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Claiborne Rentals

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Claiborne Rentals

31 Houses

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / Sleeps 5

$150

1 / 24

Tilghman Island Cottage for Six - Near Marina and Knapps Narrows Drawbridge

Tilghman cottage

3 bedrooms / 2 bathrooms / Sleeps 6

“We loved it!” We had a great (albeit too short!) family getaway at the Roost! The cottage is extremely clean, comfortable, well-maintained, and spacious. The kids (ages 6 and 20 months) loved it -- especially the bunk beds and the nice backyard, and t

$200

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Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

St. Michaels cottage

2 bedrooms / 2 bathrooms / Sleeps 5

$159

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Charming Coastal Cottage Minutes to St. Michaels

Wittman house

2 bedrooms / 2 bathrooms / Sleeps 6

$175

1 / 8

Halos'Haven Vacation Rental

McDaniel house

5 bedrooms / 3 bathrooms / Sleeps 10

$700

1 / 15

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / Sleeps 5

“Stepping back in history with today's amenities” This cottage was very nicely restored to capture the historic feel of colonial times, yet equipped with the modern conveniences. Since we visited during the winter, we especially enjoyed the fireplace.

$149

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

St. Michaels house

7 bedrooms / 4 bathrooms / Sleeps 9

“Comfortable, large home with perfect location!” My daughter was married in St. Michaels in May so I rented this house and filled it with family. It was a perfect "home base" for all of the activities surrounding the wedding, walking distance to all of

$290

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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,

$179

1 / 21

Historic Waterfront Property with Wi-Fi and Dock

St. Michaels house

3 bedrooms / 3 bathrooms / Sleeps 8

$750

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Tranquil Easton Waterfront Property

Easton house

3 bedrooms / 3 bathrooms / Sleeps 6

$600

1 / 15

Comfortable, Spacious & Fun! 6 Acres Pool & Shore

St. Michaels log cabin

5 bedrooms / 5 bathrooms / Sleeps 10

$975

1 / 35

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / Sleeps 10

“Perfect weekend getaway!” My family recently spent a memorable weekend in December at Sandy Pines. We comfortably shared the house with a group of friends -- three other couples and their young children. The house has a lovely home-away-from-home feel

$373

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New! Waterfront 5BR Stevensville House w/ Pier!

Stevensville house

5 bedrooms / 2 bathrooms / Sleeps 12

$375

1 / 25

NEW! 2BR St. Michaels Area Cottage- Walk to Marina

Neavitt house

2 bedrooms / 2 bathrooms / Sleeps 4

$175

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Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / Sleeps 2

$188

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Main House at Grandview at Pleasure Point

Bozman house

5 bedrooms / 3 bathrooms / Sleeps 13

“Great place for our business retreat” This house was the perfect size for our staff of 8 for our annual staff retreat. The rooms were comfortable. The size of the dining room table was great for our meetings. We enjoyed quiet time sitting on the do

$564

1 / 34

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / Sleeps 6

“Wonderful!” Our family has been vacationing at Grandview for over 20 years. I think that says it all. Beautiful location, gorgeous sunsets, peaceful and quite. Serene. Plenty of crabbing, swimming, fishing and just plan relaxing. The cottages are

$295

1 / 9

Harris Cove Cottages LLC

St. Michaels cottage

1 bedroom / 1 bathroom / Sleeps 4

$164

1 / 12

Serene Waterfront Apartment on Kent Island

Stevensville apartment

1 bedroom / 1 bathroom / Sleeps 2

$130

1 / 12

St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds

St. Michaels villa

6 bedrooms / 6 bathrooms / Sleeps 12

$850

1 / 38

Halo's Haven Guest Quarters

St. Michaels house

3 bedrooms / 2 bathrooms / Sleeps 6

$325

1 / 14

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

St. Michaels house

1 bedroom / 1 bathroom / Sleeps 6

$229

1 / 18

Best sunrise in St. Michaels....Broadview Bay House

St. Michaels house

6 bedrooms / 3 bathrooms / Sleeps 12

$600

1 / 24

3BR Stevensville House Overlooking Eastern Shore!

Stevensville house

3 bedrooms / 5 bathrooms / Sleeps 8

$400

1 / 26

St. Michaels Waterfront Home W/Dock for 2 boats

Neavitt house

2 bedrooms / 1 bathroom / Sleeps 5

$250

1 / 18

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / Sleeps 4

$283

1 / 7

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / Sleeps 4

$187

1 / 8

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / Sleeps 5

$159

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RESTORED WATERFRONT COTTAGE

Royal Oak cottage

3 bedrooms / 3 bathrooms / Sleeps 6

$280

1 / 24

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

Kent Island house

4 bedrooms / 3 bathrooms / Sleeps 10

$425

1 / 17

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

Stevensville house

4 bedrooms / 2 bathrooms / Sleeps 12

$450

1 / 9
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