
Shady Side Vacation Rentals
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Our top choices for Shady Side vacation 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 CA $295
CA $620 total
includes taxes & fees
Dec 1 - Dec 2

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
9.4 out of 10, Exceptional, (3 reviews)
The price is CA $244
CA $511 total
includes taxes & fees
Nov 15 - Nov 16

3. Relax on Kent Island in 4 Bedroom Home w/Waterview
Relax on Kent Island in 4 Bedroom Home w/WaterviewStevensville
9.8 out of 10, Exceptional, (57 reviews)
The price is CA $120
CA $407 total
includes taxes & fees
Nov 15 - Nov 16

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 CA $125
CA $443 total
includes taxes & fees
Nov 15 - Nov 16

5. 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, (2 reviews)
The price is CA $257
CA $623 total
includes taxes & fees
Nov 15 - Nov 16

6. 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 CA $207
CA $446 total
includes taxes & fees
Nov 15 - Nov 16

7. 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 CA $94
CA $281 total
includes taxes & fees
Nov 15 - Nov 16

8. 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 CA $345
CA $960 total
includes taxes & fees
Nov 15 - Nov 16

9. 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 CA $275
CA $756 total
includes taxes & fees
Nov 15 - Nov 16

10. Charming Coastal/Country Home w/3 Acres & Sauna!
Charming Coastal/Country Home w/3 Acres & Sauna!Stevensville
9.8 out of 10, Exceptional, (51 reviews)
The price is CA $146
CA $438 total
includes taxes & fees
Nov 23 - Nov 24

11. 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, (41 reviews)
The price is CA $157
CA $563 total
includes taxes & fees
Nov 16 - Nov 17

12. 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 CA $300
CA $758 total
includes taxes & fees
Nov 30 - Dec 1

13. 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 CA $295
CA $673 total
includes taxes & fees
Nov 16 - Nov 17

14. Londontowne Home | Beach | 3BR
Londontowne Home | Beach | 3BREdgewater
9.4 out of 10, Exceptional, (3 reviews)
The price is CA $345
CA $1,010 total
includes taxes & fees
Nov 15 - Nov 16

15. Large 2 bedroom house with private parking in a nice neighborhood
Large 2 bedroom house with private parking in a nice neighborhoodArnold
9.4 out of 10, Exceptional, (44 reviews)
The price is CA $193
CA $447 total
includes taxes & fees
Nov 15 - Nov 16

16. The Harness Creek Retreat in Annapolis
The Harness Creek Retreat in AnnapolisHillsmere
10.0 out of 10, Exceptional, (1 review)
The price is CA $385
CA $605 total
includes taxes & fees
Nov 15 - Nov 16

17. Londontowne Rancher | 3BR | Near Waterfront
Londontowne Rancher | 3BR | Near WaterfrontEdgewater
7.0 out of 10, Good, (2 reviews)
The price is CA $411
CA $992 total
includes taxes & fees
Nov 30 - Dec 1

18. 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 CA $372
CA $856 total
includes taxes & fees
Nov 17 - Nov 18

19. Fabulous 5-bedroom house with AC in charming Annapolis
Fabulous 5-bedroom house with AC in charming AnnapolisAnnapolis
8.6 out of 10, Excellent, (18 reviews)
The price is CA $464
CA $660 total
includes taxes & fees
Nov 16 - Nov 17

20. Cute bungalow blocks to Stadium
Cute bungalow blocks to StadiumAdmiral Heights
9.4 out of 10, Exceptional, (13 reviews)
The price is CA $318
CA $822 total
includes taxes & fees
Nov 30 - Dec 1
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
8/10 Good
Find out more about Shady Side
Shady Side Vacation Homes information
Number of reviews | 380 |
|---|---|
Accommodation | 590 Vacation Homes |
Lowest Price | CA $281 |
Highest Price | CA $1,010 |
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