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Featured listings
Whale Tail Farm, Easton
- $1,576 - $5,312/night
- $2,873 - $6,462/week
- Bedrooms: 5, sleeps 10
- Bathrooms: 4
- Contact Manager
Price:
Blue Gates, Easton
- $1,912 - $4,072/night
- $3,712 - $4,912/week
- Bedrooms: 4, sleeps 8
- Bathrooms: 5
- Contact Manager
Price:
Cod's Point, Easton
- $1,099 - $2,599/night
- $1,849 - $3,099/week
- Bedrooms: 4, sleeps 12
- Bathrooms: 4
- Contact Manager
Price:
Cedar Point, Easton
- $883 - $2,505/night
- $1,524 - $3,018/week
- Bedrooms: 3, sleeps 8
- Bathrooms: 2
- Contact Manager
Price:
Graceful View, Easton
- $485 - $1,085/night
- $785 - $1,285/week
- Bedrooms: 3, sleeps 6
- Bathrooms: 2
- Contact Manager
Price:
Caulk's Cove, Easton
- $730 - $1,620/night
- $1,315 - $1,940/week
- Bedrooms: 4, sleeps 8
- Bathrooms: 3
- Contact Manager
Price:
My Blue Heron, Easton
- $835 - $1,915/night
- $1,375 - $2,275/week
- Bedrooms: 4, sleeps 8
- Bathrooms: 3
- Contact Manager
Price:
Macks Landing, Easton
- $821 - $1,963/night
- $1,328 - $2,333/week
- Bedrooms: 3, sleeps 6
- Bathrooms: 2
- Contact Manager
Price:
Sunset Bay, Easton
- $1,721 - $5,293/night
- $2,961 - $6,393/week
- Bedrooms: 5, sleeps 16
- Bathrooms: 3
- Contact Manager
Price:
Pandion, Easton
- $817 - $1,817/night
- $1,357 - $2,157/week
- Bedrooms: 3, sleeps 5
- Bathrooms: 2
- Contact Manager
Price:
Recommended by Travelers
There are no vacation rentals within Saint Michaels, Maryland. We broadened your search to include all rentals within 25 miles.
Waterfront Chespeake Bay Retreat, Cambridge
Nightly rate from
$399
$399
| Management: | Verified Plus owner |
| Property: | Rental Home |
| Bedrooms: | 6, sleeps 16 |
| Bathrooms: | 5 |
| Min stay: | 3 |
New premier waterfront vacation home - 6bed / 5bath home w/ beach & heated pool. All of this on over 3 acres and +- 400 feet of stunning waterfront
Near ...
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Nightly
$399 - $699 -
Weekly
$2,500 - $4,700 -
Monthly
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Stunning, New Chesapeake Waterfront Rental, Cambridge
Nightly rate from
$399
$399
| Management: | Verified Plus owner |
| Property: | Rental Home |
| Bedrooms: | 5, sleeps 14 |
| Bathrooms: | 5 |
| Min stay: | 3 |
Fabulous, new premier vacation home on 500 feet of Chesapeake waterfront. A gorgeous home; beach, dock, pool, boats, bikes, porches & mile-wide view
...
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Nightly
$399 - $699 -
Weekly
$2,600 - $4,800 -
Monthly
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Also consider
The Strand, Easton
Nightly rate from
$576
$576
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 3, sleeps 6 |
| Bathrooms: | 3 |
This darling 3 bedroom cottage sits on a corner lot on the lovely Oxford Strand. With the Tred Avon straight ahead and a 100' sandy beach for play, this ...
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Nightly
$576 - $1,460 -
Weekly
$1,018 - $1,755 -
Monthly
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Windswept on the Choptank, Cambridge
Nightly rate from
$199
$199
| Management: | Verified owner |
| Property: | Rental Home |
| Bedrooms: | 4, sleeps 12 |
| Bathrooms: | 3 |
| Min stay: | 2 |
Rare Choptank River home available in Cambridge's finest neighborhood
4bedrms / 3baths w/ 250 feet of stunning waterfront and sweeping lawns
Unique, private ...
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Nightly
$199 - $399 -
Weekly
$999 - $2,499 -
Monthly
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Also consider
Lee Haven, Easton
Nightly rate from
$1,655
$1,655
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 5, sleeps 12 |
| Bathrooms: | 5 |
This family compound has it all, 5 bedrooms, 4 1/2 baths, pool, dock, close to St Michaels and Easton and situated off of the Tred Avon. Wonderful quiet lane ...
