Shady Side Holiday Homes from £161: Search Holiday Homes in Shady Side

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

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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

Shady Side

David S.

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with a large window, a dishwasher, and a ceiling fan.

2. Sunset Cottage - West River Access and Views!

Shady Side

Michelle H.

includes taxes & fees

10 Nov - 11 Nov

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

Deale

includes taxes & fees

27 Oct - 28 Oct

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

North Beach

Johanna S.

includes taxes & fees

2 Nov - 3 Nov

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!

Stevensville

Anthony P.

includes taxes & fees

1 Nov - 2 Nov

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

Edgewater

Kristin G.

includes taxes & fees

26 Oct - 27 Oct

A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

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

Edgewater

Diane D.

includes taxes & fees

26 Oct - 27 Oct

A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

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

North Beach

James L.

includes taxes & fees

26 Oct - 27 Oct

An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

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

North Beach

Sarah

includes taxes & fees

30 Oct - 31 Oct

A beach with chairs and a pier in the background.

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

Arundel on the Bay

Pamela B.

includes taxes & fees

3 Nov - 4 Nov

A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

11. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

includes taxes & fees

9 Nov - 10 Nov

A calm lake with a sandy shore, surrounded by trees and houses.

12. Londontowne Home | Beach | 3BR

Edgewater

Sam A.

includes taxes & fees

27 Oct - 28 Oct

A lighthouse with a white exterior, a balcony, and a metal roof.

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

Stevensville

Michael V.

includes taxes & fees

26 Oct - 27 Oct

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.

14. Londontowne Rancher | 3BR | Near Waterfront

Edgewater

"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. "

rebekah h.

includes taxes & fees

22 Nov - 23 Nov

A two-story house with a porch, a front door, and a mailbox.

15. Rose Haven Coastal Cottage

North Beach

Sodbileg

includes taxes & fees

20 Nov - 21 Nov

An outdoor patio with a glass table and chairs, a large umbrella, and a house with multiple windows and a balcony.

16. The Harness Creek Retreat in Annapolis

Hillsmere

includes taxes & fees

28 Oct - 29 Oct

A spacious living room with a large sofa, a coffee table, and a chandelier. There is a kitchen in the background with a dining area.

17. Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Homewood

Dan B.

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

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

Annapolis

Bob H.

includes taxes & fees

3 Nov - 4 Nov

A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

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

Herald Harbor

Jax H.

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with a central island, built-in oven, and microwave.

20. Cute bungalow blocks to Stadium

Admiral Heights

Heather B.

includes taxes & fees

26 Oct - 27 Oct

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Top Shady Side Hotel Reviews

Best Western Annapolis

8/10 Good

"The room and lobby were incredibly clean. The staff was pleasant and helpful. Overall pleased with the stay. Only downside was that the flush lever of the toilet would get stuck on the lid of the tank. And the chain to the flapper valve likely needs to be shortened. Once I adjusted the lever and tank lid the problem was corrected."