Manage your B&B

B&B Shady Side

1 Bed and Breakfast in Shady Side City (Maryland, United States)

Our top selectionPrice: Low → HighPrice: High → LowBest rated

Accommodation type

Holiday home

Apartment

Luxury home

Bed & breakfast

Inn

Boat

More

Review score

General amenities

Free Wifi

Electric vehicle charging station

Garden

Pets allowed

Free parking

Sauna

More

Room Amenities

Private bathroom

Family room

Private entrance

Air conditioning

Bath

Private terrace

More

Accessibility

Entire unit located on ground floor

Upper floors accessible by elevator

Adults only

Accommodations just outside your destination

Near Shady Side

Flag House Inn - B&B Annapolis

Flag House Inn - B&B Annapolis

Direct reservation

(15.4 km from Shady Side)

Spectacular Location Two Bedroom State Circle Apartment - B&B Annapolis

Spectacular Location Two Bedroom State Circle Apartment - B&B Annapolis

Spectacular Location Two Bedroom State Circle Apartment

Direct reservation

(15.4 km from Shady Side)

1 Block to USNA Stadium: Modern Annapolis Home! - B&B Annapolis

1 Block to USNA Stadium: Modern Annapolis Home! - B&B Annapolis

1 Block to USNA Stadium: Modern Annapolis Home!

Direct reservation

(15.4 km from Shady Side)

Downtown Annapolis King George 3rd Floor Hideaway - B&B Annapolis

Downtown Annapolis King George 3rd Floor Hideaway - B&B Annapolis

Downtown Annapolis King George 3rd Floor Hideaway

Direct reservation

(15.5 km from Shady Side)

Downtown Annapolis King George 1st Floor Hideaway - B&B Annapolis

Downtown Annapolis King George 1st Floor Hideaway - B&B Annapolis

Downtown Annapolis King George 1st Floor Hideaway

Direct reservation

(15.5 km from Shady Side)

Historic Downtown Annapolis Gem Near USNA - B&B Annapolis

Historic Downtown Annapolis Gem Near USNA - B&B Annapolis

Historic Downtown Annapolis Gem Near USNA

Direct reservation

(15.5 km from Shady Side)

Charming brick home with patio, WiFi, AC, & WD - walk to everything - B&B Annapolis

Charming brick home with patio, WiFi, AC, & WD - walk to everything - B&B Annapolis

Charming brick home with patio, WiFi, AC, & WD - walk to everything

Direct reservation

(15.5 km from Shady Side)

Walk to the stadium, downtown, West St - close to everything - B&B Annapolis

Walk to the stadium, downtown, West St - close to everything - B&B Annapolis

Walk to the stadium, downtown, West St - close to everything

Direct reservation

(15.5 km from Shady Side)

1 Mi to Boardwalk: Convenient North Beach Apt! - B&B North Beach

1 Mi to Boardwalk: Convenient North Beach Apt! - B&B North Beach

1 Mi to Boardwalk: Convenient North Beach Apt!

Direct reservation

(15.6 km from Shady Side)

8 Bells Bungalow - Cozy, Stylish, Prime Location - B&B Annapolis

8 Bells Bungalow - Cozy, Stylish, Prime Location - B&B Annapolis

8 Bells Bungalow - Cozy, Stylish, Prime Location

Direct reservation

(16.1 km from Shady Side)

All Star Annapolis Retreat - Walk To Stadium - B&B Annapolis

All Star Annapolis Retreat - Walk To Stadium - B&B Annapolis

All Star Annapolis Retreat - Walk To Stadium

Direct reservation

(16.3 km from Shady Side)

Weems Creek Cottage, Annapolis Waterfront - B&B Annapolis

Weems Creek Cottage, Annapolis Waterfront - B&B Annapolis

Weems Creek Cottage, Annapolis Waterfront

Direct reservation

(16.6 km from Shady Side)

Pet-Friendly Cottage Walk to USNA Stadium - B&B Annapolis

Pet-Friendly Cottage Walk to USNA Stadium - B&B Annapolis

Pet-Friendly Cottage Walk to USNA Stadium

Direct reservation

(16.7 km from Shady Side)

Modern Gem Near Historic Annapolis & Naval Academy - B&B Annapolis

Modern Gem Near Historic Annapolis & Naval Academy - B&B Annapolis

Modern Gem Near Historic Annapolis & Naval Academy

Direct reservation

(17 km from Shady Side)

Exquisite & Serene 1 Bedroom, 1 Full Bath Apartment - B&B Upper Marlboro

Exquisite & Serene 1 Bedroom, 1 Full Bath Apartment - B&B Upper Marlboro

Exquisite & Serene 1 Bedroom, 1 Full Bath Apartment

Direct reservation

(19.2 km from Shady Side)

Adorable Beach Cottage w/ Hot Tub & Tropical Bar! - B&B Chesapeake Beach

Adorable Beach Cottage w/ Hot Tub & Tropical Bar! - B&B Chesapeake Beach

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

Chesapeake Beach

Direct reservation

(19.5 km from Shady Side)

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️ - B&B Stevensville

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️ - B&B Stevensville

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

Direct reservation

(20.5 km from Shady Side)

Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER! - B&B Annapolis

Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER! - B&B Annapolis

Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER!

Direct reservation

(20.9 km from Shady Side)

Tilghman Island Retreat By Knapps Narrows! - B&B Tilghman

Tilghman Island Retreat By Knapps Narrows! - B&B Tilghman

Tilghman Island Retreat By Knapps Narrows!

Direct reservation

(20.9 km from Shady Side)

Waterfront Annapolis Cottage: Fire Pit & Pier - B&B Annapolis

Waterfront Annapolis Cottage: Fire Pit & Pier - B&B Annapolis

Waterfront Annapolis Cottage: Fire Pit & Pier

Direct reservation

(20.9 km from Shady Side)

Baydream Believer - B&B Saint Michaels

Baydream Believer - B&B Saint Michaels

Baydream Believer

Direct reservation

(22 km from Shady Side)

Pet-Friendly Beach Getaway, Relax by the Bay! - B&B Annapolis

Pet-Friendly Beach Getaway, Relax by the Bay! - B&B Annapolis

Pet-Friendly Beach Getaway, Relax by the Bay!

Direct reservation

(22.1 km from Shady Side)

Dragonfly Cove - B&B Bozman

Dragonfly Cove - B&B Bozman

Direct reservation

(22.3 km from Shady Side)

The Pool Loft at Poplar Hill - B&B Annapolis

The Pool Loft at Poplar Hill - B&B Annapolis

The Pool Loft at Poplar Hill

Direct reservation

(22.4 km from Shady Side)

Discover unique B&B destinations

Subscribe to our newsletter

United States
Maryland
Shady Side

Bedandbreakfast.eu

Service & Contact
About us
Travel inspiration

B&B hosts

Manage your B&B
List your B&B
Starting a B&B
FAQ
Must reads for B&B Innkeepers

Popular Destinations

Bed & Breakfast Edinburgh
Bed & Breakfast Dublin
Bed & Breakfast London
Bed & Breakfast Paris

English

Deutsch Español Français Italiano Nederlands

© 2026 Bedandbreakfast.eu