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Houses Talbot County

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39 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.

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$719

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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$204

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

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$155

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 3 minutes

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$855

Tranquil Easton Waterfront Property

Easton house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 2 hours 31 minutes

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$6,870

St. Michaels Area Cottage - Walk to Water & Marina

Neavitt house

2 bedrooms / 2 bathrooms / sleeps 4

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$321

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

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$332

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

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$365

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

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$301

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 34 minutes

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$779

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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$523

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

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$439

Bay Cottage Resort

St. Michaels house

6 bedrooms / 5 bathrooms / sleeps 12

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$2,278

Great rentals within 20 miles that match your search

Clean & Spacious

Cape Saint Claire house

4 bedrooms / 5 bathrooms / sleeps 14

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$911

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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$342

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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$336

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

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

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$512

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

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

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$791

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

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$1,140

Responds fast! avg. 1 hour 4 minutes

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$456

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

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$285

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

Shady Side house

3 bedrooms / 2 bathrooms / sleeps 6

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$377

Annapolis Home w/ Deck & Whitehall Bay Access

Cape Saint Claire house

4 bedrooms / 2 bathrooms / sleeps 8

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$234

Waterfront Annapolis Home: Fire Pit & Fishing Pier

Cape Saint Claire house

3 bedrooms / 1 bathroom / sleeps 6

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$275

Private setting, enjoy nature, kayaking and total relaxation

Bethlehem house

3 bedrooms / 2 bathrooms / sleeps 8

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$228

Annapolis House w/ Patio in Bay Ridge Maryland!

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

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$663

Charming Annapolis Waterview home

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

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$801

Walkable to Downtown Annapolis

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 25 minutes

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$438

New! Steps from the Waterfront in Eastport

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 25 minutes

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$377

New-Kent Island House with Pool and Bay Views!

Stevensville house

3 bedrooms / 3 bathrooms / sleeps 13

Responds fast! avg. 1 hour 25 minutes

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$381

Renovated Eastport Firehouse in Annapolis

Annapolis house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 25 minutes

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$492

New Luxury Home Walkable to Main Street w Parking!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 25 minutes

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$182

Naval Academy Themed at the Gates with parking!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 11

Responds fast! avg. 1 hour 25 minutes

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$524

Newly Managed Randall House in Downtown Annapolis

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 11

Responds fast! avg. 1 hour 25 minutes

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$410

New - Gorgeous downtown Annapolis home with parking for days!

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 1 hour 25 minutes

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$381

Historic Charm! Walk to Annapolis Waterfront & Academy

Annapolis house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 25 minutes

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$588

Water Views from Every Window!

Edgewater house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 25 minutes

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Price per night from

$369

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