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Chestertown Rentals

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age 0-16
9 Results

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Price: high to low

Number of reviews

9 Houses

Cottage On Kent

Chestertown cottage

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$229

Cozy & Spacious Chestertown Home

Chestertown house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 43 minutes

Price per night from

$411

Retreat at a quiet, water front cottage

Chestertown house

3 bedrooms / 3 bathrooms / sleeps 8

“A best kept secret!” I have had the pleasure of staying at Cliff Point many times. The view cannot be matched, water views more than 180 degrees, sunsets are stunning. But on top of that the house is so comfortable and charming, spacious and cozy. Charming, Chestertown is a short drive away if you would enjoy a Saturday morning at the farmers market, antiquing, or maybe you want to stay on the water and take a kayak out. This is a perfect place for a family vacation or romantic get away, you choose. But do choose to come to Cliff Point it is a best kept secret! I try to get here as often as time allows. And that is not often enough.

Price per night from

$346

Great rentals within 20 miles that match your search

Luxury Apartment with Private Entrance

Centreville apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$138

Lakeside Private Apartment

Wye Mills apartment

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$164

Sailors Crossing

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$432

Bayside Retreat

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$332

Love Point Waterfront

Kent Island house

3 bedrooms / 3 bathrooms / sleeps 12

“Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, answered all of our questions and concerns timely. Property (Interior): The property is really clean and very well maintained considering its age. I also feel that it is properly stocked with all the necessities. Property (Outdoor Space / View): We spend the majority of our time there outside. The deck / backyard area is very well maintained and stocked with adequate furniture. We used the gas grill every day of our stay. The dock is set up nicely for fishing including rod holders and a light for night fishing. The view from the dock is to die for, the Bay is so wide and the Bay Bridge is a nice backdrop to the view specially during sunset. Fishing: Fishing is the best I have ever experienced (compared to all other rentals I tried). I caught numerous species from the dock including Spot, White Perch and of course Striped Bass (Rockfish). I caught my biggest Rockfish ever from the dock there (39 inch fish, roughly 30 pounds) in April. Overall, I love the property, the view and the peaceful surroundings. A great bonus for me is the short one hour commute to get there. We will definitely be back to Love Point for an encore.

Price per night from

$288

Bay Cottage

Rock Hall house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$314

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