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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Shady Side holiday homes

A deck with outdoor furniture, a red door, and a house with windows.

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
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is AU$531
includes taxes & fees
21 Oct - 22 Oct
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

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)
"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$706
includes taxes & fees
10 Nov - 11 Nov
Sunset Cottage - West River Access and Views!
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

3. 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$618
includes taxes & fees
18 Oct - 19 Oct
3-bedroom house in Deale located on Bay many amenities and great views
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

4. 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, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is AU$474
includes taxes & fees
19 Oct - 20 Oct
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

5. 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)
"Our host Adam was wonderful and very communicative. We love the house and the location was just great. It was close to everything and had water views. We will certainly come back again."
United States
Rebecca B.
The price is AU$411
includes taxes & fees
19 Oct - 20 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

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

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is AU$1,064
includes taxes & fees
21 Oct - 22 Oct
Family Home on Mayo Peninsula | Deck | Sleeps 10
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

7. The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is AU$407
includes taxes & fees
16 Oct - 17 Oct
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A beach with chairs and a pier in the background.

8. 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, (19 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is AU$756
includes taxes & fees
19 Oct - 20 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 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$810
includes taxes & fees
18 Oct - 19 Oct
Renovated Bungalow | Walk to Beach | Dog-Friendly
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

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$836
includes taxes & fees
3 Nov - 4 Nov
Annapolis Retreat - 7 mins from downtown Annapolis!
A bunk bed with a wooden frame, white bedding, and a blue pillow with a floral design.

11. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (3 reviews)
"Warm and cozy- amazing home, beautiful area"
United States
Sodbileg
The price is AU$610
includes taxes & fees
18 Oct - 19 Oct
Rose Haven Coastal Cottage
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 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$401
includes taxes & fees
18 Oct - 19 Oct
Charming Coastal/Country Home w/3 Acres & Sauna!
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

13. 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, (40 reviews)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is AU$653
includes taxes & fees
9 Nov - 10 Nov
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A calm lake with a sandy shore, surrounded by trees and houses.

14. 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$1,108
includes taxes & fees
18 Oct - 19 Oct
Londontowne Home | Beach | 3BR
A spacious living room with a sofa set, a coffee table, and a chair. There is a painting on the wall and a window providing natural light.

15. 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$1,064
includes taxes & fees
19 Oct - 20 Oct
Londontowne Rancher | 3BR | Near Waterfront
A spacious living room with a high ceiling, large windows, and a ceiling fan.

16. The Harness Creek Retreat in Annapolis

The Harness Creek Retreat in Annapolis
Hillsmere
The price is AU$599
includes taxes & fees
18 Oct - 19 Oct
The Harness Creek Retreat in Annapolis
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

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

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (27 reviews)
"The property was very clean nice open kitchen and comfortable rooms . Very nice experience definitely recommend."
United States
Antonio
The price is AU$304
includes taxes & fees
19 Oct - 20 Oct
Cute, Cozy 2-bedroom house near Annapolis with water access
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

18. Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.8 out of 10, Excellent, (12 reviews)
"Very nice home. Definitely recommend!"
United States
Bob H.
The price is AU$714
includes taxes & fees
27 Oct - 28 Oct
Fabulous 5-bedroom house with AC in charming Annapolis
A modern kitchen with a central island, built-in oven, and microwave.

19. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.4 out of 10, Exceptional, (13 reviews)
"Great location, very clean, and the host was very responsive!"
United States
Heather B.
The price is AU$731
includes taxes & fees
21 Oct - 22 Oct
Cute bungalow blocks to Stadium
A dining area with a table, chairs, a bench, a chandelier, and a view into another room.

20. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
9.4 out of 10, Exceptional, (3 reviews)
"The location of this home is stellar! Every shop and restaurant is within walking distance. The home is super clean and charming. Tastefully furnished both in style and comfort. The kitchen was fully stocked. The bathrooms are updated and beautiful. The showers are fantastic! Eric was a gem to work with!"
United States
gina w.
The price is AU$797
includes taxes & fees
21 Oct - 22 Oct
Historic Row Home 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

10/10 Excellent
"Great rooom, really great service."
Brandon 1-night trip
Posted 2 hours ago
Rod 'N' Reel Resort

Find out more about Shady Side

Shady Side Holiday Homes information

Number of reviews
243
Accommodation
594 Holiday Homes
Lowest Price
AU$304
Highest Price
AU$1,108