Holiday Homes in Shady Side

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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 €381
includes taxes & fees
10 Mar - 11 Mar
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
The price is €349
includes taxes & fees
11 Mar - 12 Mar
Sunset Cottage - West River Access and Views!
9.6 out of 10, Exceptional, (34 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is €220
includes taxes & fees
11 Mar - 12 Mar
Charming Coastal/Country Home w/3 Acres & Sauna!
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 €214
includes taxes & fees
10 Mar - 11 Mar
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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 €360
includes taxes & fees
10 Mar - 11 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 €274
includes taxes & fees
10 Mar - 11 Mar
Large 2 bedroom house with private parking in a nice neighborhood
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 €413
includes taxes & fees
10 Mar - 11 Mar
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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 €412
includes taxes & fees
7 Apr - 8 Apr
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 €448
includes taxes & fees
10 Mar - 11 Mar
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

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 €432
includes taxes & fees
10 Mar - 11 Mar
Cute bungalow blocks to Stadium
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 €373
includes taxes & fees
15 Mar - 16 Mar
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
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 €432
includes taxes & fees
22 Mar - 23 Mar
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
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 €386
includes taxes & fees
16 Mar - 17 Mar
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
9.6 out of 10, Exceptional, (5 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is €346
includes taxes & fees
30 Mar - 31 Mar
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
10.0 out of 10, Exceptional, (1 review)
"Host was wonderful! Enjoyed our weekend in a very clean, comfortable and peaceful place. Look forward to returning in warmer weather."
United States
Katherine P.
The price is €191
includes taxes & fees
16 Mar - 17 Mar
Cute, Cozy 2-bedroom house in near Annapolis with water access
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 €675
includes taxes & fees
9 Apr - 10 Apr
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Holiday Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
The price is €282
includes taxes & fees
24 Mar - 25 Mar
Cozy 2br home w/ parking in downtown Annapolis
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
The price is €316
includes taxes & fees
30 Mar - 31 Mar
Wright's Cottage- Pet's Welcome & EV Charging
9.0 out of 10, Wonderful, (4 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
London Towne Bungalow w/Loft - Walk to the Beach!
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.
Historic Row Home | Hot Tub - 1 Block from Gate 1!
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

Find out more about Shady Side

Shady Side Holiday Homes information

Number of reviews
13,548
Accommodation
591 Holiday Homes
Lowest Price
€80
Highest Price
€180