A river with boats, a marina, and a town with houses and buildings.

Holiday Homes in Shady Side

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Check prices for these dates

In two weeks
31 July - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Shady Side holiday homes

Terrace/patio

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 Access
Shady Side
The price is AU$520
includes taxes & fees
23 July - 24 July
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Interior

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."
United States
Michelle H.
The price is AU$867
includes taxes & fees
29 July - 30 July
Sunset Cottage - West River Access and Views!
Coffee/tea maker, fridge, microwave, oven

Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.4 out of 10, Exceptional, (13 reviews)
"Highly recommend this property! Great location. Place is clean and host was very accommodating."
United States
Abi O.
The price is AU$360
includes taxes & fees
28 July - 29 July
Cute, Cozy 2-bedroom house near Annapolis with water access
Exterior

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, (47 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."
United States
Brian
The price is AU$443
includes taxes & fees
19 July - 20 July
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Coffee/tea maker, fridge, microwave, oven

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (8 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is AU$880
includes taxes & fees
2 Aug - 3 Aug
Renovated Bungalow | Walk to Beach | Dog-Friendly
Coffee/tea maker, fridge, microwave, oven

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is AU$1,009
includes taxes & fees
19 July - 20 July
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
TV, offices

Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (4 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is AU$1,000
includes taxes & fees
21 July - 22 July
Family Home on Mayo Peninsula | Deck | Sleeps 10
Beach nearby, sun-loungers, beach towels

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (16 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is AU$1,031
includes taxes & fees
22 July - 23 July
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Beach nearby

Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (22 reviews)
"Although the house itself could use some maintenance, our stay was very comfortable. The rooms were spacious and it had all the amenities we needed. "
United States
Donovan B.
The price is AU$719
includes taxes & fees
13 Aug - 14 Aug
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Interior

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (40 reviews)
"Just was very responsive to all requests and inquiries."
United States
Vesta M.
The price is AU$529
includes taxes & fees
27 July - 28 July
Large 2 bedroom house with private parking in a nice neighborhood
Exterior

Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is AU$644
includes taxes & fees
18 July - 19 July
Plum Point Cottage #17
Living area

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is AU$912
includes taxes & fees
16 Aug - 17 Aug
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Exterior

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (40 reviews)
"Great place to stay, very private. Plenty of room for big groups. Would definitely book again, when in the area. "
United States
Handy M.
The price is AU$502
includes taxes & fees
3 Aug - 4 Aug
Charming Coastal/Country Home w/3 Acres & Sauna!
Outdoor dining

Waterfront Escape with Pool Nature Lover Paradise

Waterfront Escape with Pool Nature Lover Paradise
Stevensville
10.0 out of 10, Exceptional, (1 review)
"Great spot! Amazing amount of room. Great communication in ease of check-in"
United States
Jeffrey T.
The price is AU$1,719
includes taxes & fees
19 July - 20 July
Waterfront Escape with Pool Nature Lover Paradise
Microwave, oven, stovetop, dishwasher

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.4 out of 10, Very good, (6 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is AU$840
includes taxes & fees
27 July - 28 July
Fabulous 5-bedroom house with AC in charming Annapolis
Outdoor dining

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel 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. "
United States
Jen M.
The price is AU$1,223
includes taxes & fees
20 July - 21 July
Charming Annapolis WaterVIEW Home
Dining

Chic retreat steps to Water, Piers & Waterfront Park

Chic retreat steps to Water, Piers & Waterfront Park
Deale
10.0 out of 10, Exceptional, (1 review)
"This place is beautiful, and big. The back yard is nice. We played games out back and had a cookout. Walking distance to the pier and a playground. The"
United States
Jamie C.
Chic retreat steps to Water, Piers & Waterfront Park
TV

Londontowne Rancher | 3BR | Near Waterfront

Londontowne Rancher | 3BR | Near Waterfront
Edgewater
7.0 out of 10, Good, (2 reviews)
"The house was much smaller then it originally appeared to be in the listing photos and what they had available was the bare minimum. The neighborhood was rowdy and there was screaming late into the night. The shower also sprayed water all over the floor and caused a massive puddle. The house was overall nice and clean but not worth the price that it was listed for. A hotel would have much better accommodated our needs. "
United States
rebekah h.
The price is AU$1,007
includes taxes & fees
3 Aug - 4 Aug
Londontowne Rancher | 3BR | Near Waterfront
Dining

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is AU$847
includes taxes & fees
21 July - 22 July
Historic Row Home in Downtown Annapolis
Outdoor dining

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (37 reviews)
"Everything was as expected, lovely spot even with lots of snow and ice!"
United States
Becky S.
The price is AU$1,409
includes taxes & fees
31 July - 1 Aug
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
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

Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

10/10 Excellent
"Nice Staffs, Nice hotel and Clean hotel!! We went the night of the r&b tour and surprisely it was quiet all night. Definitely would return when football season is back… thank you!! Other thing I also like they have security that walks around the premises to make sure our cars, the staffs, the customers are safe."
Sonthi 1-night trip
Posted 1 hour ago
Comfort Inn Largo-Washington DC East

Find out more about Shady Side

Shady Side Holiday Homes information

Number of reviews
262
Accommodation
590 Holiday Homes
Lowest Price
AU$360
Highest Price
AU$1,719