Search Villas in Shady Side

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

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

Vacation Home in Shady Side

10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
The price is SAR 540
SAR 1,609 total
includes taxes & fees
3 Dec - 4 Dec
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
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, (1042)
"room was clean and quiet; parking was easy and safe. Very good welcome cookies too."
United States
Francisco
The price is SAR 229
SAR 262 total
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, (1013)
"Clean room, great staff, great breakfast "
United States
Susanne
The price is SAR 297
SAR 339 total
includes taxes & fees
28 Dec - 29 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, (1000)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is SAR 391
SAR 509 total
includes taxes & fees
4 Dec - 5 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, (929)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is SAR 297
SAR 330 total
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, (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 SAR 450
SAR 495 total
includes taxes & fees
14 Dec - 15 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, (1000)
"I had a lovely stay."
United States
Kalynn
The price is SAR 243
SAR 277 total
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, (1000)
"clean and comfy, friendly staff"
United States
Tamara
The price is SAR 388
SAR 427 total
includes taxes & fees
23 Dec - 24 Dec
St Michaels Inn
Exterior
Quality Inn

Quality Inn

2.5 star property
7.8 out of 10, Good, (858)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is SAR 319
SAR 354 total
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 SAR 459
SAR 523 total
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 SAR 405
SAR 578 total
includes taxes & fees
8 Dec - 9 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, (162)
"Beautiful and very modern, breakfast was great"
United States
Dominic
The price is SAR 443
SAR 505 total
includes taxes & fees
8 Dec - 9 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, (1000)
"Clean room, friendly staff"
United States
Jodi
The price is SAR 312
SAR 356 total
includes taxes & fees
28 Dec - 29 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 SAR 450
SAR 661 total
includes taxes & fees
1 Jan - 2 January 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)
"Clean room and friendly staff! "
United States
Silvia
The price is SAR 282
SAR 322 total
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, (1913)
"Excellent hotel Really nice staff Love the valet guys "
United States
ben
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 SAR 247
SAR 281 total
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, (1000)
"It had good parking and restaurant in the hotel with good prices."
United States
Patrick
The price is SAR 372
SAR 420 total
includes taxes & fees
8 Dec - 9 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 SAR 503
SAR 574 total
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.
View all properties

White Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shady Side Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Clean room, friendly staff"
Jodi 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Annapolis, MD