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Check prices for these dates

In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec

Browse Select Shady Side Cottages

Our top choices for Shady Side cottages

6 Mi to Dtwn: Family-friendly Home in Annapolis!
Interior

6 Mi to Dtwn: Family-friendly Home in Annapolis!

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!
North Beach Cottage - Walk to Chesapeake Bay
Cottage (3 Bedrooms) | Interior

North Beach Cottage - Walk to Chesapeake Bay

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house condition was very cleran,beautiful. we appreciate the house owner's guidance&help. we made very good memories!"
North Beach Cottage - Walk to Chesapeake Bay
Waterfront North Beach Home ~ 2 Mi to Beach!
House (2 Bedrooms) | Interior

Waterfront North Beach Home ~ 2 Mi to Beach!

3.0 star property
Waterfront North Beach Home ~ 2 Mi to Beach!
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
House (4 Bedrooms) | Interior

Annapolis Vacation Home: 2 Mi to Quiet Waters Park

3.0 star property
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Cottage (2 Bedrooms) | Interior

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

3.0 star property
8.0 out of 10, Very good, (2)
"The water is well water and it stinks, water treatment could improve that. This is more in the woods than beachy. In a rundown area. Get some Damprid to cut down on musty smell. Cute decor."
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Exterior

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

3.0 star property
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Waterfront Annapolis Home: Fire Pit & Fishing Pier
House (3 Bedrooms) | Interior

Waterfront Annapolis Home: Fire Pit & Fishing Pier

3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Tilghman Island Retreat By Knapps Narrows!
House (2 Bedrooms) | Front of property

Tilghman Island Retreat By Knapps Narrows!

3.0 star property
Tilghman Island Retreat By Knapps Narrows!
Grasonville Home w/ Private Pool on the Water
House (3 Bedrooms) | Interior

Grasonville Home w/ Private Pool on the Water

3.0 star property
Grasonville Home w/ Private Pool on the Water
Annapolis Home Near Beach & Quiet Waters Park!
Terrace/patio

Annapolis Home Near Beach & Quiet Waters Park!

3.0 star property
Annapolis Home Near Beach & Quiet Waters Park!
Updated North Beach Cottage: Pet Friendly!
Cottage (3 Bedrooms) | Front of property

Updated North Beach Cottage: Pet Friendly!

3.0 star property
6.0 out of 10, (1)
"The property needs a severe cleaning. The floors were filthy. "
Updated North Beach Cottage: Pet Friendly!
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
House (1 Bedroom) | Interior

Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit

3.0 star property
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
Bayfront Maryland Retreat w/ Deck, Near Beaches!
House (3 Bedrooms) | Front of property

Bayfront Maryland Retreat w/ Deck, Near Beaches!

3.0 star property
Bayfront Maryland Retreat w/ Deck, Near Beaches!
Near Top Attractions: Deck Dining at Severn Home!
House (4 Bedrooms) | Interior

Near Top Attractions: Deck Dining at Severn Home!

3.0 star property
Near Top Attractions: Deck Dining at Severn Home!
Waterfront Home w/ Hot Tub in Bozman Village!
House (4 Bedrooms) | Interior

Waterfront Home w/ Hot Tub in Bozman Village!

3.0 star property
Waterfront Home w/ Hot Tub in Bozman Village!
Water-view Deale Home: Walk to Marina, Restaurants
House (5 Bedrooms) | Interior

Water-view Deale Home: Walk to Marina, Restaurants

3.0 star property
Water-view Deale Home: Walk to Marina, Restaurants
On-site Boat Dock: Queenstown Home w/ Pool & Yard!
House (5 Bedrooms) | Interior

On-site Boat Dock: Queenstown Home w/ Pool & Yard!

3.0 star property
On-site Boat Dock: Queenstown Home w/ Pool & Yard!
Coastal Edgewater Home w/ Private Hot Tub!
House (5 Bedrooms) | Interior

Coastal Edgewater Home w/ Private Hot Tub!

3.0 star property
Coastal Edgewater Home w/ Private Hot Tub!
Walk to Lake & Boat Ramp: Central Gem in Annapolis
House (4 Bedrooms) | Interior

Walk to Lake & Boat Ramp: Central Gem in Annapolis

3.0 star property
Walk to Lake & Boat Ramp: Central Gem in Annapolis
13 Mi to Annapolis: Dog-friendly Home w/ Fire Pit!
House (3 Bedrooms) | Interior

13 Mi to Annapolis: Dog-friendly Home w/ Fire Pit!

3.0 star property
13 Mi to Annapolis: Dog-friendly Home w/ Fire Pit!
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Relaxing "
William 2-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Shady Side

Find out more about Shady Side

Shady Side Cottages information

Number of reviews
3
Accommodation
29 Cottages
Lowest Price
Highest Price

Frequently asked questions

How much do cottages in Shady Side cost?
Cottages in Shady Side range between and per night. These retreats offer a chance to get reacquainted with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Shady Side with Expedia?
Reserving a cottage in Shady Side is as simple as deciding on your travel dates and choosing your ideal place for a getaway in nature. From upscale retreats to affordable stays and cottages that include perks like a pool, Expedia has something for all styles. As for epic deals? We've got them as well!
How can I find cheap cottages in Shady Side?
Expedia is here to help you locate cheap cottages in Shady Side. To book a fantastic stay in a few quick clicks, use our handy filter tool to refine your search results by amenities, star rating and budget.