Photo by Michelle Gonzalez

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Feb 14 - Feb 16
In two weeks
Feb 21 - Feb 23
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Mar 7 - Mar 9
In two months
Apr 4 - Apr 6

Browse Select Middletown Villas

Stunning waterfront villa with indoor pool and kids swing set and play area.
Spa

Stunning waterfront villa with indoor pool and kids swing set and play area.

9.8 out of 10, Exceptional, (13)
"The house was beautiful. We enjoyed the pool. The kitchen was wonderful. We did wish we could warm up the house a little more. We loved that the house had so many bathrooms. The only improvement would be to state that there are 5 bedrooms with en-suites."
Stunning waterfront villa with indoor pool and kids swing set and play area.
Five Bedroom Villa & Pool on North East Harbor
Terrace/patio

Five Bedroom Villa & Pool on North East Harbor

10.0 out of 10, Exceptional, (7)
"Great location, very easy to get to, in a nice quiet neighborhood. Well appointed kitchen, huge amount of space for visiting or needing a quiet area to read. Immaculate! We were here for a wedding, but it's so beautiful, we'd like to return for a vacation! Our host Maia, was great to deal with, very responsive to questions and entry information etc."
Five Bedroom Villa & Pool on North East Harbor
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 Middletown

New Construction townhome close to everything downtown w/transparent pricing
Interior

New Construction townhome close to everything downtown w/transparent pricing

9.8 out of 10, Exceptional, (15)
"Beautiful home. Lisa was so lovely to specially set up a room for my 86 year old mother! We would not hesitate to stay again!!"
The price is CA $236
CA $294 total
includes taxes & fees
Feb 12 - Feb 13
New Construction townhome close to everything downtown w/transparent pricing
Beachfront Sunsets on the Water at Oakwood Beach
On the beach, sun loungers, beach towels

Beachfront Sunsets on the Water at Oakwood Beach

10.0 out of 10, Exceptional, (31)
"We had a nice visit to this beautiful, waterfront home, and appreciated the host very much. The views from the beach were lovely. Unfortunately, we were woken several times overnight one night by ships’ foghorns as they passed by- every few hours. Even the white noise machines (a thoughtful touch) didn’t help. Not sure how to predict when the ships come through, but we slept soundly the second of our two nights there. The area is otherwise very quiet- we barely saw anyone else around. The...
Beachfront Sunsets on the Water at Oakwood Beach
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Property grounds

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (22)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
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.