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Tilghman Estates

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50 rentals in Tilghman.
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Fully remodel 2 bedroom country cottage.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Simplicity Cottage - Renovated Waterman's Home Circa 1920, Relax in the Hammock!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Relax in Tilghman Island

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
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Time to book your 2020 Sunset vacation!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Tilghman Island Cottage - Across from Marina and Knapps Narrows

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Looking to get away this September? Gorgeous waterfront property awaits.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Not to early to think about joining us this Spring and Summer.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Clearview - Tilghman Island Cottage, Big Amenities: Pool, Hot Tub, Amazing Views

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Rental Home
7 bedrooms
9 bathrooms
Sleeps 12
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BREATHTAKING WATERFRONT ESTATE

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
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Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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Comfy home on beautiful Leadenham Creek. Book now for summer!

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town

Rental Home
5 bedrooms
4 bathrooms
Sleeps 8
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Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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Perfect Waterview Cottage - St. Michaels Getaway

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Comfortable Relaxing Spacious & Fun! 6+ Acres Pool+Bay Waterfront by St Michaels

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
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Walk to Everything House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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BEAUTIFUL WATERFRONT HOME AVAILABLE NOW!!!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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St. Michaels Area Cottage - Walk to Water & Marina

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Holidays at the Cove - plenty of space to gather while making memories

Rental Home
5 bedrooms
7 bathrooms
Sleeps 10
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Cottage downtown on a quiet street

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
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New Modern Waterfront Farmhouse Built 2018

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Waterfront Home with Magnificent Views

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
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Secluded Waterfront Property on 3 acres with swimming pool and dock.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Eastern Shore Getaway Near St. Michaels

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
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Caulk's Cove - Waterfront Near St. Michaels, Bikes, Kayaks!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
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Location Location! St Michaels-- In Town Cottage!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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*****Waterfront home w/ pool in St. Michaels

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Large waterfront estate with breathtaking sunset views

Rental Home
8 bedrooms
5 bathrooms
Sleeps 12
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Premier Cottage in St. Michaels- In Town Location!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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Main House at Grandview at Pleasure Point

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
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Luxury Waterfront with pool and deep water dock, minutes from St Michaels.

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Mallard Point Cottage - Relaxing Waterfront Home, Kayaks, Bikes, Pet-Friendly!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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CHESAPEAKE MANSION - HEATED POOL/ 12,000 SQFT/ 30 ACRES

Rental Home
8 bedrooms
10 bathrooms
Sleeps 12
Match: Sleeps
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Sandy Pines: Enjoy Harris Creek w/Pool and Boats

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterview Cottage In St. Michaels!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Emily's Lane - Quaint Waterfront Near St. Michaels - Pool, Grill, Game Room!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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The Water House - Unique 3600-SqFt Home Near St. Michaels, Pets Welcome!

Rental Home
5 bedrooms
6 bathrooms
Sleeps 9
Match: Sleeps
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The Landing - Peaceful Waterfront Home, BBQ, Kayak & Fire Pit!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Carpenter Alley - Newly-Renovated, Pet-Friendly - Heart of Charming St. Michaels

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cottage 2 at Grandview Pleasure Point

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Cabin
5 bedrooms
5 bathrooms
Sleeps 10
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Cottage 1a at Grandview Pleasure Point

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cottage 1b at Grandview Pleasure Point

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming St Michaels Home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Waterfront Estate w/Pool, Dock, Sunset views near St. Michaels, sleeps 12+

Rental Home
7 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Pines at Barrett Cove - Exquisitely Renovated, Pool, Hot Tub, Outdoor Kitchen!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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