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Cottages and homes in St. Michaels, MD and nearby

All 15 Rentals in the St. Michaels Area
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$375
/ Night
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1 / 22
5 of 5 stars (1) Excellent
St. Michaels
4 Bedrooms / 3 Bathrooms / Sleeps 10
travelers have booked this property
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From
$759
/ Night
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1 / 38
St. Michaels
6 Bedrooms / 6 Bathrooms / Sleeps 12
travelers have booked this property
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$450
/ Night
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1 / 13
5 of 5 stars (5) Excellent
St. Michaels
3 Bedrooms / 3 Bathrooms / Sleeps 10
travelers have booked this property
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From
$290
/ Night
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1 / 23
5 of 5 stars (2) Excellent
St. Michaels
7 Bedrooms / 3 Bathrooms / Sleeps 11
Overview Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The historic Thomas Harrison House is located on the harbor in the center of the town of St. Michaels. This Eastern Shore/Chesapeake Bay vacation rental has magnificent water VIEWS and can accomodate up to 12 people. The house is a short walk from all the museums, parks, restaurants, churches, and... View all property information
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5 of 5 stars Reviewed September 27, 2014
Friends and family stayed at the home to watch my nephew get married on 9/20/14. I must say, the house was as much of the event as the wedding celebration. We went from 6 of us...
5 of 5 stars Reviewed July 23, 2014
Our daughter was married at the Tidewater Inn in Easton. We rented this lovely, large home the week before the wedding to have a place for the bride to relax while we spent time...
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From
$160
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1 / 13
5 of 5 stars (1) Excellent
St. Michaels
2 Bedrooms / 1 Bathroom / Sleeps 4
Overview Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The historic Thomas Blades House is a 2 bedroom, 2 bathroom vacation cottage that is a short walk from all museums, parks, restaurants, churches and shops in St. Michaels. The house was built around 1850 by Thomas Blades, a young sailor. The first floor of the original portion of the Blades... View all property information
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5 of 5 stars Reviewed August 18, 2014
Location location location! Walk to perhaps the cutest town ever! Friendly people ,dog loving community, sail boats, restaurants and such a lovely little town.. Perfection found!
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From
$150
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1 / 20
5 of 5 stars (12) Excellent
St. Michaels
2 Bedrooms / 1 Bathroom / Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
The historic Washington Melson House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from all museums, parks, restaurants, churches and shops in St. Michaels. The house was built around 1840 by Washington Melson, a sailor, believed to be one of two individuals in Talbot County... View all property information
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5 of 5 stars Reviewed August 22, 2014
The pictures of this house do not lie. It is that nice. We parked our car and didn't need again until we left. Close to everything. Walk to the water , sit on the bench and...
5 of 5 stars Reviewed July 20, 2014
We fully enjoyed our relaxing stay in the sleepy little town of St. Michaels, and would definitely return when given the chance. The location is perfect - within a one block walk...
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From
$280
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1 / 9
St. Michaels
3 Bedrooms / 3 Bathrooms / Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
You can tell right away, from the warm sage green exterior and the peaceful creekside setting, that this charming vacation cottage promises a fun, relaxing getaway. With a 180 degree expanse of spectacular Oak Creek waterfront, the River House at Royal Oak is the pefect choice for year 'round... View all property information
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The following rentals are within 10 miles of St. Michaels, Maryland.

From
$175
/ Night
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1 / 20
5 of 5 stars (3) Excellent
Tilghman
3 Bedrooms / 2 Bathrooms / Sleeps 6
travelers have booked this property
Overview Reviews (3) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Enjoy the beauty and tranquility of Tilghman Island from this bright and comfortable 3 bedroom, 2 bathroom cottage known for many years as the vacation rental 'The Roost.' Available for both short and long-term rentals, the cottage is located on a quiet residential street across from a marina... View all property information
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From
$75
/ Night
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1 / 21
Tilghman
2 Bedrooms / 1 Bathroom / Sleeps 6
Overview Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Get away and stay in our cozy cottage that sits on the Knapp's Narrows in Tilghman, MD. Captain's Watch is a Waterfront Cottage which has a screened porch with beautiful sunrise view of Knapps Narrows. It is nestled in a Working Watermens Village, 12 miles from Historic St. Michaels, Maryland on... View all property information
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From
$250
/ Night
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1 / 12
Easton
2 Bedrooms / 1 Bathroom / Sleeps 4
Overview Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Exclusive 2 bedroom upstairs waterfront apartment with private entrance located 20 minutes from historic Easton and St. Michaels and 30 minutes from Oxford. Enjoy the sunrise each morning on your own private deck overlooking one of the most peaceful and unique surroundings the Eastern Shore has to... View all property information
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From
$1,500
/ Night
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1 / 7
Oxford
Studio / 4 Bathrooms / Sleeps 6
Overview Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Fishing...
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Secluded, tranquil home located on the water, between Easton and Oxford, Maryland. Includes five bedrooms, four bathrooms, fully equipped kitchen, sun porch, swimming pool and tennis courts. Grounds include private driveway, miles of walking paths, and dock with two kayaks. View all property information
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From
$300
/ Night
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1 / 8
5 of 5 stars (1) Excellent
Tilghman
1 Bedroom / 1 Bathroom / Sleeps 3
Overview Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Watch the dazzling sunsets over the bay. Choose from our one bedroom Waterfront Cottages located on the Chesapeake Bay side of Tilghman Island: It is a beautiful 2-story one bedroom cottage with stunning views of the bay from the 2nd floor bedroom, with hardwood floors throughout, a full kitchen,... View all property information
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5 of 5 stars Reviewed July 17, 2014
Have stayed here two times. Once in the 2 bedroom and once in the one bedroom. Both facilities are clean and welcoming. Both properties provide beautiful views and easy access to...
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From
$375
/ Night
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1 / 9
5 of 5 stars (1) Excellent
Bozman
2 Bedrooms / 1 Bathroom / Sleeps 6
Overview Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Grill
  • Internet Access
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, valences, sofas, wing and lounge chairs and collectibles. All the cottages are fully furnished including solaria porch, gas... View all property information
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From
$665
/ Night
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1 / 7
5 of 5 stars (8) Excellent
Bozman
4 Bedrooms / 2 Bathrooms / Sleeps 13
Overview Reviews (8) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Beautiful NEW kitchen... Featuring two interior eating/serving areas, custom french windows that open to a sitting area on the porch, 4 bedrooms & Enclosed Sleeping Porch (2 queens, 1 double, daybed w/trundle, 5 twins) 2 ½ baths, fireplace, 3 TV’s, DVD, cable, wireless internet, large... View all property information
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From
$250
/ Night
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1 / 11
5 of 5 stars (1) Excellent
Claiborne
3 Bedrooms / 4 Bathrooms / Sleeps 8
Overview Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Beautiful like new waterfront home on the Chesapeake Bay, 5 minute drive to Historic St. Michaels. Minutes to many quaint watermen villages. Shared waterside pool, beach, kayaks, small boat, childrens playset. The property was designed to take advantage of the incredible views of the Chesapeake... View all property information
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5 of 5 stars Reviewed October 10, 2014
Very new, very clean, very spacious, very comfortable. The family thoroughly enjoyed our stay here with plenty of room to spread out, a huge kitchen, meals on the deck and...
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