St. Michaels Holiday Rentals
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37 rentals in St. Michaels.
Stay in the HEART of Saint Michaels!
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Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
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John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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Walk to Everything House
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Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
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Dollhouse in Central Historic St Michaels
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St. Michael's Premier In-Town Rental with heated pool-opens 4/22
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Chase Away the Chill with Our Winter Stay Specials!
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Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
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Chic Flat with King Bed & Fireplace
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Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
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Harbor View Suite
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2025 Renovation Beautiful Waterfront Home w/ Pool In St. Michaels
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Downtown St. Michaels | Bikes | Kayaks | Private Pier
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Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
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Seasonal Rental: Artisan designed 3 bedroom home.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Warm Up Here! Your Winter Getaway Awaits
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Grace Cottage, Saint Michaels Walk to everything!
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Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
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A Winter Getaway At This Waterfront Retreat
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LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL
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Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court
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Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub
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ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms
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TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool
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Luxury Waterfront with pool and deep water dock, minutes from St Michaels.
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Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
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Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C
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Minutes from Downtown St. Michaels | Private Dock | Kayaks | 1000 Ft of Shorelin
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Classic Eastern Shore Waterfront Manor House - ST-936
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Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours
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Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur
Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Warm their hearts with a valentine getaway!
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Warm their heart with a valentine getaway!
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lovely Cottage in St.Michael’s.Dock 7‘ Depth,Pet Friendly. A VIP Vacation Rental
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Bateau Cabin one of three Cove Cabins in St Michaels
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Come and get cozy at this Waterfront Escape
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-37 of 37
Frequently Asked Questions about St. Michaels
- Yes, here are some popular holiday rentals in St. Michaels that have a pool:
- Stay in the HEART of Saint Michaels!
- Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
- John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
- Yes, here are some popular holiday rentals in St. Michaels that have internet access:
- Stay in the HEART of Saint Michaels!
- Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
- John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
- Some of the most popular kid friendly rentals in St. Michaels are:
- Stay in the HEART of Saint Michaels!
- Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
- John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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