Hotels in Shady Side

Canary Pointe-A popular getaway for 2!

Shady Side, MD

10

Exceptional

272 reviews

Pet Friendly

Free WiFi

Air Conditioned

Free Parking

from

$160

/ night

Sunset Cottage

Exceptional

Free WiFi

Air Conditioned

Free Parking

from

$512

/ night

Otterspace at the beach

Shady Side, MD

Parking

Free WiFi

Free Parking

from

$233

/ night

Franklin At The Bay. Be one of the first to stay!

Exceptional

Pet Friendly

Free WiFi

Air Conditioned

Free Parking

from

$510

/ night

Bay Front Manor House

Churchton, MD

Parking

Free WiFi

Free Parking

Non-Smoking Rooms

from

$360

/ night

Grandma's Summer House Beverly Beach

Beverly Beach, MD

from

$526

/ night

Great for couples

Anchored Inn at Hidden Harbor

Superb

Enjoy a seasonal outdoor pool and complimentary breakfast at this charming hotel in Deale, Maryland, near Chesapeake Bay.

Pool

Parking

Free WiFi

Free Parking

from

$212

/ night

Coastal Waterfront 1 Bedroom Cottage

Hillsmere Shores, Annapolis, MD

10

Exceptional

220 reviews

Pool

Free WiFi

Air Conditioned

Free Parking

from

$543

/ night

”The Perch” - Hot Tub - Beach - Chesapeake Bay

Arundel on the Bay, Annapolis, MD

9.8

Exceptional

98 reviews

Pool

Pet Friendly

Free WiFi

Air Conditioned

from

$372

/ night

The Inn at Tacaro Estate

Superb

5-star

Pool

Parking

Free WiFi

from

$449

/ night

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

Arundel on the Bay, Annapolis, MD

Pet Friendly

Free WiFi

Gym & fitness facilities

Beach (Nearby)

from

$482

/ night

Edgewatermayo Getaway

Selby-on-the-Bay, MD

from

$517

/ night

Thomas Point Tranquility

Annapolis, MD

from

$1,106

/ night

SpringHill Suites by Marriott Annapolis

Parole, Annapolis, MD

8.7

Fabulous

1,004 reviews

Enjoy an indoor pool, hot tub, and complimentary breakfast in this modern Annapolis hotel.

Pool

Parking

Free WiFi

Pool Indoor

from

$135

/ night

Great for couples

Laurel Grove Inn on the South

Parole, Annapolis, MD

9.6

Exceptional

530 reviews

from

$188

/ night

Candlewood Suites Annapolis by IHG

Parole, Annapolis, MD

8.8

Fabulous

333 reviews

Comfortable hotel with a 24-hour fitness center and free parking, close to Annapolis Harbour Center.

Parking

Free WiFi

Free Parking

Non-Smoking Rooms

from

$110

/ night

A Little Piece of Paradise - Waterfront Home

Exceptional

Pet Friendly

Free WiFi

Air Conditioned

Free Parking

from

$494

/ night

Annapolis home, near Downtown

Exceptional

Free WiFi

Air Conditioned

Free Parking

from

$804

/ night

Cozy Annapolis Basement APT

Exceptional

Free WiFi

Air Conditioned

Free Parking

from

$203

/ night

Boutique Brick Beauty

Eastport, Annapolis, MD

9.9

Exceptional

23 reviews

Pet Friendly

Free WiFi

Air Conditioned

Free Parking

from

$381

/ night