
Search Vacation Homes in Shady Side
- 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 vacation homes

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady SideShady Side
10.0 out of 10, Exceptional, (4 reviews)
The price is ¥24,762
¥70,410 total
includes taxes & fees
Jan 26 - Jan 27

Sunset Cottage - West River Access and Views!
Sunset Cottage - West River Access and Views!Shady Side
The price is ¥27,829
¥65,443 total
includes taxes & fees
Jan 20 - Jan 21

Charming Coastal/Country Home w/3 Acres & Sauna!
Charming Coastal/Country Home w/3 Acres & Sauna!Stevensville
9.6 out of 10, Exceptional, (32 reviews)
The price is ¥11,954
¥40,327 total
includes taxes & fees
Jan 21 - Jan 22

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, (43 reviews)
The price is ¥8,368
¥35,856 total
includes taxes & fees
Jan 19 - Jan 20

Walk to Beach! King Bed & Free Beach Passes
Walk to Beach! King Bed & Free Beach PassesNorth Beach
10.0 out of 10, Exceptional, (17 reviews)
The price is ¥12,871
¥51,059 total
includes taxes & fees
Jan 20 - Jan 21

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 ¥39,530
¥66,708 total
includes taxes & fees
Jan 19 - Jan 20

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, (31 reviews)
The price is ¥15,828
¥64,627 total
includes taxes & fees
Jan 21 - Jan 22

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8Cambridge
10.0 out of 10, Exceptional, (14 reviews)
The price is ¥41,483
¥83,527 total
includes taxes & fees
Jan 20 - Jan 21
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 vacation 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

DoubleTree by Hilton Hotel Annapolis
10/10 Excellent
Find out more about Shady Side
Shady Side Vacation Homes information
Number of reviews | 308 |
|---|---|
Accommodation | 591 Vacation Homes |
Lowest Price | ¥35,856 |
Highest Price | ¥116,987 |















































































