 3 - Jan 4, 2026
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Balcony
Rod 'N' Reel Resort

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
8.4 out of 10, Very Good, (1000)
"The hotel is beautiful I can’t wait for"
United States
Lynn
$138 nightly
The price is $151
Jan 2 - Jan 3, 2026
Total with taxes and fees
Rod 'N' Reel Resort
Exterior
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
8.8 out of 10, Excellent, (1002)
"Excellent from check in to check out, highly recommend!"
United States
Eric
$106 nightly
The price is $121
Jan 11 - Jan 12, 2026
Total with taxes and fees
Crowne Plaza Annapolis by IHG
Exterior
Historic Inns of Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1899)
"Great staff, comfortable beds, clean rooms and perfect location "
United States
Dawn
$164 nightly
The price is $187
Dec 21 - Dec 22
Total with taxes and fees
Historic Inns of Annapolis
Exterior
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
8.2 out of 10, Very Good, (1000)
"Clean room, fast and easy check in, made to order breakfast options. "
United States
Michael
$74 nightly
The price is $85
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hilton Garden Inn Annapolis
Exterior
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
8.0 out of 10, Very Good, (1000)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
$83 nightly
The price is $93
Dec 22 - Dec 23
Total with taxes and fees
Best Western Kent Narrows Inn
Exterior
Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
8.8 out of 10, Excellent, (179)
"Nice staff, clean room, comfortable bed. "
United States
Jayne
$84 nightly
The price is $96
Dec 19 - Dec 20
Total with taxes and fees
Candlewood Suites Annapolis by IHG
Exterior
Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
9.0 out of 10, Wonderful, (165)
"Beautiful and very modern, breakfast was great"
United States
Dominic
$110 nightly
The price is $125
Dec 17 - Dec 18
Total with taxes and fees
Fairfield Inn & Suites By Marriott Annapolis
Marina
Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
9.4 out of 10, Exceptional, (470)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
$149 nightly
The price is $170
Dec 28 - Dec 29
Total with taxes and fees
Anchored Inn at Hidden Harbour Marina
Exterior
Comfort Inn Conference Center

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
9.2 out of 10, Wonderful, (1001)
"It had good parking and restaurant in the hotel with good prices."
United States
Patrick
$99 nightly
The price is $112
Dec 15 - Dec 16
Total with taxes and fees
Comfort Inn Conference Center
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Beautiful area! Loved the room! We took a taxi from the airport, it was nice to not have to worry about parking."
Amy 3-night trip
Posted 1 day ago
Historic Inns of Annapolis

Find out more about Shady Side

Shady Side Chalets information

Number of reviews
14,992
Accommodation
0 Chalets
Lowest Price
$81
Highest Price
$467

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