
Shady Side Holiday Rentals
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Shady Side holiday rentals

Sunset Cottage - West River Access and Views!
Sunset Cottage - West River Access and Views!Shady Side
10.0 out of 10, Exceptional, (4 reviews)
The price is HK$2,422
HK$4,446 total
includes taxes & fees
16 Jun - 17 Jun

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront ViewsArnold
9.6 out of 10, Exceptional, (10 reviews)
The price is HK$1,555
HK$3,515 total
includes taxes & fees
16 Jun - 17 Jun

Sailboat Experience in Annapolis
Sailboat Experience in AnnapolisParole
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,686
HK$2,147 total
includes taxes & fees
4 Jun - 5 Jun

Waterfront Unit | Dock, Kayaks & SUPs Included
Waterfront Unit | Dock, Kayaks & SUPs IncludedEdgewater
10.0 out of 10, Exceptional, (3 reviews)
The price is HK$1,520
HK$3,627 total
includes taxes & fees
31 May - 1 Jun

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, (45 reviews)
The price is HK$853
HK$2,259 total
includes taxes & fees
2 Jun - 3 Jun

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.Grasonville
9.6 out of 10, Exceptional, (12 reviews)
The price is HK$1,959
HK$3,281 total
includes taxes & fees
1 Jun - 2 Jun

Charming Coastal/Country Home w/3 Acres & Sauna!
Charming Coastal/Country Home w/3 Acres & Sauna!Stevensville
9.6 out of 10, Exceptional, (35 reviews)
The price is HK$970
HK$2,382 total
includes taxes & fees
3 Jun - 4 Jun

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, (40 reviews)
The price is HK$987
HK$2,474 total
includes taxes & fees
7 Jun - 8 Jun
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.
Find holiday rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Shady Side Hotel Reviews

Historic Inns of Annapolis
8/10 Good
Find out more about Shady Side
Search for holiday rentals in Shady Side on Expedia! You can easily find your home rentals, villas, holiday apartments in Shady Side using one of the methods below:
- View our selection of featured holiday rentals in Shady Side
- Use the map to find apartments and other holiday homes in the Shady Side neighbourhood you prefer
- Enter your travel dates to view the best deals on holiday rentals in Shady Side while they last
Look no further and take a look at our great range of rental properties in Shady Side!
















































































