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Match: Children under 5
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$229
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.
Match: Children under 5
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$452
“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.
Match: Children under 5
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$458
Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!
Chester house
- 4 bedrooms
- 3 bathrooms
- sleeps 12
Match: Children under 5
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$458
KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12
Kent Island house
- 4 bedrooms
- 2 bathrooms
- sleeps 12
Match: Children under 5
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$1,944
Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can
Stevensville house
- 4 bedrooms
- 2 bathrooms
- sleeps 12
Match: Children under 5
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$801
Match: Children under 5
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$228
Match: Children under 5
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$429
DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12
Chester house
- 4 bedrooms
- 3 bathrooms
- sleeps 10
Match: Children under 5
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$1,944
Pool and Bay Views on wrap around deck in Kent Island
Stevensville house
- 3 bedrooms
- 3 bathrooms
- sleeps 12
Match: Children under 5
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$321
Private pier at Waterfront Kent Island home with Hot Tub (Open!)
Stevensville house
- 4 bedrooms
- 4 bathrooms
- sleeps 8
Match: Children under 5
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$416
Great rentals within 20 miles that match your search
St. Michael's Premier in Town Summer Cottage now with private pool!
St. Michaels house
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Match: Children under 5
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$715
Waterfront Property, Kayaks, Private Dock, Near Town
St. Michaels house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
Match: Children under 5
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$858
“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.
Match: Children under 5
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$486
Vintage Bungalow-cozy, walk to shops, water, free pkg.
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Match: Children under 5
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$475
Match: Children under 5
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$1,144
Match: Children under 5
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$275
Match: Children under 5
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$399
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
St. Michaels house
- 6 bedrooms
- 6 bathrooms
- sleeps 12
Responds fast! avg. 38 minutes
Match: Children under 5
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$2,287
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
Match: Children under 5
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$2,859
Match: Children under 5
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$457
Match: Children under 5
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$401
Responds fast! avg. 38 minutes
Match: Children under 5
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$2,287
Match: Children under 5
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$441
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$629
Match: Children under 5
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$342
Match: Children under 5
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$298
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$571
Price per night from
$1,544
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis apartment
- 2 bedrooms
- 1 bathroom
- sleeps 6
Match: Children under 5
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$223
Match: Children under 5
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$315
Match: Children under 5
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$343
Match: Children under 5
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$681
Match: Children under 5
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$206
Match: Children under 5
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$441
Home Away From Home- 4 bedroom spacious home with great backyard space
Severna Park house
- 4 bedrooms
- 3 bathrooms
- sleeps 8
Match: Children under 5
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$458
Match: Children under 5
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$228
Match: Children under 5
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$189