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Houses Annapolis

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46 houses

Annapolis Area Waterfront Home

Annapolis house

5 bedrooms / 4 bathrooms / sleeps 11

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$557

Excellent Location in Downtown Annapolis- walk to everything !

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 3 hours 28 minutes

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Price per night from

$327

Charming and Spacious Annapolis Victorian

Annapolis house

6 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 22 minutes

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$860

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

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$287

Annapolis House w/ Patio in Bay Ridge Maryland!

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 27 minutes

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$666

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.

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$487

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

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$795

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

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$1,228

Cozy Home in Historic Annapolis with Parking

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 14 minutes

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$228

Charming Annapolis Waterview home

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

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$801

Charming Annapolis Home w/ Yard - 5 Mins to Dwtn!

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 27 minutes

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$303

Charming Townhouse - Steps to City Dock and USNA

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

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$553

Great rentals within 20 miles that match your search

Panoramic Views of Herrington Harbour on the Bay.

North Beach house

3 bedrooms / 2 bathrooms / sleeps 8

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$613

Wellspring Manor & Spa

Largo house

5 bedrooms / 8 bathrooms / sleeps 10

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$2,007

Lochhaven house for rent

Edgewater house

3 bedrooms / 1 bathroom / sleeps 2

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$123

Private Room Close To Baltimore and BWI Airport + EXTRAS

Glen Burnie house

1 bedroom / 1 bathroom / sleeps 2

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$56

Simply Severn - Comfortable and Close to Everything in the DC Area.

Severn house

3 bedrooms / 3 bathrooms / sleeps 8

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$215

Holistic Getaway

Bowie house

2 bedrooms / 1 bathroom / sleeps 6

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$178

KENT ISLAND-OCEAN VIEW Home for rent -4 bedrooms EASTERN SHORE sleeps 10-12

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 17 minutes

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$1,596

Clean & Spacious

Cape Saint Claire house

4 bedrooms / 5 bathrooms / sleeps 14

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$965

Bay Cottage

Rock Hall house

2 bedrooms / 1 bathroom / sleeps 5

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$328

Sailors Crossing

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 10

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$430

Waterfront Annapolis Area 3BR/3BA Retreat with Private Pier

Edgewater house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 24 minutes

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$483

Bayside Retreat

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 6

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$332

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.

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$289

Huge Stevensville Home w/Pool & Eastern Shore View

Stevensville house

3 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 20 minutes

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Price per night from

$475

Bay Cottage Resort

St. Michaels house

6 bedrooms / 5 bathrooms / sleeps 14

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$2,304

KI Golf House-A PAR for the Course & Mile to Beach

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

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$462

Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina

Stevensville house

4 bedrooms / 2 bathrooms / sleeps 12

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$467

Responds fast! avg. 29 minutes

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$401

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

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$441

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 32 minutes

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$401

'Serenity in Severn' Home w/ Yard & Seasonal Pool

Severn house

4 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 43 minutes

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$266

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.

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$327

Annapolis Area Shagrila Resort

Davidsonville house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 26 minutes

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$459

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

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$281

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

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$235

Large Historic Thomas Harrison House on Harbor in St. Michaels Town

St. Michaels house

7 bedrooms / 4 bathrooms / sleeps 9

“Perfect in every way!” I stayed at the Thomas Harrison house a few weeks ago and all I can say is..."if you are planning on coming to St. Michael's you need to stay at this house." This house is perfect in every way. It has all the accommodations that you could ever need and is very unique and quaint. The location is more than perfect (we literally were in walking distance of everything, shops, restaurants, etc.) and did not even have to get into the car to drive anywhere the entire time. The backyard has a wonderful porch where you can sit outside and converse with friends or even sip your coffee in the morning. The view is phenomenal! You have a wonderful panoramic view of the water from your bedroom window and the beds are very comfortable (which is a must for me). If you are planning on a trip to experience St. Michael's whether it is a romantic weekend getaway or a family (group) outing I would hands down recommend this house.

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$447

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