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Match: Waterfront
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$367
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
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.
Match: Waterfront
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$453
Waterfront Property, Kayaks, Private Dock, Near Town
St. Michaels house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
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$860
“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
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
Responds fast! avg. 38 minutes
Match: Waterfront
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$2,293
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
St. Michaels house
- 6 bedrooms
- 6 bathrooms
- sleeps 12
Responds fast! avg. 38 minutes
Match: Waterfront
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$2,293
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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$2,867
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$343
Price per night from
$1,548
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$316
Luxury Waterfront - 40 Acre Estate - Swimming, Boating, Activities
Royal Oak manor house
- 25 bedrooms
- 25 bathrooms
- sleeps 50
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$7,453
Cozy Cool Spring waterfront apartment with pier mins to Annapolis
Arnold apartment
- 1 bedroom
- 1 bathroom
- sleeps 4
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$177
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$204
Stunning waterfront home with deep water private pier minutes to Annapolis
Crownsville house
- 4 bedrooms
- 4 bathrooms
- sleeps 12
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$561
Private Waterfront Retreat with Pool, Hot Tub and Game Room
Tracys Landing house
- 5 bedrooms
- 4 bathrooms
- sleeps 14
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$727
Match: Waterfront
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$429
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
Private pier at Waterfront Kent Island home with Hot Tub (Open!)
Stevensville house
- 4 bedrooms
- 4 bathrooms
- sleeps 8
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$416
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
The Pool Opens May 9 - Stay poolside for 2024 Commissioning Week Pier & parking
Arnold house
- 4 bedrooms
- 3 bathrooms
- sleeps 10
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$355
Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the
Annapolis cottage
- 3 bedrooms
- 2 bathrooms
- sleeps 8
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$407
Luxury Waterfront home with private pier and guest house
Annapolis house
- 5 bedrooms
- 4 bathrooms
- sleeps 12
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$907
Waterfront pier, putting green just minutes from downtown Annapolis
Riva house
- 4 bedrooms
- 4 bathrooms
- sleeps 10
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$725
Cottage by the Bay on one level in family-friendly community
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
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$367
River Breezes with a private pier, parking and billiards room
Severna Park house
- 4 bedrooms
- 3 bathrooms
- sleeps 13
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$466
Available for 2024 Commissioning Week Waterfront home mins to USNA
Crownsville house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
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$361
Waterfront Jolly Roger with Private Pier mins to Annapolis
Crownsville house
- 4 bedrooms
- 3 bathrooms
- sleeps 12
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$454
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$1,451
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$229
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
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
Match: Waterfront
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$1,890
Annapolis Charm™ Waterfront Chesapeake Bay Getaway - Private Pier - Near USNA
Cape Saint Claire house
- 2 bedrooms
- 1 bathroom
- sleeps 6
Match: Waterfront
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$401