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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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$1,118
Great rentals within 20 miles that match your search
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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$1,031
Vintage Bungalow-cozy, walk to shops, water, free pkg.
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
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$476
Waterfront Property, Kayaks, Private Dock, Near Town
St. Michaels house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
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$860
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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$1,950
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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$1,950
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
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$1,147
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$797
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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$2,294
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$458
Responds fast! avg. 38 minutes
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$2,294
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$573
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$1,548
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$802
Perfect Annapolis with Lots of Parking & Hot Tub
Annapolis townhouse
- 4 bedrooms
- 3 bathrooms
- sleeps 10
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$797
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$802
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$6,880
Pool and Bay Views on wrap around deck in Kent Island
Stevensville house
- 3 bedrooms
- 3 bathrooms
- sleeps 12
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$321
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$429
Private Waterfront Retreat with Pool, Hot Tub and Game Room
Tracys Landing house
- 5 bedrooms
- 4 bathrooms
- sleeps 14
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$727
Take your Leave of Absence around gardens with driveway parking
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 9
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$426
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$391
Eastport Gem - Popular house walk to Downtown & USNA
Annapolis house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
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$400
Luxury Waterfront home with private pier and guest house
Annapolis house
- 5 bedrooms
- 4 bathrooms
- sleeps 12
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$979
Walk to Main Street from Waterfront Condo with pool and parking
Annapolis condo
- 2 bedrooms
- 2 bathrooms
- sleeps 7
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$407
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$394
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 - Stone's throw from Annapolis City Dock with private back patio
Annapolis house
- 2 bedrooms
- 2 bathrooms
- sleeps 5
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$338
Hanover House across from USNA Gate 3 with private back patio
Annapolis house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
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$465
Private Waterview Estate with 4 bedroom Suites & Hot Tub
Shady Side house
- 6 bedrooms
- 7 bathrooms
- sleeps 14
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$429
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
Dog-friendly Shore Leave in waterfront Edgewater neighborhood with private patio
Edgewater house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
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$403
Still Available for 2024 Commissioning Week! Historic gem steps to USNA
Annapolis house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
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$465
All newly renovated Eastport Retreat - private back patio with parking
Annapolis house
- 6 bedrooms
- 6 bathrooms
- sleeps 15
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$785
Parking at Stunning On Cloud 9 with private patio pet-friendly
Annapolis house
- 4 bedrooms
- 4 bathrooms
- sleeps 10
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$500
Free Parking at Randall House in Downtown Annapolis
Annapolis house
- 4 bedrooms
- 4 bathrooms
- sleeps 11
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$729
New Luxury Lighthouse Inn with parking, private backyard, walkable to downtown
Annapolis house
- 4 bedrooms
- 4 bathrooms
- sleeps 12
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$500