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St. Michaels, MD Holiday Rentals
Holiday Rentals
USA
Maryland (MD)
Talbot County
St. Michaels, MD Holiday Rentals
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St. Michaels
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Amenities
Internet or Wifi (37)
Air Conditioning (36)
Washer/Dryer (33)
Grill (27)
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Suitability
Kid friendly (36)
Pet friendly (22)
Smoking allowed (1)
Wheelchair access (0)
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Property type
Holiday Rental House (33)
Condominium/Apartment (4)
Cabin Holiday Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (18)
Boat Available (3)
Private Chef (0)
Private Beach (0)
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Distance from
5 km
Chesapeake Bay Maritime Museum
1879 Hooper Strait Lighthouse
Tilghman Island
Saint Michaels Winery
LYON RUM Distillery
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37 rentals
in St. Michaels.
Stay in the HEART of Saint Michaels!
96
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
40
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps
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John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
104
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 5
Match:
Sleeps
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Walk to Everything House
30
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
129
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps
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Dollhouse in Central Historic St Michaels
22
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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St. Michael's Premier In-Town Rental with heated pool-opens 4/22
25
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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Chase Away the Chill with Our Winter Stay Specials!
12
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
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Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
15
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Chic Flat with King Bed & Fireplace
24
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 3
Match:
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Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
104
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 5
Match:
Sleeps
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Harbor View Suite
17
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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2025 Renovation Beautiful Waterfront Home w/ Pool In St. Michaels
4
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
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Downtown St. Michaels | Bikes | Kayaks | Private Pier
11
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
10
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Seasonal Rental: Artisan designed 3 bedroom home.
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Warm Up Here! Your Winter Getaway Awaits
8
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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Grace Cottage, Saint Michaels Walk to everything!
4
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 4
Match:
Sleeps
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Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
6
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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A Winter Getaway At This Waterfront Retreat
1
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL
5
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 6
Match:
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Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court
3
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
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Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub
2
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
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ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms
10
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
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TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool
10
Holiday Rental House
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6 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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Luxury Waterfront with pool and deep water dock, minutes from St Michaels.
2
Holiday Rental House
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4 bedrooms
5 bathrooms
Sleeps 8
Match:
Sleeps
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Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
11
Holiday Rental House
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7 bedrooms
4 bathrooms
Sleeps 9
Match:
Sleeps
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Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C
7
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 10
Match:
Sleeps
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Minutes from Downtown St. Michaels | Private Dock | Kayaks | 1000 Ft of Shorelin
10
Holiday Rental House
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5 bedrooms
6 bathrooms
Sleeps 9
Match:
Sleeps
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Classic Eastern Shore Waterfront Manor House - ST-936
20
Holiday Rental House
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6 bedrooms
5 bathrooms
Sleeps 12
Match:
Sleeps
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Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours
1
Holiday Rental House
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6 bedrooms
6 bathrooms
Sleeps 12
Match:
Sleeps
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Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur
Holiday Rental House
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6 bedrooms
6 bathrooms
Sleeps 12
Match:
Sleeps
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Come and get cozy at this Waterfront Escape
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
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Warm their hearts with a valentine getaway!
1
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 4
Match:
Sleeps
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Warm their heart with a valentine getaway!
Condo/Apartment
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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
3
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Bateau Cabin one of three Cove Cabins in St Michaels
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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1
Showing results 1-37 of 37
Frequently Asked Questions about St. Michaels
What are the best pet friendly rentals in St. Michaels?
The best pet friendly rentals in St. Michaels are:
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!
Walk to Everything House
See all pet friendly holiday rentals in St. Michaels on Tripadvisor
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