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Talbot County Rentals

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Talbot County Rentals

70 house rentals

$217

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

St. Michaels cottage

2 bedrooms / 2 bathrooms / sleeps 5

$217

1 / 23

$200

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

1 / 20

$101

Waterfront Room Rentals 2 with Private Beach

Trappe room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 38 minutes

$101

1 / 42

$386

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

$386

1 / 9

$600

Tranquil Easton Waterfront Property

Easton house

3 bedrooms / 3 bathrooms / sleeps 6

$600

1 / 15

$330

Waterfront Vacation Home with Private Beach

Trappe house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 38 minutes

$330

1 / 55

$377

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 48 minutes

$377

1 / 22

$700

Halos'Haven Vacation Rental

McDaniel house

5 bedrooms / 3 bathrooms / sleeps 10

$700

1 / 15

$245

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

$245

1 / 6

$229

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

$690

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.

$690

1 / 34

$195

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

$195

1 / 27

$750

Historic Waterfront Property with Wi-Fi and Dock

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 34 minutes

$750

1 / 18

$390

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

$390

1 / 30

$225

Pot Pie House

St. Michaels house

3 bedrooms / 2 bathrooms / sleeps 6

$225

1 / 12

$599

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

Royal Oak house

5 bedrooms / 4 bathrooms / sleeps 11

$599

1 / 4

$205

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

$205

1 / 24

$250

St. Michaels Waterfront Home W/Dock for 2 boats

Neavitt house

2 bedrooms / 1 bathroom / sleeps 5

$250

1 / 18

$175

St. Michaels Area Cottage - Walk to Water & Marina

Neavitt house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 32 minutes

$175

1 / 28

$130

Waterfront Room Rentals 1 with Private Beach

Trappe room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 38 minutes

$130

1 / 34

$101

Waterfront Room Rentals 3 with Private Beach

Trappe room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 38 minutes

$101

1 / 44

$650

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

St. Michaels house

6 bedrooms / 3 bathrooms / sleeps 12

$650

1 / 24

$975

Comfortable, Spacious & Fun! 6 Acres Pool & Shore

Wittman log cabin

5 bedrooms / 5 bathrooms / sleeps 10

$975

1 / 36

$855

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

$855

1 / 38

$200

Harris Cove Cottages LLC

St. Michaels cottage

1 bedroom / 1 bathroom / sleeps 4

$200

1 / 12

$245

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

$245

1 / 8

$324

Halo's Haven Guest Quarters

St. Michaels house

3 bedrooms / 2 bathrooms / sleeps 6

$324

1 / 14

$215

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

$215

1 / 25

$285

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

$285

1 / 7

$139

Lakeside Private Apartment

Wye Mills apartment

1 bedroom / 1 bathroom / sleeps 5

$139

1 / 15

$330

RESTORED WATERFRONT COTTAGE

Royal Oak cottage

3 bedrooms / 3 bathrooms / sleeps 6

$330

1 / 24
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