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Holiday Homes in St. Michaels

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50 rentals in St. Michaels.
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Premier Cottage in St. Michaels- In Town Location!, holiday rental in St. Michaels

Premier Cottage in St. Michaels- In Town Location!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!, holiday rental in St. Michaels

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

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

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

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

Location Location! St Michaels-- In Town Cottage!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!, holiday rental in St. Michaels

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

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

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

7 bedrooms
4 bathrooms
Sleeps 9
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Sandy Pines:  Enjoy Harris Creek w/Pool and Boats, holiday rental in St. Michaels

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 St. Michaels

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 St. Michaels

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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St. Michael's Premier in Town Summer Cottage!, holiday rental in St. Michaels

St. Michael's Premier in Town Summer Cottage!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront Property, Kayaks, Private Dock, Near Town, holiday rental in St. Michaels

Waterfront Property, Kayaks, Private Dock, Near Town

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Bay Cottage Resort, holiday rental in St. Michaels

Bay Cottage Resort

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS), holiday rental in St. Michaels

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 St. Michaels

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Enhanced Cleaning & Disinfecting. Private Beach Volleyball Court. Walk to Beach., holiday rental in St. Michaels

Enhanced Cleaning & Disinfecting. Private Beach Volleyball Court. Walk to Beach.

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Comfy home on beautiful Leadenham Creek. Book now for summer!, holiday rental in St. Michaels

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

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Stunning Views of the Bay - Waterfront, holiday rental in St. Michaels

Stunning Views of the Bay - Waterfront

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Fully remodel 2 bedroom country cottage., holiday rental in St. Michaels

Fully remodel 2 bedroom country cottage.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Escape To This Oxford, Md Waterfront Home - Kayaking, Canoeing & Relaxing, holiday rental in St. Michaels

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

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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St. Michael's Waterfront Vacation Home, holiday rental in St. Michaels

St. Michael's Waterfront Vacation Home

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Tidewater home between Easton & ST Michaels!, holiday rental in St. Michaels

Beautiful Tidewater home between Easton & ST Michaels!

4 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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Charming 3 Bedroom 3 Bath Beach Front Property, holiday rental in St. Michaels

Charming 3 Bedroom 3 Bath Beach Front Property

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Gorgeous Sunsets and Chesapeake Charm, holiday rental in St. Michaels

Gorgeous Sunsets and Chesapeake Charm

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Relax in Tilghman Island, holiday rental in St. Michaels

Relax in Tilghman Island

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Getaway on the Choptank River, holiday rental in St. Michaels

Waterfront Getaway on the Choptank River

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Holidays at the Cove  - plenty of space to gather while making memories, holiday rental in St. Michaels

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

5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton, holiday rental in St. Michaels

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

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

Eastern Shore Getaway Near St. Michaels

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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New Modern Waterfront Farmhouse Built 2018, holiday rental in St. Michaels

New Modern Waterfront Farmhouse Built 2018

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Enhanced Cleaning and Disinfecting. Million$ Chesapeake Bay Sunsets by the Bay., holiday rental in St. Michaels

Enhanced Cleaning and Disinfecting. Million$ Chesapeake Bay Sunsets by the Bay.

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Holiday on the Bay, Kent Island Beach House, holiday rental in St. Michaels

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 St. Michaels

Main House at Grandview at Pleasure Point

5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Oxford Waterfront Cottage-Walk to Town, Kayak, Dock, and Bikes, holiday rental in St. Michaels

Oxford Waterfront Cottage-Walk to Town, Kayak, Dock, and Bikes

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private waterfront estate with pool, convenient to Easton and St. Michaels, holiday rental in St. Michaels

Private waterfront estate with pool, convenient to Easton and St. Michaels

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa, holiday rental in St. Michaels

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

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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KI Golf House-A PAR for the Course & Mile to Beach, holiday rental in St. Michaels

KI Golf House-A PAR for the Course & Mile to Beach

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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3BR 1BA Private Beach / Pool / Boat Launch / Pier / Golf Cart and much more!, holiday rental in St. Michaels

3BR 1BA Private Beach / Pool / Boat Launch / Pier / Golf Cart and much more!

3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Not to early to think about joining us this Spring and Summer., holiday rental in St. Michaels

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

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets), holiday rental in St. Michaels

Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview, holiday rental in St. Michaels

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 St. Michaels

Cottage 2 at Grandview Pleasure Point

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Abay Palace of Kent Narrows in a King Bed, holiday rental in St. Michaels

Abay Palace of Kent Narrows in a King Bed

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Cottage 1a at Grandview Pleasure Point, holiday rental in St. Michaels

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 St. Michaels

Cottage 1b at Grandview Pleasure Point

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tranquil Easton Waterfront Property, holiday rental in St. Michaels

Tranquil Easton Waterfront Property

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina, holiday rental in St. Michaels

Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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St. Michaels Area Cottage - Walk to Water & Marina, holiday rental in St. Michaels

St. Michaels Area Cottage - Walk to Water & Marina

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Private setting, enjoy nature, kayaking and total relaxation, holiday rental in St. Michaels

Private setting, enjoy nature, kayaking and total relaxation

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Chesapeake Bay Waterfront ARTectural Home, holiday rental in St. Michaels

Chesapeake Bay Waterfront ARTectural Home

3 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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New-Kent Island House with Pool and Bay Views!, holiday rental in St. Michaels

New-Kent Island House with Pool and Bay Views!

3 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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