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
Sunset Cottage - West River Access and Views!
Sunset Cottage - West River Access and Views!Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
Michelle H.
The price is AED 1,308
AED 2,332 total
includes taxes & fees
30 Jul - 31 Jul
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
The price is AED 774
AED 1,531 total
includes taxes & fees
26 Aug - 27 Aug
Family Home on Mayo Peninsula | Deck | Sleeps 10
Family Home on Mayo Peninsula | Deck | Sleeps 10Edgewater
10.0 out of 10, Exceptional, (4 reviews)
"House was clean and comfortable. Great layout. "
Kristin G.
The price is AED 889
AED 2,525 total
includes taxes & fees
27 Jul - 28 Jul
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, (16 reviews)
"The perfect off-season get-away! "
Pamela B.
The price is AED 1,322
AED 2,558 total
includes taxes & fees
25 Aug - 26 Aug
Charming Annapolis WaterVIEW Home
Charming Annapolis WaterVIEW HomeArundel on the Bay
9.8 out of 10, Exceptional, (73 reviews)
"We enjoyed our stay! The property has a beautiful view of the bay. It was a perfect set up for our family of four. "
Jen M.
Renovated Bungalow | Walk to Beach | Dog-Friendly
Renovated Bungalow | Walk to Beach | Dog-FriendlyEdgewater
9.6 out of 10, Exceptional, (10 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
Diane D.
The price is AED 768
AED 2,119 total
includes taxes & fees
2 Aug - 3 Aug
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, (48 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
Brian
The price is AED 540
AED 1,266 total
includes taxes & fees
11 Aug - 12 Aug
Annapolis Retreat - 7 mins from downtown Annapolis!
Annapolis Retreat - 7 mins from downtown Annapolis!Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
Paul C.
The price is AED 680
AED 2,010 total
includes taxes & fees
18 Aug - 19 Aug
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
Private vacation homes
Aparthotels
Save an average of 15% on thousands of hotels when you're signed in
Top Shady Side Hotel Reviews
Country Inn & Suites by Radisson, Annapolis, MD
8/10 Good
