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Price per night from
$6,870
Great rentals within 20 miles that match your search
St. Michael's Premier in Town Summer Cottage now with private pool!
St. Michaels house
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Price per night from
$716
Waterfront Property, Kayaks, Private Dock, Near Town
St. Michaels house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
Price per night from
$859
Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview
Wittman log cabin
- 5 bedrooms
- 5 bathrooms
- sleeps 10
Price per night from
$1,117
Location Location! St Michaels-- In Town Cottage!
St. Michaels house
- 2 bedrooms
- 2 bathrooms
- sleeps 5
Price per night from
$352
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.
Price per night from
$453
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.
Price per night from
$1,030
Responds fast! avg. 32 minutes
Price per night from
$257
Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!
Chester house
- 4 bedrooms
- 3 bathrooms
- sleeps 12
Price per night from
$458
Price per night from
$382
Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can
Stevensville house
- 4 bedrooms
- 2 bathrooms
- sleeps 12
Price per night from
$802
Price per night from
$229
KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12
Kent Island house
- 4 bedrooms
- 2 bathrooms
- sleeps 12
Price per night from
$1,947
DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12
Chester house
- 4 bedrooms
- 3 bathrooms
- sleeps 10
Price per night from
$1,947
Private setting, enjoy nature, kayaking and total relaxation
Bethlehem house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
Price per night from
$344
Price per night from
$1,890
Price per night from
$189
Price per night from
$682
Responds fast! avg. 38 minutes
Price per night from
$2,290
Luxury Waterfront - 40 Acre Estate - Swimming, Boating, Activities
Royal Oak manor house
- 25 bedrooms
- 25 bathrooms
- sleeps 50
Price per night from
$7,443
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
St. Michaels house
- 6 bedrooms
- 6 bathrooms
- sleeps 12
Responds fast! avg. 38 minutes
Price per night from
$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
Price per night from
$2,863
Price per night from
$1,260
Price per night from
$228
Beautiful Waterfront Home, Private Pool and Water Amenities- Sleeps 16
Cambridge house
- 5 bedrooms
- 3 bathrooms
- sleeps 18
Price per night from
$859
Private pier at Waterfront Kent Island home with Hot Tub (Open!)
Stevensville house
- 4 bedrooms
- 4 bathrooms
- sleeps 8
Price per night from
$456
Pool and Bay Views on wrap around deck in Kent Island
Stevensville house
- 3 bedrooms
- 3 bathrooms
- sleeps 12
Price per night from
$321
Price per night from
$429