
Holiday Homes in Shady Side
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Our top choices for Shady Side holiday homes

1. Sunset Cottage - West River Access and Views!
Sunset Cottage - West River Access and Views!Shady Side
9.8 out of 10, Exceptional, (6 reviews)
The price is €381
includes taxes & fees
1 Dec - 2 Dec

2. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach AccessShady Side
9.0 out of 10, Wonderful, (2 reviews)
The price is €318
includes taxes & fees
9 Nov - 10 Nov

3. 3-bedroom house in Deale located on Bay many amenities and great views
3-bedroom house in Deale located on Bay many amenities and great viewsDeale
10.0 out of 10, Exceptional, (1 review)
The price is €396
includes taxes & fees
13 Nov - 14 Nov

4. Beachside Oasis with Beach Passes & King Suite by A Haven Away
Beachside Oasis with Beach Passes & King Suite by A Haven AwayNorth Beach
10.0 out of 10, Exceptional, (25 reviews)
The price is €279
includes taxes & fees
1 Dec - 2 Dec

5. Family Home on Mayo Peninsula | Deck | Sleeps 10
Family Home on Mayo Peninsula | Deck | Sleeps 10Edgewater
10.0 out of 10, Exceptional, (6 reviews)
The price is €621
includes taxes & fees
11 Nov - 12 Nov

6. Renovated Bungalow | Walk to Beach | Dog-Friendly
Renovated Bungalow | Walk to Beach | Dog-FriendlyEdgewater
9.6 out of 10, Exceptional, (14 reviews)
The price is €457
includes taxes & fees
8 Nov - 9 Nov

7. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community BeachArundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
The price is €413
includes taxes & fees
9 Nov - 10 Nov

8. The Cozy Crab- Your Charming Haven in Lovely North Beach!
The Cozy Crab- Your Charming Haven in Lovely North Beach!North Beach
9.6 out of 10, Exceptional, (30 reviews)
The price is €276
includes taxes & fees
4 Dec - 5 Dec

9. Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Relax on Kent Island in a 4 Bedroom Home w/Waterview!Stevensville
9.8 out of 10, Exceptional, (57 reviews)
The price is €308
includes taxes & fees
23 Nov - 24 Nov

10. Annapolis Retreat - 7 mins from downtown Annapolis!
Annapolis Retreat - 7 mins from downtown Annapolis!Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
The price is €488
includes taxes & fees
11 Nov - 12 Nov

11. Londontowne Home | Beach | 3BR
Londontowne Home | Beach | 3BREdgewater
9.4 out of 10, Exceptional, (3 reviews)
The price is €606
includes taxes & fees
8 Nov - 9 Nov

12. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, RestaurantsNorth Beach
10.0 out of 10, Exceptional, (40 reviews)

14. Charming Coastal/Country Home w/3 Acres & Sauna!
Charming Coastal/Country Home w/3 Acres & Sauna!Stevensville
9.8 out of 10, Exceptional, (50 reviews)
The price is €269
includes taxes & fees
9 Nov - 10 Nov

15. Londontowne Rancher | 3BR | Near Waterfront
Londontowne Rancher | 3BR | Near WaterfrontEdgewater
7.0 out of 10, Good, (2 reviews)
The price is €641
includes taxes & fees
30 Nov - 1 Dec

16. Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and DowntownHomewood
9.8 out of 10, Exceptional, (10 reviews)
The price is €501
includes taxes & fees
17 Nov - 18 Nov

17. Fabulous 5-bedroom house with AC in charming Annapolis
Fabulous 5-bedroom house with AC in charming AnnapolisAnnapolis
8.8 out of 10, Excellent, (16 reviews)
The price is €378
includes taxes & fees
17 Nov - 18 Nov

18. 5 bedroom house with EV charger Near Downtown Annapolis
5 bedroom house with EV charger Near Downtown AnnapolisEastport
10.0 out of 10, Exceptional, (2 reviews)
The price is €545
includes taxes & fees
15 Nov - 16 Nov

19. Cute, Cozy 2-bedroom house near Annapolis with water access
Cute, Cozy 2-bedroom house near Annapolis with water accessHerald Harbor
9.8 out of 10, Exceptional, (31 reviews)
The price is €180
includes taxes & fees
15 Nov - 16 Nov

20. Mins to Historic Downtown Annapolis - Parking
Mins to Historic Downtown Annapolis - ParkingAnnapolis
10.0 out of 10, Exceptional, (6 reviews)
The price is €419
includes taxes & fees
9 Nov - 10 Nov
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

Country Inn & Suites by Radisson, Annapolis, MD
10/10 Excellent
Find out more about Shady Side
Shady Side Holiday Homes information
Number of reviews | 304 |
|---|---|
Accommodation | 591 Holiday Homes |
Lowest Price | €180 |
Highest Price | €641 |
































































