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Tilghman Holiday Rentals

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50 rentals in Tilghman.
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Fully remodel 2 bedroom country cottage., holiday rental in Tilghman

Fully remodel 2 bedroom country cottage.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Relax in Tilghman Island, holiday rental in Tilghman

Relax in Tilghman Island

4 bedrooms
2 bathrooms
Sleeps 6
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Not to early to think about joining us this Spring and Summer., holiday rental in Tilghman

Not to early to think about joining us this Spring and Summer.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS), holiday rental in Tilghman

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

7 bedrooms
9 bathrooms
Sleeps 20
Match: Sleeps
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Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway, holiday rental in Tilghman

Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Play & relax at the Bungalow! Easily walk to beautiful Herrington Harbour South!, holiday rental in Tilghman

Play & relax at the Bungalow! Easily walk to beautiful Herrington Harbour South!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!, holiday rental in Tilghman

TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Comfy home on beautiful Leadenham Creek. Book now for summer!, holiday rental in Tilghman

Comfy home on beautiful Leadenham Creek. Book now for summer!

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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St. Michael's Waterfront Vacation Home, holiday rental in Tilghman

St. Michael's Waterfront Vacation Home

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Spacious house with great deck close to boardwalk, shops, and restaurants., holiday rental in Tilghman

Spacious house with great deck close to boardwalk, shops, and restaurants.

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Chesapeake Bay Cottage, holiday rental in Tilghman

Chesapeake Bay Cottage

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming 3 Bedroom 3 Bath Beach Front Property, holiday rental in Tilghman

Charming 3 Bedroom 3 Bath Beach Front Property

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Waterfront Family Retreat with Deepwater Dock, holiday rental in Tilghman

Waterfront Family Retreat with Deepwater Dock

4 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Beautiful Tidewater home between Easton & ST Michaels!, holiday rental in Tilghman

Beautiful Tidewater home between Easton & ST Michaels!

4 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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Escape To This Oxford, Md Waterfront Home - Kayaking, Canoeing & Relaxing, holiday rental in Tilghman

Escape To This Oxford, Md Waterfront Home - Kayaking, Canoeing & Relaxing

4 bedrooms
5 bathrooms
Sleeps 8
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Stunning Cottage Newly Renovated 2 Bed 2 Bath Sleeps 6 with an AMAZING Yard, holiday rental in Tilghman

Stunning Cottage Newly Renovated 2 Bed 2 Bath Sleeps 6 with an AMAZING Yard

2 bedrooms
2 bathrooms
Sleeps 6
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Lovely 3 bedroom 2 bath fully renovated cottage Sleeps 6, holiday rental in Tilghman

Lovely 3 bedroom 2 bath fully renovated cottage Sleeps 6

3 bedrooms
2 bathrooms
Sleeps 6
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Holidays at the Cove  - plenty of space to gather while making memories, holiday rental in Tilghman

Holidays at the Cove - plenty of space to gather while making memories

5 bedrooms
7 bathrooms
Sleeps 10
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Waterfront, Water All Around, Peaceful Family Getaway, holiday rental in Tilghman

Waterfront, Water All Around, Peaceful Family Getaway

3 bedrooms
2 bathrooms
Sleeps 6
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Unbelievable Home Newly Renovated Sleeps Up to 9, holiday rental in Tilghman

Unbelievable Home Newly Renovated Sleeps Up to 9

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton, holiday rental in Tilghman

Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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New Modern Waterfront Farmhouse Built 2018, holiday rental in Tilghman

New Modern Waterfront Farmhouse Built 2018

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Eastern Shore Getaway Near St. Michaels, holiday rental in Tilghman

Eastern Shore Getaway Near St. Michaels

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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407 Southwinds - Renovated with Direct Chesapeake Bay View near DC and Annapolis, holiday rental in Tilghman

407 Southwinds - Renovated with Direct Chesapeake Bay View near DC and Annapolis

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront Getaway on the Choptank River, holiday rental in Tilghman

Waterfront Getaway on the Choptank River

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Bayfront Home with Amazing Rooftop Deck!, holiday rental in Tilghman

Bayfront Home with Amazing Rooftop Deck!

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Location Location! St Michaels-- In Town Cottage!, holiday rental in Tilghman

Location Location! St Michaels-- In Town Cottage!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Sweet Spot Cottage on the Bay, holiday rental in Tilghman

Sweet Spot Cottage on the Bay

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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*****Waterfront home w/ pool in St. Michaels, holiday rental in Tilghman

*****Waterfront home w/ pool in St. Michaels

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Premier Cottage in St. Michaels- In Town Location!, holiday rental in Tilghman

Premier Cottage in St. Michaels- In Town Location!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Crystal Cove Retreat, holiday rental in Tilghman

Crystal Cove Retreat

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Holiday on the Bay, Kent Island Beach House, holiday rental in Tilghman

Holiday on the Bay, Kent Island Beach House

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Main House at Grandview at Pleasure Point, holiday rental in Tilghman

Main House at Grandview at Pleasure Point

5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Large Historic Thomas Harrison House on Harbor in St. Michaels Town, holiday rental in Tilghman

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

7 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa, holiday rental in Tilghman

BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!, holiday rental in Tilghman

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

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Sandy Pines:  Enjoy Harris Creek w/Pool and Boats, holiday rental in Tilghman

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterview Cottage In St. Michaels!, holiday rental in Tilghman

Waterview Cottage In St. Michaels!

2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX, holiday rental in Tilghman

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

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview, holiday rental in Tilghman

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Cottage 2 at Grandview Pleasure Point, holiday rental in Tilghman

Cottage 2 at Grandview Pleasure Point

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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St. Michael's Premier in Town Summer Cottage!, holiday rental in Tilghman

St. Michael's Premier in Town Summer Cottage!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!, holiday rental in Tilghman

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Property, Kayaks, Private Dock, Near Town, holiday rental in Tilghman

Waterfront Property, Kayaks, Private Dock, Near Town

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cottage 1a at Grandview Pleasure Point, holiday rental in Tilghman

Cottage 1a at Grandview Pleasure Point

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cottage 1b at Grandview Pleasure Point, holiday rental in Tilghman

Cottage 1b at Grandview Pleasure Point

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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St. Michaels Area Cottage - Walk to Water & Marina, holiday rental in Tilghman

St. Michaels Area Cottage - Walk to Water & Marina

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Indoor pool and spa located in beautiful Southern Maryland woodlands, holiday rental in Tilghman

Indoor pool and spa located in beautiful Southern Maryland woodlands

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Coastal Pet-Friendly Cottage <½ Mi to Beaches, holiday rental in Tilghman

NEW! Coastal Pet-Friendly Cottage <½ Mi to Beaches

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Bay Cottage Resort, holiday rental in Tilghman

Bay Cottage Resort

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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