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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
Location Location! St Michaels-- In Town Cottage!
St. Michaels house
- 2 bedrooms
- 2 bathrooms
- sleeps 5
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$352
Waterfront Property, Kayaks, Private Dock, Near Town
St. Michaels house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
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$859
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$6,870
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
Responds fast! avg. 38 minutes
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$2,290
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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$2,863
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$796
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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$2,290
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$1,890
Great rentals within 20 miles that match your search
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
“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
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
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
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$1,145
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$682
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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
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$401
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$343
Bay Ridge house by Quiet Waters Park, Thomas Point Park
Annapolis apartment
- 2 bedrooms
- 1 bathroom
- sleeps 5
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$224
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis apartment
- 2 bedrooms
- 1 bathroom
- sleeps 6
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$224
Free parking Historic Union House Downtown with private patio
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
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$403
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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
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
Waterfront family resort Lodge with private pier, game room and bar
Centreville house
- 5 bedrooms
- 4 bathrooms
- sleeps 15
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$400
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$518
Popular Historic Firehouse fully renovated with Parking and Pet Friendly
Annapolis house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
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$465
Free Parking at Randall House in Downtown Annapolis
Annapolis house
- 4 bedrooms
- 4 bathrooms
- sleeps 11
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$729
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
Pool and Bay Views on wrap around deck in Kent Island
Stevensville house
- 3 bedrooms
- 3 bathrooms
- sleeps 12
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$321
Eastport Bungalow - Popular house Walk to Downtown & USNA
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 7
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$400
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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$359
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$639
Walk to Main Street from Waterfront Condo with pool and parking
Annapolis condo
- 2 bedrooms
- 2 bathrooms
- sleeps 7
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$407