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Vacation Rentals and Cottages in St. Michaels, MD
Vacation Rentals
USA
Maryland (MD)
Talbot County
St. Michaels Vacation Rentals
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Bedrooms
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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 (21)
Wheelchair access (0)
Elder access (0)
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Property type
Vacation Rental House (33)
Condominium/Apartment (4)
Cabin Vacation Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (17)
Boat Available (3)
Private Chef (0)
Private Beach (0)
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Distance from
5 mi
Chesapeake Bay Maritime Museum
1879 Hooper Strait Lighthouse
Tilghman Island
LYON RUM Distillery
Saint Michaels Winery
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37 rentals
in St. Michaels.
Stay in the HEART of Saint Michaels!
93
Rental Home
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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
38
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 5
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Delightful Close to town
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
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John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
102
Rental Home
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2 bedrooms
3 bathrooms
Sleeps 5
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Walk to Everything House
29
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
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Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
128
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps
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Dollhouse in Central Historic St Michaels
22
Rental Home
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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 - Pool is open!
23
Rental Home
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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:
Sleeps
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Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
16
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Chic Flat with King Bed & Fireplace
25
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 3
Match:
Sleeps
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Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
103
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 5
Match:
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Harbor View Suite
13
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
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Beautiful Waterfront Home w/ Pool In St. Michaels
4
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
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Downtown St. Michaels | Bikes | Kayaks | Private Pier
11
Rental Home
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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
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Seasonal Rental: Artisan designed 3 bedroom home.
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Warm Up Here! Your Winter Getaway Awaits
6
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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Grace Cottage, Saint Michaels Walk to everything!
3
Rental Home
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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
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Unwind at this Waterfront Retreat
1
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
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LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL
3
Rental Home
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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
2
Rental Home
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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
1
Rental Home
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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
Rental Home
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6 bedrooms
3 bathrooms
Sleeps 8
Match:
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Luxury Waterfront with pool and deep water dock, minutes from St Michaels.
2
Rental Home
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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!
9
Rental Home
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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
Rental Home
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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
Rental Home
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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
Rental Home
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6 bedrooms
5 bathrooms
Sleeps 12
Match:
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Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours
1
Rental Home
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6 bedrooms
6 bathrooms
Sleeps 12
Match:
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Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur
Rental Home
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6 bedrooms
6 bathrooms
Sleeps 12
Match:
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Celebrate the Season! Cozy Waterfront Escape
Rental Home
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3 bedrooms
4 bathrooms
Sleeps 6
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2BR Waterfront Family Escape
Rental Home
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2 bedrooms
3 bathrooms
Sleeps 4
Match:
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Couples Retreat, 2 King Bedrooms!
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
2
Rental Home
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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
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
Match:
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1
Showing results 1-37 of 37
Frequently Asked Questions about St. Michaels
Do any vacation rentals in St. Michaels have a pool?
Yes, here are some popular vacation 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
Delightful Close to town
See all vacation rentals with a pool in St. Michaels on Tripadvisor
Do any vacation rentals in St. Michaels have internet access?
Yes, here are some popular vacation 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
Delightful Close to town
See all vacation rentals in St. Michaels on Tripadvisor
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 vacation rentals in St. Michaels on Tripadvisor
What are some great rentals in St. Michaels that are kid friendly?
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
Delightful Close to town
See all kid friendly vacation rentals in St. Michaels on Tripadvisor
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