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
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Shady Side holiday homes

Terrace/patio

1. 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
10.0 out of 10, Exceptional, (1 review)
"Jut as described. Easy in easy out. Great for a few days with the family."
United States
Joshua T.
The price is AU$351
includes taxes & fees
8 Sept - 9 Sept
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Interior

2. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Lovely place and neighborhood! "
United States
Marci M.
The price is AU$735
includes taxes & fees
8 Sept - 9 Sept
Sunset Cottage - West River Access and Views!
Exterior

3. 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, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is AU$380
includes taxes & fees
1 Sept - 2 Sept
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Living area

4. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is AU$711
includes taxes & fees
10 Sept - 11 Sept
3-bedroom house in Deale located on Bay many amenities and great views
Living area

5. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (5 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is AU$989
includes taxes & fees
1 Sept - 2 Sept
Family Home on Mayo Peninsula | Deck | Sleeps 10
Beach

6. 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)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is AU$485
includes taxes & fees
8 Sept - 9 Sept
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Private kitchen

7. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (12 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is AU$779
includes taxes & fees
2 Sept - 3 Sept
Renovated Bungalow | Walk to Beach | Dog-Friendly
Outdoor dining

8. 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)
"Such a great house! "
United States
Stephanie V.
The price is AU$559
includes taxes & fees
1 Sept - 2 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Marina

9. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
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$690
includes taxes & fees
1 Sept - 2 Sept
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Interior

10. 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!"
United States
Paul C.
The price is AU$846
includes taxes & fees
15 Sept - 16 Sept
Annapolis Retreat - 7 mins from downtown Annapolis!
Outdoor dining

11. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (76 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
The price is AU$993
includes taxes & fees
1 Sept - 2 Sept
Charming Annapolis WaterVIEW Home
Living area

12. 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$1,036
includes taxes & fees
14 Sept - 15 Sept
Londontowne Rancher | 3BR | Near Waterfront
Beach

13. Londontowne Home | Beach | 3BR

Londontowne Home | Beach | 3BR
Edgewater
9.4 out of 10, Exceptional, (3 reviews)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
The price is AU$1,040
includes taxes & fees
1 Sept - 2 Sept
Londontowne Home | Beach | 3BR
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is AU$435
includes taxes & fees
2 Sept - 3 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!
Living area

15. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is AU$910
includes taxes & fees
13 Sept - 14 Sept
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Exterior detail

16. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Historic District
10.0 out of 10, Exceptional, (5 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is AU$1,011
includes taxes & fees
7 Sept - 8 Sept
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Private kitchen

17. Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Private kitchen

18. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (10 reviews)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is AU$739
includes taxes & fees
1 Sept - 2 Sept
Cute bungalow blocks to Stadium
Private kitchen

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

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.6 out of 10, Exceptional, (20 reviews)
"Great stay! Very clean home in a quiet neighborhood. Easy drive to downtown, and there’s a local restaurant right down the street. We really enjoyed our stay!"
United States
Taylor C.
The price is AU$325
includes taxes & fees
8 Sept - 9 Sept
Cute, Cozy 2-bedroom house near Annapolis with water access
Marina

20. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (85 reviews)
"Great place to stay!! Very close to everything in Annapolis and able to walk everywhere."
United States
Matt S.
The price is AU$620
includes taxes & fees
8 Sept - 9 Sept
Cozy 2br home w/ parking in downtown Annapolis
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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

8/10 Good
"The resort was clean, and the rooms were modern, comfortable, and well maintained. There were several restaurants on the property, along with a mini casino, which provided plenty of dining and entertainment options. The staff was friendly and welcoming."
James 2-night trip
Posted 6 hours ago
Rod 'N' Reel Resort

Find out more about Shady Side

Shady Side Holiday Homes information

Number of reviews
296
Accommodation
590 Holiday Homes
Lowest Price
AU$325
Highest Price
AU$1,040