Shady Side Vacation Rentals
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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)
"Would stay here again "
Thomas D.
The price is CA $214
CA $606 total
includes taxes & fees
Feb 22 - Feb 23
Sunset Cottage - West River Access and Views!
Sunset Cottage - West River Access and Views!Shady Side
The price is CA $217
CA $552 total
includes taxes & fees
Feb 16 - Feb 17
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)
"Great stay, would do it again."
Brandon D.
The price is CA $110
CA $361 total
includes taxes & fees
Feb 16 - Feb 17
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)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
Stephanie S.
The price is CA $110
CA $361 total
includes taxes & fees
Feb 18 - Feb 19
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)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
Joe C.
The price is CA $339
CA $569 total
includes taxes & fees
Feb 13 - Feb 14
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)
"Perfect place to spend quality time with our three adult children and their significant others. "
Malarkey F.
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)
"Amazing news out of the back.Great for kayaking.We brought our own kayaksAnd also use yoursThere were four of usWe also took a nice trip over to Saint Michael’s"
Sandy S.
The price is CA $356
CA $723 total
includes taxes & fees
Feb 15 - Feb 16
Annapolis Retreat - 7 mins from downtown Annapolis!
Annapolis Retreat - 7 mins from downtown Annapolis!Hillsmere
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
Paul C.
The price is CA $216
CA $705 total
includes taxes & fees
Feb 18 - Feb 19
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
Sonesta ES Suites Annapolis
10/10 Excellent
Find out more about Shady Side
Shady Side Vacation Homes information
Number of reviews | 325 |
|---|---|
Accommodation | 591 Vacation Homes |
Lowest Price | CA $361 |
Highest Price | CA $957 |
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