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Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview
Wittman log cabin
- 5 bedrooms
- 5 bathrooms
- sleeps 10
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$1,117
Great rentals within 20 miles that match your search
“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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$488
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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$454
Vintage Bungalow-cozy, walk to shops, water, free pkg.
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
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$476
Responds fast! avg. 32 minutes
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$258
“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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$459
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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$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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$1,951
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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$803
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$1,148
Responds fast! avg. 38 minutes
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$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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$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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$2,295
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$798
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$402
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$631
Beautiful Waterfront Home, Private Pool and Water Amenities- Sleeps 16
Cambridge house
- 5 bedrooms
- 3 bathrooms
- sleeps 18
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$861
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$343
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$299
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$573
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$316
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$345
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$683
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$207
Waterfront Property, Kayaks, Private Dock, Near Town
St. Michaels house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
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$861
St. Michael's Premier in Town Summer Cottage now with private pool!
St. Michaels house
- 2 bedrooms
- 2 bathrooms
- sleeps 4
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$716
Luxury Waterfront - 40 Acre Estate - Swimming, Boating, Activities
Royal Oak manor house
- 25 bedrooms
- 25 bathrooms
- sleeps 50
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$7,440
Stay in USNA-themed dog-friendly home steps from Navy Stadium
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 11
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$465
Still Available for 2024 Commissioning Week! Historic gem steps to USNA
Annapolis house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
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$465
Private Waterfront Retreat with Pool, Hot Tub and Game Room
Tracys Landing house
- 5 bedrooms
- 4 bathrooms
- sleeps 14
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$727
Historic Carriage House in the Heart of Downtown Annapolis
Annapolis house
- 2 bedrooms
- 2 bathrooms
- sleeps 6
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$343
Pool and Bay Views on wrap around deck in Kent Island
Stevensville house
- 3 bedrooms
- 3 bathrooms
- sleeps 12
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$321
Waterfront pier, putting green just minutes from downtown Annapolis
Riva house
- 4 bedrooms
- 4 bathrooms
- sleeps 10
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$725
1 Block to USNA with Chapel Views big back patio and off-site parking!
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 7
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$465
Cottage by the Bay on one level in family-friendly community
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
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$367
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$518
Stay On the Waterfront in Edgewater custom-built chalet w private pier and hot t
Edgewater house
- 6 bedrooms
- 6 bathrooms
- sleeps 15
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$1,390
Steps to Main Street w View of the Capital private back patio & free off-site pa
Annapolis house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
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$324