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Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Jacuzzi or hot tub
Garden
Internet access
DVD player
Grill
Fireplace
Cot available
Sea view
Safe
Dishwasher
Satellite TV
Children's pool
Clothes dryer
Games room
Shared indoor pool
Private outdoor pool (unheated)
Private outdoor pool (heated)
Pool or snooker table
Shared outdoor pool (unheated)
Shared outdoor pool (heated)
Cribs
Ceiling Fans
Table tennis
Private fishing lake or river
Fax machine
Freezer
Stereo system
Kettle
Toaster
Iron
Hair dryer
Stove
Fridge
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Video player
Linen provided
Towels provided
Bicycles available
Climbing frame
Swing set or jungle gym
Trampoline
Staffed property
Boat available
Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Elevator access
Wheelchair adapted
Wheelchair accessible
Secure parking

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Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
Nightlife
Water sports
Horse riding
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Cycling trips
Golf course on site or within 15 min walk
Waterfront
Beach or lakeside relaxation
Golf within 30mins drive
Lakefront

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127 Houses

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180-degree water views at unique round house

Shady Side house

3 bedrooms
2 bathrooms

sleeps 8

Price per night from

$367

Private Waterview Estate with 4 bedroom Suites & Hot Tub

Shady Side house

6 bedrooms
7 bathrooms

sleeps 14

Price 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

Price per night from

$716

Perfect Annapolis with Lots of Parking & Hot Tub

Annapolis townhouse

4 bedrooms
3 bathrooms

sleeps 10

Price per night from

$796

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms
2 bathrooms

sleeps 5

Price per night from

$352

Beautiful Murray Hill Home (Annapolis)

Annapolis house

4 bedrooms
3 bathrooms

sleeps 9

“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

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

2. Private 20 acre waterfront estate - studio apt

Annapolis apartment

1 bedroom
1 bathroom

sleeps 2

Price per night from

$344

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

Love Point Waterfront

Kent Island house

3 bedrooms
3 bathrooms

sleeps 12

“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.

Price per night from

$458