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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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$1,119
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
Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths
Cambridge house
- 6 bedrooms
- 5 bathrooms
- sleeps 18
“Outstanding Vacation Rental” Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river during the day was wonderful. The house was clean and well furnished. The dining room table and table on the porch provided plenty of seating for meals. There was plenty of hot water for showers and clean-up after meals. The pool was clean and the river was awesome, with a gradual slope that was perfect for kids and adults. We used the crab traps provided and caught 2 dozen crabs that made a great contribution to dinner on Friday. Crabbing was best by the dock. We caught all but 3 crabs there, rather than out closer to the middle of the river. The AC on the ground floor stopped working on Tuesday, but one call to the owner and the repair team was on-site in less than 2 hours. The issue was resolved before noon on Wednesday. We have been renting vacation properties for years and issues crop up from time to time. We appreciated the quick response and resolution. The one recommendation we will make is to bring bug spray (mosquitos and horse flies). We anticipated it being right on the river, but if you haven't had that experience, you need to be prepared.
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$1,032
“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
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$1,148
Responds fast! avg. 38 minutes
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$2,296
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$401
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$798
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$458
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$1,550
Waterfront Property, Kayaks, Private Dock, Near Town
St. Michaels house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
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$861
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$190
Location Location! St Michaels-- In Town Cottage!
St. Michaels house
- 2 bedrooms
- 2 bathrooms
- sleeps 5
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$353
Luxury Waterfront - 40 Acre Estate - Swimming, Boating, Activities
Royal Oak manor house
- 25 bedrooms
- 25 bathrooms
- sleeps 50
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$7,460
Annapolis Charm™ Waterfront Chesapeake Bay Getaway - Private Pier - Near USNA
Cape Saint Claire house
- 2 bedrooms
- 1 bathroom
- sleeps 6
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$402
Chesapeake Bay Getaway™ | Waterfront Experience with Pier!
Edgewater house
- 2 bedrooms
- 1 bathroom
- sleeps 8
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$574
Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!
Chester house
- 4 bedrooms
- 3 bathrooms
- sleeps 12
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$459
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$683
Perfect Annapolis with Lots of Parking & Hot Tub
Annapolis townhouse
- 4 bedrooms
- 3 bathrooms
- sleeps 10
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$798
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$6,886
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$672
Cottage by the Bay on one level in family-friendly community
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
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$367
Popular Eastport Retreat - private back patio with parking and walk to USNA
Annapolis house
- 6 bedrooms
- 6 bathrooms
- sleeps 14
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$785
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
Modern and cozy Captain’s Crossing Cape house in West Annapolis
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
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$402
Hanover House across from USNA Gate 3 with private back patio
Annapolis house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
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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
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$429
Still Available for 2024 Commissioning Week! Luxury Eastport apartment with gour
Annapolis apartment
- 1 bedroom
- 1 bathroom
- sleeps 2
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$298
Pet-friendly Edgewater cottage with hot tub near waterfront!
Edgewater house
- 3 bedrooms
- 2 bathrooms
- sleeps 7
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$268
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$382
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
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$395
Popular Historic Firehouse fully renovated with Parking and Pet Friendly
Annapolis house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
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$465
Stay in USNA-themed dog-friendly home steps from Navy Stadium
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 11
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$465
Waterfront pier, putting green just minutes from downtown Annapolis
Riva house
- 4 bedrooms
- 4 bathrooms
- sleeps 10
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$725