Updating...
Match: Non-Smoking property
All filters matchPrice per night from
$276
Match: Non-Smoking property
All filters matchPrice per night from
$228
Great rentals within 20 miles that match your search
“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
$488
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
“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
$459
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
$1,950
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
$1,950
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
$803
Match: Non-Smoking property
All filters matchPrice per night from
$1,147
Match: Non-Smoking property
All filters matchPrice per night from
$58
Match: Non-Smoking property
All filters matchPrice per night from
$402
Match: Non-Smoking property
All filters matchPrice per night from
$401
Match: Non-Smoking property
All filters matchPrice per night from
$442
Match: Non-Smoking property
All filters matchPrice per night from
$367
Match: Non-Smoking property
All filters matchPrice per night from
$229
Match: Non-Smoking property
All filters matchPrice per night from
$573
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
$683
Match: Non-Smoking property
All filters matchPrice per night from
$207
Match: Non-Smoking property
All filters matchPrice per night from
$918
Match: Non-Smoking property
All filters matchPrice per night from
$459
Waterfront| 4BR| 1st Floor Master|Family Ready|Bwi
Glen Burnie house
- 4 bedrooms
- 3 bathrooms
- sleeps 8
Match: Non-Smoking property
All filters matchPrice per night from
$305
Steps to Gate 1 and Free Parking at Naval-Academy Themed Home
Annapolis house
- 4 bedrooms
- 2 bathrooms
- sleeps 11
Match: Non-Smoking property
All filters matchPrice per night from
$610
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
Family Times in river community mins to Annapolis, Pet-friendly
Arnold house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
Match: Non-Smoking property
All filters matchPrice per night from
$251
Waterfront family resort Lodge with private pier, game room and bar
Centreville house
- 5 bedrooms
- 4 bathrooms
- sleeps 15
Match: Non-Smoking property
All filters matchPrice per night from
$400
Still Available for 2024 Commissioning Week! Historic gem steps to USNA
Annapolis house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
Match: Non-Smoking property
All filters matchPrice per night from
$465
Hanover House across from USNA Gate 3 with private back patio
Annapolis house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
Match: Non-Smoking property
All filters matchPrice per night from
$465
Match: Non-Smoking property
All filters matchPrice per night from
$518
New Luxury Lighthouse Inn with parking, private backyard, walkable to downtown
Annapolis house
- 4 bedrooms
- 4 bathrooms
- sleeps 12
Match: Non-Smoking property
All filters matchPrice per night from
$500
Private pier and pool at this waterfront Chestertown home
Chestertown house
- 5 bedrooms
- 4 bathrooms
- sleeps 14
Match: Non-Smoking property
All filters matchPrice per night from
$413
Match: Non-Smoking property
All filters matchPrice per night from
$204
Parking at Stunning On Cloud 9 with private patio pet-friendly
Annapolis house
- 4 bedrooms
- 4 bathrooms
- sleeps 10
Match: Non-Smoking property
All filters matchPrice per night from
$500
Pool and Bay Views on wrap around deck in Kent Island
Stevensville house
- 3 bedrooms
- 3 bathrooms
- sleeps 12
Match: Non-Smoking property
All filters matchPrice per night from
$321
Ahoy! The Buccaneer awaits you just outside Annapolis - fenced-in yard and rec r
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 9
Match: Non-Smoking property
All filters matchPrice per night from
$355
Free Parking with private fenced-in backyard with pool table at Weekender
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Match: Non-Smoking property
All filters matchPrice per night from
$292
Stunning waterfront home with deep water private pier minutes to Annapolis
Crownsville house
- 4 bedrooms
- 4 bathrooms
- sleeps 12
Match: Non-Smoking property
All filters matchPrice per night from
$561
Historic happy home, steps to Main Street, parking and lots of outdoor space
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
Match: Non-Smoking property
All filters matchPrice per night from
$465