St. Michaels Holiday Apartments
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50 rentals in St. Michaels.
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Waterview Cottage In St. Michaels!
2 bedrooms
3 bathrooms
Sleeps 5
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TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!
5 bedrooms
3 bathrooms
Sleeps 8
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Premier Cottage in St. Michaels- In Town Location!
2 bedrooms
2 bathrooms
Sleeps 5
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*****Waterfront home w/ pool in St. Michaels
4 bedrooms
3 bathrooms
Sleeps 8
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Location Location! St Michaels-- In Town Cottage!
2 bedrooms
2 bathrooms
Sleeps 5
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Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!
2 bedrooms
2 bathrooms
Sleeps 5
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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
4 bedrooms
3 bathrooms
Sleeps 8
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Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX
1 bedroom
1 bathroom
Sleeps 6
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St. Michael's Premier in Town Summer Cottage!
2 bedrooms
2 bathrooms
Sleeps 4
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Waterfront Property, Kayaks, Private Dock, Near Town
3 bedrooms
3 bathrooms
Sleeps 6
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Bay Cottage Resort
6 bedrooms
5 bathrooms
Sleeps 12
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Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
7 bedrooms
9 bathrooms
Sleeps 20
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New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks
5 bedrooms
4 bathrooms
Sleeps 10
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Enhanced Cleaning & Disinfecting. Private Beach Volleyball Court. Walk to Beach.
4 bedrooms
3 bathrooms
Sleeps 12
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Comfy home on beautiful Leadenham Creek. Book now for summer!
5 bedrooms
4 bathrooms
Sleeps 10
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Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway
2 bedrooms
2 bathrooms
Sleeps 4
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Stunning Views of the Bay - Waterfront
3 bedrooms
4 bathrooms
Sleeps 10
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Beautiful Tidewater home between Easton & ST Michaels!
4 bedrooms
7 bathrooms
Sleeps 8
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Escape To This Oxford, Md Waterfront Home - Kayaking, Canoeing & Relaxing
4 bedrooms
5 bathrooms
Sleeps 8
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St. Michael's Waterfront Vacation Home
5 bedrooms
5 bathrooms
Sleeps 12
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Fully remodel 2 bedroom country cottage.
2 bedrooms
2 bathrooms
Sleeps 4
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Waterfront Getaway on the Choptank River
2 bedrooms
1 bathroom
Sleeps 6
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Charming 3 Bedroom 3 Bath Beach Front Property
3 bedrooms
3 bathrooms
Sleeps 12
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Gorgeous Sunsets and Chesapeake Charm
3 bedrooms
3 bathrooms
Sleeps 6
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Holidays at the Cove - plenty of space to gather while making memories
5 bedrooms
7 bathrooms
Sleeps 10
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Eastern Shore Getaway Near St. Michaels
1 bedroom
2 bathrooms
Sleeps 2
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Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton
5 bedrooms
4 bathrooms
Sleeps 10
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Relax in Tilghman Island
4 bedrooms
2 bathrooms
Sleeps 6
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New Modern Waterfront Farmhouse Built 2018
4 bedrooms
4 bathrooms
Sleeps 10
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Enhanced Cleaning and Disinfecting. Million$ Chesapeake Bay Sunsets by the Bay.
4 bedrooms
2 bathrooms
Sleeps 8
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Holiday on the Bay, Kent Island Beach House
4 bedrooms
2 bathrooms
Sleeps 10
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Main House at Grandview at Pleasure Point
5 bedrooms
3 bathrooms
Sleeps 13
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Oxford Waterfront Cottage-Walk to Town, Kayak, Dock, and Bikes
3 bedrooms
2 bathrooms
Sleeps 6
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KI Golf House-A PAR for the Course & Mile to Beach
4 bedrooms
3 bathrooms
Sleeps 10
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3BR 1BA Private Beach / Pool / Boat Launch / Pier / Golf Cart and much more!
3 bedrooms
1 bathroom
Sleeps 10
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Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)
4 bedrooms
2 bathrooms
Sleeps 8
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Not to early to think about joining us this Spring and Summer.
4 bedrooms
3 bathrooms
Sleeps 8
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Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview
5 bedrooms
5 bathrooms
Sleeps 10
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Cottage 2 at Grandview Pleasure Point
2 bedrooms
1 bathroom
Sleeps 6
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BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa
3 bedrooms
4 bathrooms
Sleeps 6
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Cottage 1a at Grandview Pleasure Point
1 bedroom
1 bathroom
Sleeps 4
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Cottage 1b at Grandview Pleasure Point
1 bedroom
1 bathroom
Sleeps 2
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Tranquil Easton Waterfront Property
3 bedrooms
4 bathrooms
Sleeps 6
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Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina
4 bedrooms
2 bathrooms
Sleeps 12
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St. Michaels Area Cottage - Walk to Water & Marina
2 bedrooms
2 bathrooms
Sleeps 4
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Chesapeake Bay Waterfront ARTectural Home
3 bedrooms
5 bathrooms
Sleeps 10
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Private waterfront estate with pool, convenient to Easton and St. Michaels
5 bedrooms
5 bathrooms
Sleeps 10
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Abay Palace of Kent Narrows in a King Bed
1 bedroom
1 bathroom
Sleeps 5
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New-Kent Island House with Pool and Bay Views!
3 bedrooms
3 bathrooms
Sleeps 13
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Frequently Asked Questions about St. Michaels
- Yes, here are some popular holiday rentals in St. Michaels that have a pool:
- Sandy Pines: Enjoy Harris Creek w/Pool and Boats
- *****Waterfront home w/ pool in St. Michaels
- TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!
- Yes, here are some popular holiday rentals in St. Michaels that have internet access:
- Large Historic Thomas Harrison House on Harbor in St. Michaels Town
- Premier Cottage in St. Michaels- In Town Location!
- Location Location! St Michaels-- In Town Cottage!
- Some of the most popular kid friendly rentals in St. Michaels are:
- Large Historic Thomas Harrison House on Harbor in St. Michaels Town
- Premier Cottage in St. Michaels- In Town Location!
- Location Location! St Michaels-- In Town Cottage!