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Wireless Internet
Air conditioning
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Balcony or terrace
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Cot available
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Towels provided
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Private fishing lake or river
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Beach or lakeside relaxation
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Golf course on site or within 15 min walk
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106 Houses

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Serene Waterfront Apartment on Kent Island

Stevensville apartment

1 bedroom
1 bathroom

sleeps 2

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Price per night from

$229

Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can

Stevensville house

4 bedrooms
2 bathrooms

sleeps 12

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Price per night from

$803

Pool and Bay Views on wrap around deck in Kent Island

Stevensville house

3 bedrooms
3 bathrooms

sleeps 12

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Price per night from

$321

Private pier at Waterfront Kent Island home with Hot Tub (Open!)

Stevensville house

4 bedrooms
4 bathrooms

sleeps 8

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Price per night from

$416

Great rentals within 20 miles that match your search

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$861

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.

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Price per night from

$459

Beautiful Murray Hill Home (Annapolis)

Annapolis house

4 bedrooms
3 bathrooms

sleeps 9

“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies. We certainly will attempt to stay at this house again if we ever return to annapolis.

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Price per night from

$488

Vintage Bungalow-cozy, walk to shops, water, free pkg.

Annapolis house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$476

KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12

Kent Island house

4 bedrooms
2 bathrooms

sleeps 12

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Price per night from

$1,951

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Chester house

4 bedrooms
3 bathrooms

sleeps 10

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Price per night from

$1,951

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms
3 bathrooms

sleeps 10

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Price per night from

$1,148

Private Room - Creek Side

Glen Burnie townhouse

1 bedroom
1 bathroom

sleeps 1

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Price per night from

$58

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

4 bedrooms
3 bathrooms

sleeps 7

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Price per night from

$401

Great deal 4 Bedroom House Near the Ferry Park

Rock Hall house

5 bedrooms
2 bathrooms

sleeps 11

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Price per night from

$276

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

5 bedrooms
3 bathrooms

sleeps 8

Responds fast! avg. 38 minutes

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Price per night from

$2,295

CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood house

8 bedrooms
10 bathrooms

sleeps 12

Responds fast! avg. 38 minutes

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Price per night from

$2,868

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

6 bedrooms
6 bathrooms

sleeps 12

Responds fast! avg. 38 minutes

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Price per night from

$2,295

Ferry Bridge House

Easton house

3 bedrooms
5 bathrooms

sleeps 6

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Price per night from

$798

Waterfront Getaway, Dock Your Boat and Play!

Mayo camper van

1 bedroom
1 bathroom

sleeps 6

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Price per night from

$343

London Towne Bungalow w/Loft

Edgewater bungalow

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$299

Captain Quarters - Eastport!

Annapolis house

4 bedrooms
3 bathrooms

sleeps 10

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Price per night from

$573

Fisher House - Downtown Annapolis!

Annapolis house

3 bedrooms
2 bathrooms

sleeps 9

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Price per night from

$683

Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

Chester house

4 bedrooms
2 bathrooms

sleeps 8

“Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we first contacted him about renting.

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Price per night from

$454