Updating...
Match: Non-Smoking property
All filters matchPrice per night from
$367
Private Waterview Estate with 4 bedroom Suites & Hot Tub
Shady Side house
- 6 bedrooms
- 7 bathrooms
- sleeps 14
Match: Non-Smoking property
All filters matchPrice per night from
$429
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
Match: Non-Smoking property
All filters matchPrice per night from
$716
“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.
Match: Non-Smoking property
All filters matchPrice per night from
$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.
Match: Non-Smoking property
All filters matchPrice per night from
$453
Match: Non-Smoking property
All filters matchPrice per night from
$344
Waterfront Property, Kayaks, Private Dock, Near Town
St. Michaels house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
Match: Non-Smoking property
All filters matchPrice per night from
$859
“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.
Match: Non-Smoking property
All filters matchPrice per night from
$458
Match: Non-Smoking property
All filters matchPrice per night from
$201
Match: Non-Smoking property
All filters matchPrice per night from
$201
KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12
Kent Island house
- 4 bedrooms
- 2 bathrooms
- sleeps 12
Match: Non-Smoking property
All filters matchPrice 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
Match: Non-Smoking property
All filters matchPrice per night from
$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
Match: Non-Smoking property
All filters matchPrice per night from
$802
Match: Non-Smoking property
All filters matchPrice per night from
$1,145
Match: Non-Smoking property
All filters matchPrice per night from
$229
Match: Non-Smoking property
All filters matchPrice per night from
$400
Responds fast! avg. 38 minutes
Match: Non-Smoking property
All filters matchPrice per night from
$2,290
Match: Non-Smoking property
All filters matchPrice per night from
$457
Match: Non-Smoking property
All filters matchPrice per night from
$401
Match: Non-Smoking property
All filters matchPrice per night from
$441
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
St. Michaels house
- 6 bedrooms
- 6 bathrooms
- sleeps 12
Responds fast! avg. 38 minutes
Match: Non-Smoking property
All filters matchPrice 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
Match: Non-Smoking property
All filters matchPrice per night from
$2,863
Match: Non-Smoking property
All filters matchPrice per night from
$367
Match: Non-Smoking property
All filters matchPrice per night from
$228
Match: Non-Smoking property
All filters matchPrice per night from
$630
Match: Non-Smoking property
All filters matchPrice per night from
$226
Match: Non-Smoking property
All filters matchPrice per night from
$343
Match: Non-Smoking property
All filters matchPrice per night from
$298
Match: Non-Smoking property
All filters matchPrice per night from
$572
Match: Non-Smoking property
All filters matchPrice per night from
$1,546
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis apartment
- 2 bedrooms
- 1 bathroom
- sleeps 6
Match: Non-Smoking property
All filters matchPrice per night from
$224
Match: Non-Smoking property
All filters matchPrice per night from
$315
Match: Non-Smoking property
All filters matchPrice per night from
$344
Match: Non-Smoking property
All filters matchPrice per night from
$682
Match: Non-Smoking property
All filters matchPrice per night from
$206
Match: Non-Smoking property
All filters matchPrice per night from
$458
Luxury Waterfront - 40 Acre Estate - Swimming, Boating, Activities
Royal Oak manor house
- 25 bedrooms
- 25 bathrooms
- sleeps 50
Match: Non-Smoking property
All filters matchPrice per night from
$7,443
Cozy Cool Spring waterfront apartment with pier mins to Annapolis
Arnold apartment
- 1 bedroom
- 1 bathroom
- sleeps 4
Match: Non-Smoking property
All filters matchPrice per night from
$177