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Indoor pool and spa located in beautiful Southern Maryland woodlands
Chesapeake Beach house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
Price per night from
$1,105
Price per night from
$226
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
“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.
Price per night from
$487
Vintage Bungalow-cozy, walk to shops, water, free pkg.
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$476
Waterfront Property, Kayaks, Private Dock, Near Town
St. Michaels house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
Price per night from
$859
Price per night from
$201
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
$400
Price per night from
$441
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
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
Price per night from
$149
Responds fast! avg. 38 minutes
Price per night from
$2,290
Price per night from
$630
Beautiful Waterfront Home, Private Pool and Water Amenities- Sleeps 16
Cambridge house
- 5 bedrooms
- 3 bathrooms
- sleeps 18
Price per night from
$859
Price per night from
$343
Price per night from
$298
Price per night from
$572
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis apartment
- 2 bedrooms
- 1 bathroom
- sleeps 6
Price per night from
$224
Price per night from
$315
Price per night from
$1,890
Blue Pearl - Life on the River! Luxury estate with jacuzzi and private pier!
Broomes Island house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
Price per night from
$400
Luxury Waterfront home with private pier and guest house
Annapolis house
- 5 bedrooms
- 4 bathrooms
- sleeps 12
Price per night from
$907
Walk to Main Street from Waterfront Condo with pool and parking
Annapolis condo
- 2 bedrooms
- 2 bathrooms
- sleeps 7
Price per night from
$407
Price per night from
$367
Cottage by the Bay on one level in family-friendly community
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
Price per night from
$367
Eastport Bungalow - Popular house Walk to Downtown & USNA
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 7
Price per night from
$400
Private Waterfront Retreat with Pool, Hot Tub and Game Room
Tracys Landing house
- 5 bedrooms
- 4 bathrooms
- sleeps 14
Price per night from
$727
Waterfront pier, putting green just minutes from downtown Annapolis
Riva house
- 4 bedrooms
- 4 bathrooms
- sleeps 10
Price per night from
$725
Eastport Gem - Popular house walk to Downtown & USNA
Annapolis house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
Price per night from
$400
Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the
Annapolis cottage
- 3 bedrooms
- 2 bathrooms
- sleeps 8
Price per night from
$407