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Talbot County Rentals

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Talbot County Rentals

67 Houses

Waterfront Room Rentals 2 with Private Beach

Trappe room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 34 minutes

Price per night from

$100

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Waterfront Room Rentals 3 with Private Beach

Trappe room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 34 minutes

Price per night from

$100

1 / 44

Waterfront Room Rentals 1 with Private Beach

Trappe room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 34 minutes

Price per night from

$131

1 / 34

Waterfront Vacation Home with Private Beach

Trappe house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 34 minutes

Price per night from

$332

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Halos'Haven Vacation Rental

McDaniel house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$703

1 / 15

Comfortable, Spacious & Fun! 6 Acres Pool & Shore

Wittman log cabin

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$980

1 / 36

St. Michaels Area Waterfront Retreat with pier, pool, kayaks and bikes

Royal Oak house

5 bedrooms / 4 bathrooms / sleeps 11

Price per night from

$602

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Pot Pie House

St. Michaels house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$226

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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

Price per night from

$201

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St. Michaels Waterfront Home W/Dock for 2 boats

Neavitt house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$226

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Historic Waterfront Property with Wi-Fi and Dock

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 21 minutes

Price per night from

$754

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St. Michaels Area Cottage - Walk to Water & Marina

Neavitt house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 30 minutes

Price per night from

$175

1 / 28

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$161

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Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 33 minutes

Price per night from

$377

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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 buildin

Price per night from

$152

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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

Price per night from

$161

1 / 23

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

Price per night from

$292

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Tranquil Easton Waterfront Property

Easton house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$603

1 / 15

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$150

1 / 24

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$246

1 / 6

Harris Cove Cottages LLC

St. Michaels cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$202

1 / 12

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

St. Michaels house

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$229

1 / 18

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

St. Michaels house

6 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$603

1 / 24

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.

Price per night from

$693

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Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$246

1 / 8

Halo's Haven Guest Quarters

St. Michaels house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$327

1 / 14

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

St. Michaels villa

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 1 hour 1 minutes

Price per night from

$850

1 / 38

Lakeside Private Apartment

Wye Mills apartment

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$139

1 / 15

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$388

1 / 9

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$287

1 / 7

RESTORED WATERFRONT COTTAGE

Royal Oak cottage

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$333

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