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$275
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$228
Great rentals within 20 miles that match your search
“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 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
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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$453
Vintage Bungalow-cozy, walk to shops, water, free pkg.
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
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$476
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
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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$802
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
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$1,145
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$801
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$400
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
Nice ambient 5BDR with fast WiFi near Airport & Casino
Riviera Beach house
- 5 bedrooms
- 3 bathrooms
- sleeps 12
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$572
Private Beach Access, Onsite Kayaks and Shared Boat Ramp
Chestertown house
- 4 bedrooms
- 3 bathrooms
- sleeps 10
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$258
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$670
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$274
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$252
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$572
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$682
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$687
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$395
Waterfront family resort Lodge with private pier, game room and bar
Centreville house
- 5 bedrooms
- 4 bathrooms
- sleeps 15
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$400
Free Parking and Hot Tub at Pet Friendly Annapolis-themed home
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
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$360
Parking at Stunning On Cloud 9 with private patio pet-friendly
Annapolis house
- 4 bedrooms
- 4 bathrooms
- sleeps 10
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$500
Spacious Townhouse 1 block to Capital Bldg, Parking Multiple gathering spaces
Annapolis house
- 3 bedrooms
- 4 bathrooms
- sleeps 6
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$378
Free parking Historic Union House Downtown with private patio
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
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$401
Free Parking at Randall House in Downtown Annapolis
Annapolis house
- 4 bedrooms
- 4 bathrooms
- sleeps 11
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$729
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$394
Historic Carriage House in the Heart of Downtown Annapolis
Annapolis house
- 2 bedrooms
- 2 bathrooms
- sleeps 6
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$343
Private pier and pool at this waterfront Chestertown home
Chestertown house
- 5 bedrooms
- 4 bathrooms
- sleeps 14
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$458
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
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
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
Annapolis house
- 2 bedrooms
- 2 bathrooms
- sleeps 5
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$338
Stay just steps from the Waterfront in the modern Historic Fleet's Inn
Annapolis house
- 2 bedrooms
- 2 bathrooms
- sleeps 4
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$405
2 parking spots and Walkable to Main Street at Seashell in the City
Annapolis house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
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$465
Eastport Bungalow - Popular house Walk to Downtown & USNA
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 7
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$400