Holiday Homes in Shady Side

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search 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 homes

10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
The price is AU$610
includes taxes & fees
3 Mar - 4 Mar
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
The price is AU$619
includes taxes & fees
8 Mar - 9 Mar
Sunset Cottage - West River Access and Views!
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 "
United States
Stephanie S.
The price is AU$345
includes taxes & fees
3 Mar - 4 Mar
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.6 out of 10, Exceptional, (34 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is AU$345
includes taxes & fees
4 Mar - 5 Mar
Charming Coastal/Country Home w/3 Acres & Sauna!
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. "
United States
Joe C.
The price is AU$580
includes taxes & fees
3 Mar - 4 Mar
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.4 out of 10, Exceptional, (36 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is AU$448
includes taxes & fees
3 Mar - 4 Mar
Large 2 bedroom house with private parking in a nice neighborhood
10.0 out of 10, Exceptional, (19 reviews)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is AU$434
includes taxes & fees
3 Mar - 4 Mar
Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is AU$745
includes taxes & fees
3 Mar - 4 Mar
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is AU$663
includes taxes & fees
3 Mar - 4 Mar
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is AU$733
includes taxes & fees
3 Mar - 4 Mar
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Holiday Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
9.8 out of 10, Exceptional, (11 reviews)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
United States
Kelly D.
The price is AU$786
includes taxes & fees
3 Mar - 4 Mar
Neptune by the Water - Pet Friendly Fenced Yard
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is AU$606
includes taxes & fees
18 Mar - 19 Mar
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
The price is AU$502
includes taxes & fees
9 Mar - 10 Mar
Wright's Cottage- Pet's Welcome & EV Charging
9.6 out of 10, Exceptional, (5 reviews)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
The price is AU$538
includes taxes & fees
30 Mar - 31 Mar
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Holiday Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is AU$731
includes taxes & fees
5 Mar - 6 Mar
Cute bungalow blocks to Stadium
10.0 out of 10, Exceptional, (8 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is AU$614
includes taxes & fees
16 Mar - 17 Mar
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
10.0 out of 10, Exceptional, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is AU$593
includes taxes & fees
15 Mar - 16 Mar
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is AU$709
includes taxes & fees
3 Mar - 4 Mar
Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is AU$994
includes taxes & fees
3 Mar - 4 Mar
Historic Row Home | Hot Tub - 1 Block from Gate 1!
9.8 out of 10, Exceptional, (9 reviews)
"Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around."
United States
Jeanie W.
The price is AU$699
includes taxes & fees
3 Mar - 4 Mar
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Shady Side Hotel Reviews

Find out more about Shady Side

Shady Side Holiday Homes information

Number of reviews
234
Accommodation
591 Holiday Homes
Lowest Price
AU$345
Highest Price
AU$994