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28 Saf. - 2 Rab. I

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7 Rab. I - 9 Rab. I

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21 Rab. I - 23 Rab. I

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18 Rab. II - 20 Rab. II

Compare 90 Vacation Homes in Ridgely with updated reviews, rates, and availability.

Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier

"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."

Chestertown Vacation Rental | 4BR | 4.5BA | 6 Steps Required | 3,232 Sq Ft

"An absolute stunning view from the four season enclosed porch. This beautiful home is well equiped and a perfect location for Fall and Winter hunting trips near Chestertown/Kennedyville. Plenty of rooms/bathrooms/beds. Highly recommend!!!"

"Clean and nice place to stay"

Waterfront with private pier and great views

"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "

"We just finished a great three day stay at this property. The place was spotless and the location to the towns of the eastern shore was perfect. Wonderful to look out and see the river lazily roll by. The"

"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...

The Twin Ponds Lodge sits on over 7 acres of private waterfront property.

"We had a great time. Place was unique and good for group get together. "

"This property is a phenomenal place to spend time with family and enjoy beautiful St. Michael’s. The house is well stocked and convenient to town. We’d love to come back. "

"Nice place "

"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "

"We truly loved our stay! The home was super comfortable and well stocked for making Thanksgiving dinner for 6. We loved just looking out at the geese, swans and blue herons ! Really lovely. We’ll be back!"

Grasonville Vacation Rental | 3BR | 2BA | Stairs Required for Access

"We started an annual tradition to rent this house with friends. Love the property, beautiful views and great location. Making great memories that will last a lifetime. Thank you for allowing us to use your beautiful home! :)"

"The apartment was perfect. Spotless, well maintained and equipped. The owners had coffee, fruit bowl and goodies waiting.I would highly recommend this charming and centrally located rental, it’s very likely we would stay here again.Thanks Lynda and Ron."

Master bedroom.. King-size bed and en-suite bathroom.

"Very friendly and helpful host and a great property. "

"This is the cutest place! Super clean and equipped to the max, everything we could possibly need was provided. The beds/linens are extremely comfortable. And our hostess was quick to respond to a problem with the heat. Highly recommend!"

Welcome to Langford Creek Estate- a beautiful waterfront estate with an extensive amenity list!

"The owners were very flexible with us and understanding when it came to a booking mistake on my end. The house is lovely and the property is absolutely gorgeous. The deck was picture perfect. Highly recommend for a getaway on the eastern shore!"

SAR 1,438 total

includes taxes & fees

28 Feb - 1 Mar

"Were cozy in the fabulous kitchen family room area.A fire would have been nice!"

"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...