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Private Waterview Estate with 4 bedroom Suites & Hot Tub
Shady Side house
- 6 bedrooms
- 7 bathrooms
- sleeps 14
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$429
Great rentals within 20 miles that match your search
Perfect Annapolis with Lots of Parking & Hot Tub
Annapolis townhouse
- 4 bedrooms
- 3 bathrooms
- sleeps 10
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$796
“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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$458
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
“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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$487
Waterfront Property, Kayaks, Private Dock, Near Town
St. Michaels house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
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$859
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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$1,947
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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$1,947
Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!
Chester house
- 4 bedrooms
- 3 bathrooms
- sleeps 12
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$458
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$1,145
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$189
Chesapeake Bay Getaway™ | Waterfront Experience with Pier!
Edgewater house
- 2 bedrooms
- 1 bathroom
- sleeps 8
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$573
Location Location! St Michaels-- In Town Cottage!
St. Michaels house
- 2 bedrooms
- 2 bathrooms
- sleeps 5
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$352
Responds fast! avg. 38 minutes
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$2,290
Luxury Waterfront - 40 Acre Estate - Swimming, Boating, Activities
Royal Oak manor house
- 25 bedrooms
- 25 bathrooms
- sleeps 50
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$7,443
Annapolis Charm™ Waterfront Chesapeake Bay Getaway - Private Pier - Near USNA
Cape Saint Claire house
- 2 bedrooms
- 1 bathroom
- sleeps 6
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$401
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$400
Modern and cozy Captain’s Crossing Cape house in West Annapolis
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
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$402
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$670
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$457
Eastport Bungalow - Popular house Walk to Downtown & USNA
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 7
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$400
Still Available for 2024 Commissioning Week! Serene waterfront sunsets in this A
Annapolis house
- 5 bedrooms
- 2 bathrooms
- sleeps 10
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$637
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$382
Waterfront Jolly Roger with Private Pier mins to Annapolis
Crownsville house
- 4 bedrooms
- 3 bathrooms
- sleeps 12
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$454
Available 2024 Commissioning Week 13 mins to USNA Big Family Space
Severna Park house
- 4 bedrooms
- 2 bathrooms
- sleeps 14
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$127
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$1,451
Free parking Historic Union House Downtown with private patio
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
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$401
Free Parking with private fenced-in backyard with pool table at Weekender
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
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$292
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$360
Free Parking and Hot Tub at Pet Friendly Annapolis-themed home
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
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$360
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$395
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 Historic Firehouse fully renovated with Parking and Pet Friendly
Annapolis house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
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$465
Pet-friendly Edgewater cottage with hot tub near waterfront!
Edgewater house
- 3 bedrooms
- 2 bathrooms
- sleeps 7
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$281
Hanover House across from USNA Gate 3 with private back patio
Annapolis house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
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$465
Eastport Gem - Popular house walk to Downtown & USNA
Annapolis house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
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$400
Still Available for 2024 Commissioning Week - just 12 minutes to USNA with Priva
Severna Park house
- 3 bedrooms
- 2 bathrooms
- sleeps 9
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$321
Spacious Townhouse 1 block to Capital Bldg, Parking Multiple gathering spaces
Annapolis house
- 3 bedrooms
- 4 bathrooms
- sleeps 6
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$378