Houses St. Michaels

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49 houses

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.

Responds fast! avg. 3 hours 23 minutes

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$447

Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX

St. Michaels house

1 bedroom / 1 bathroom / sleeps 6

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$264

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

“Crabtastic Great Escape” This cottage is the perfect great escape. Conveniently located in the middle of quaint St Michael's close to the harbor, restaurants, and shops. The property is clean and well-maintained with beautiful landscaping. The building has been lovingly restored keeping to the historical accuracy, yet well placed modern conveniences make the stay even more enjoyable. I have visited this cottage several times and will continue to do so! A great place to gather with family and friends or a quick weekend escape to enjoy life on the shore.

Responds fast! avg. 3 hours 23 minutes

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$225

Pot Pie House

St. Michaels house

3 bedrooms / 2 bathrooms / sleeps 6

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$259

Historic Waterfront Property with Wi-Fi and Dock

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 22 minutes

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$863

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 23 minutes

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$236

Halo's Haven Guest Quarters

St. Michaels house

3 bedrooms / 2 bathrooms / sleeps 6

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$374

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 10

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$576

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

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$441

Great rentals within 20 miles that match your search

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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$294

Charming Artists Home in Eastport/Annapolis

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

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$437

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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$495

Panoramic Views of Herrington Harbour on the Bay.

North Beach house

3 bedrooms / 2 bathrooms / sleeps 8

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$578

Renovated Luxury Waterview House

North Beach house

3 bedrooms / 2 bathrooms / sleeps 6

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$347

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

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$803

Charming Townhouse - Steps to City Dock and USNA

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

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$518

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. 59 minutes

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$1,735

Private setting, enjoy nature, kayaking and total relaxation

Bethlehem house

3 bedrooms / 2 bathrooms / sleeps 8

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$230

Modern Luxury Rental in North Beach!

North Beach house

1 bedroom / 1 bathroom / sleeps 4

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$127

Indoor pool and spa located in beautiful Southern Maryland woodlands

Chesapeake Beach house

3 bedrooms / 3 bathrooms / sleeps 8

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$576

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

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

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$461

EASTERN SHORE MARYLAND WELCOMES YOU

Preston house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 15 minutes

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$87

Tranquil Easton Waterfront Property

Easton house

3 bedrooms / 3 bathrooms / sleeps 6

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$691

Main House at Grandview at Pleasure Point

Bozman house

5 bedrooms / 3 bathrooms / sleeps 13

“5 out of 5” I spent a long weekend at the main house, and it was easily the best weekend of the summer! The location is phenomenal. The house sits on large stretch of beautiful waterfront property. The views from the piers and the pool are exquisite. As for the house itself, we couldn't have asked for more. It is spacious, clean, and has all of the amenities you could want. I must also mention that it was a breeze and a pleasure working with the folks at Grandview. They are incredibly responsive, and make a great effort to ensure that you enjoy your stay.

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$654

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

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$340

Charming Annapolis home with stunning water views

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 11

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$576

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

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$1,151

Love Point Luxury Waterfront in Stevensville

Stevensville house

3 bedrooms / 4 bathrooms / sleeps 10

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$1,610

Excellent Location in Downtown Annapolis- walk to everything !

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 41 minutes

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$328

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$403

Your Eastport Annapolis Haven!

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 16 minutes

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$486

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 27 minutes

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$288

Charming Eastport Home

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 8

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$345

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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$484

Annapolis House w/ Patio in Bay Ridge Maryland!

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 1 hour 10 minutes

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$719

NEW! Waterfront Home Near Annapolis

Mayo house

4 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 1 hour 10 minutes

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$547

St. Michaels Waterfront Retreat with pier, pool, kayaks, gas fire pit and bikes

Royal Oak house

5 bedrooms / 4 bathrooms / sleeps 10

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$574

Cambridge Colonial Home, Walk to Town & Waterfront

Cambridge house

3 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 1 hour 10 minutes

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Price per night from

$276

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