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Compare 3 Villas in Shady Side with updated reviews, rates, and availability.

Breathtaking Waterfront Estate
Breathtaking Waterfront Estate
10.0 out of 10, Exceptional, (70)
"We had a wonderful stay here. The house has a really functional kitchen so we were able to cook a lot of meals here. The pool was perfect for young swimmers (decent sized shallow end) and we loved hanging out on the dock, crabbing and kayaking. With plenty of adult bikes, we took a trip each morning to the playground too. We hope to be back!"
Breathtaking Waterfront Estate
LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12
Pool
LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12
LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12
Exquisite 14,000 sq ft Waterfront Mansion with Pool
Exterior
Exquisite 14,000 sq ft Waterfront Mansion with Pool
Exquisite 14,000 sq ft Waterfront Mansion with Pool
Spacious 4-bedroom villa in Bowie
Interior
Spacious 4-bedroom villa in Bowie
2.0 star property
Spacious 4-bedroom villa in Bowie
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

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Miscellaneous
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (20)
"Our group had an amazing time staying on this property. There are many areas inside the house as well as outside the house where you can gather with family and friends. It was very quick and easy to order Ubers/lyfts to the downtow Annapolis area whenever we needed. The house is also convientely located near a small shaping center less than a mile away. We would highly recommend this property!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Directly Across from Gate One & Steps from the Waterfront
Private rear courtyard
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (200)
"Incredible location! The process was easy and the house completely suited our needs! We would definitely stay again!"
Directly Across from Gate One & Steps from the Waterfront
Charming Annapolis WaterVIEW Home
3 covered balconies, a ground floor patio, and ceramic and propane grills.
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (48)
"This house was perfect for our group of friends especially with infants. Easy check in, comfortable beds and room for pack and plays. Water view is amazing. Definitely worth the rent and would be interested in coming back!"
Charming Annapolis WaterVIEW Home
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.