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Compare 634 Vacation Homes in Shady Side with updated reviews, rates, and availability.

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (212)
"The house was absolutely perfect for our USNA Reunion. About 10 steps to Gate 1 and just a few more to the heart of downtown made it a weekend we will remember. The host was responsive and accommodated our requests and was very kind. I would definitely stay here again."
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.6 out of 10, Exceptional, (74)
"Nothing like home away from home!! Very comfortable home. Thank you. "
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (52)
"Cute as a button. Very, very clean, kitchen has everything, living room very comfortable for us 4 adults. Fenced yard was perfect for our furry companion. Excellent location-quiet neighborhood, easy walk to beach and restaurants.Host is very prompt responding to any inquiry. You won’t regret this rental!!"
The Blue Crab Beach House - Free beach passes

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (182)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

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

9.6 out of 10, Exceptional, (27)
"Nice and peaceful stay for a quick local getaway. "
The price is SAR 304
SAR 982 total
includes taxes & fees
22 Apr - 23 Apr
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Modern Waterfront House with amazing views of the ChesapeakeBay!

Modern Waterfront House with amazing views of the ChesapeakeBay!

Historic Annapolis Home 1.5 blocks from center of town.

9.8 out of 10, Exceptional, (35)
"Great wx and weekend visit to the Naval Academy. Walking distance to everything and neighborhood was a nice getaway from main street "
Historic Annapolis Home 1.5 blocks from center of town.

Sweet Bamboo Beach Cottage

10.0 out of 10, Exceptional, (73)
"Needed a little quiet time, and the fresh air. Had a nice time. The house is clean,stocked with basic essentials. The beds are comfortable, that is super important to me, I also enjoyed the color choices and decorations. Tracy was prompt and thorough. I’d stay again . "
Sweet Bamboo Beach Cottage

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (88)
"Ritchie, our host was extremely accommodating. Home looked exactly like the pictures. Very clean and comfortable. Water front! Many good restaurants within walking distance."
Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (34)
"Great location with two parking spots and a small yard. Great for family vacation. "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

2.0 star property
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

Steps to USNA Gate 3 at historic Gatehouse, on-site parking

2.5 star property
10.0 out of 10, Exceptional, (5)
"A great location and plenty of room for visiting groups to be in and out. Clean and well provisioned. Parking was a great feature as well."
Steps to USNA Gate 3 at historic Gatehouse, on-site parking

PERFECT LOCATION in the heart of history

10.0 out of 10, Exceptional, (197)
"Charming Annapolis house with a great location downtown. Very spacious and clean. Will definitely be staying here again! "
PERFECT LOCATION in the heart of history

Bay Breeze - Charming 3BR Waterfront Home on the Chester River

10.0 out of 10, Exceptional, (1)
"As advertised. Great views, dock and decks. Inside is modern, functional and very clean. No complaints whatsoever."
Bay Breeze - Charming 3BR Waterfront Home on the Chester River

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (46)
"Exactly as described. Appreciated coffee & cream upon arrival too."
The Lazy Crab Beach House - Free beach passes

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (34)
"Clean, Spacious, and exactly as advertised! "
The price is SAR 263
SAR 924 total
includes taxes & fees
20 Apr - 21 Apr
Relax on Kent Island in 3 Bedroom Home w/Waterview

The Cottage

10.0 out of 10, Exceptional, (4)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is SAR 732
SAR 1,429 total
includes taxes & fees
20 Apr - 21 Apr
The Cottage

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

9.8 out of 10, Exceptional, (40)
"Our group of longtime friends from different states wanted a convenient location to meet for a weekend getaway. The Eastern Shore was a good location and this property was a wonderful and comfortable place for our group. The house was spacious and had plenty of areas for members of the group to enjoy all together or in smaller conversation groups. Our group meals were easy to prepare in the large and well-equipped kitchen. The dining room easily accommodated our group for our dinners and the...
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

7 mins away from Downtown Annapolis

9.8 out of 10, Exceptional, (16)
"Loved the house, we were glad to be able to book it on short notice for a large group! Beds were insanely comfortable, and the house had everything we needed. It was clean, comfortable, and a fantastic location. Only downside is that the common areas (living room/kitchen/dining area) are a bit small if you have a larger group (8). Overall a great stay and would stay again!!"
7 mins away from Downtown Annapolis

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

9.6 out of 10, Exceptional, (15)
"This property is perfect for a weekend getaway. The location is unbeatable, and the house is amazing! Clean, well-appointed and beautiful. The property manager was also wonderful to work with. You won't be disappointed."
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
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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Other property types in Shady Side

The Cottage

10.0 out of 10, Exceptional, (4)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is SAR 732
SAR 1,429 total
includes taxes & fees
20 Apr - 21 Apr
The Cottage

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (212)
"The house was absolutely perfect for our USNA Reunion. About 10 steps to Gate 1 and just a few more to the heart of downtown made it a weekend we will remember. The host was responsive and accommodated our requests and was very kind. I would definitely stay here again."
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.6 out of 10, Exceptional, (74)
"Nothing like home away from home!! Very comfortable home. Thank you. "
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
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.