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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 35 minutes

Price per night from

$100

1 / 42

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$244

1 / 8

Halos'Haven Vacation Rental

McDaniel house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$700

1 / 15

Waterfront Room Rentals 1 with Private Beach

Trappe room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 35 minutes

Price per night from

$130

1 / 34

Waterfront Room Rentals 3 with Private Beach

Trappe room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 35 minutes

Price per night from

$100

1 / 44

St. Michaels Waterfront Home W/Dock for 2 boats

Neavitt house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$225

1 / 18

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

Price per night from

$374

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Main House at Grandview at Pleasure Point

Bozman house

5 bedrooms / 3 bathrooms / sleeps 13

“Scenic, peaceful, nature's treat!” 10 yrs ago we stayed for a few days at a Grandview cottage while exploring the Eastern Shore. We've been back every yr bringing family & friends,now enjoying the entire estate.Love crabbing,fishing,boating &relaxing; in the pool.My favorite place is the dock: watching waterman, birds, fish, the sun go down as the moon comes up. Heaven!

Price per night from

$688

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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

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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 10 minutes

Price per night from

$747

1 / 18

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$244

1 / 6

Tranquil Easton Waterfront Property

Easton house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$600

1 / 15

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 they also enjoyed checking out the boats in the marina right across the street and watching the working drawbridge (within walking distance). It was great for young kids, but would also be perfect for couples or a group of adults looking for a pleasant visit to the Eastern Shore. We were not ready to leave and will make plans to go back! Tilghman Island is quiet and a little off the beaten path compared to some of the larger towns, which makes for a relaxing escape from the city. It offers an "authentic" Eastern Shore experience in a community of working watermen, but at the same time it is only a 10 minute drive from the shops of St. Michaels. On Tilghman Island, we had an excellent seafood supper at Mike & Eric's and a really good breakfast at Two If By Sea. We also visited during the Waterfowl Festival in Easton, which was a really good time. The owners are pleasant and very easy to deal with. We highly recommend staying at this cottage!

Price per night from

$200

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Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$151

1 / 27

Comfortable, Spacious & Fun! 6 Acres Pool & Shore

Wittman log cabin

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$975

1 / 36

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

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

Royal Oak house

5 bedrooms / 4 bathrooms / sleeps 11

Price per night from

$597

1 / 4

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$160

1 / 25

Waterfront Vacation Home with Private Beach

Trappe house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 35 minutes

Price per night from

$329

1 / 55

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

St. Michaels house

6 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$598

1 / 24

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$385

1 / 9

Harris Cove Cottages LLC

St. Michaels cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$200

1 / 12

Pot Pie House

St. Michaels house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$226

1 / 12

St. Michaels Area Cottage - Walk to Water & Marina

Neavitt house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 16 minutes

Price per night from

$175

1 / 28

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

$851

1 / 38

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

St. Michaels house

7 bedrooms / 4 bathrooms / sleeps 9

“This was the perfect home for a week of wedding planning and family relaxation time.” Our daughter was married at the Tidewater Inn in Easton. We rented this lovely, large home the week before the wedding to have a place for the bride to relax while we spent time together finalizing wedding plans. The stay at the Harrison Home added so many memories to the already fond memories of a wedding. We cooked together with all the amenities in the kitchen. The home was so large we could gather around the 2 large tables for dinner, everyone had their own rooms, we had plenty of hot water, towels, cards, movies, kayaks. Everyone was pleased with the many comforts of home. Some highlights were simply all the space. The bride had her own quarters. All the wedding decorations were in a den which led to her private bedroom and bath. We spent time grilling outside and sitting on the porch singing old camp songs. The home is located right on the harbor allowing the young adults to go for appetizers and drinks at the local venues. We loved the shopping a block away. So many memories! Tom was great to work with and made sure we had everything we needed. I wish we could do this all over again! I would not change a thing.

Price per night from

$289

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Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$150

1 / 24

Halo's Haven Guest Quarters

St. Michaels house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$324

1 / 14

Lakeside Private Apartment

Wye Mills apartment

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$139

1 / 15

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$285

1 / 7

RESTORED WATERFRONT COTTAGE

Royal Oak cottage

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$329

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