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Nightly
$1,655 - $4,491 -
Weekly
$2,895 - $5,407 -
Monthly
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Bushey Heath Farm, Easton
Nightly rate from
$775
$775
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 4, sleeps 8 |
| Bathrooms: | 2 |
The best of both worlds come with this Classic Cape Cod waterfront home. Conveniently located just minutes to St. Michaels for all the activities you desire, ...
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Nightly
$775 - $2,725 -
Weekly
$1,453 - $3,325 -
Monthly
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Miles Aweigh, Easton
Nightly rate from
$943
$943
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 3, sleeps 6 |
| Bathrooms: | 3 |
Miles Aweigh is a special property that offers all the comfort and privacy of an estate home--the pool, the private deep water dock, three queen en suite ...
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Nightly
$943 - $2,507 -
Weekly
$1,676 - $3,020 -
Monthly
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Pier Street, Easton
Nightly rate from
$600
$600
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 3, sleeps 7 |
| Bathrooms: | 3 |
Pier Street is a newly painted, landscaped and decorated home designed for a fun getaway. Located in the heart of Oxford and directly across from The Pier ...
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Nightly
$600 - $1,760 -
Weekly
$1,500 - $2,200 -
Monthly
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Also consider
Green Shadow Barn, Easton
Nightly rate from
$2,049
$2,049
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 4, sleeps 6 |
| Bathrooms: | 3 |
Living in a "Barn" has never been so luxurious. 700' of shoreline, a deep water dock and a waterfront pool are only the beginning to this beautiful 4,000 ...
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Nightly
$2,049 - $4,649 -
Weekly
$4,149 - $5,649 -
Monthly
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Crabbiest Cottage, Easton
Nightly rate from
$710
$710
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 3, sleeps 6 |
| Bathrooms: | 3 |
There is nothing to be crabby about when staying at this restful spot just outside St. Michaels. Comfortably furnished yet priced for the budget conscious ...
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Nightly
$710 - $1,600 -
Weekly
$1,295 - $1,920 -
Monthly
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Mariner's Point, Easton
Nightly rate from
$580
$580
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 3, sleeps 6 |
| Bathrooms: | 3 |
This 1,900 square foot duplex sits at the Eastern opening of the Chesapeake Bay. Surrounded by water you will enjoy some of the broadest westerly views in ...
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Nightly
$580 - $1,080 -
Weekly
$1,030 - $1,280 -
Monthly
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Willows on the Miles, Easton
Nightly rate from
$1,610
$1,610
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 6, sleeps 11 |
| Bathrooms: | 3 |
A renovated farmhouse, Willows on the Miles offers the ambience of an old home with the luxury of a newly renovated property. Baths, kitchen and all rooms are ...
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Nightly
$1,610 - $4,446 -
Weekly
$2,850 - $5,362 -
Monthly
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Quarter Cove, Easton
Nightly rate from
$932
$932
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 4, sleeps 8 |
| Bathrooms: | 3 |
Policy: Pets allowed
Minimum Stay: 2
Check-In: 4pm
Check-Out: 10am
Policy: Pets allowed
Minimum Stay: 2
Check-In: 4pm
Check-Out: 10am
-
Nightly
$932 - $2,770 -
Weekly
$1,653 - $3,350 -
Monthly
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Hudson Manor, Easton
Nightly rate from
$1,155
$1,155
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 5, sleeps 15 |
| Bathrooms: | 3 |
Linens & Towels Provided - Can Be Rented Internet Access - Yes Owner provides an aircard to guest Privacy Rating 5* -**** Pet Friendly - Yes Central Air - ...
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Nightly
$1,155 - $3,255 -
Weekly
$2,205 - $3,955 -
Monthly
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Also consider
Winter Bottom Point, Easton
Nightly rate from
$810
$810
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 3, sleeps 6 |
| Bathrooms: | 4 |
At the end of a meandering lane lies this adorable home waiting for you and your family to discover our Eastern Shore lifestyle! This charming home has been ...
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Nightly
$810 - $1,890 -
Weekly
$1,350 - $2,250 -
Monthly
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Captain's Cove, Easton
Nightly rate from
$1,599
$1,599
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 5, sleeps 10 |
| Bathrooms: | 5 |
Captains Cove is a classic Eastern Shore Home that oozes charm and provides a quiet escape, with unexpected touches, such as a firepit for roasting ...
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Nightly
$1,599 - $5,171 -
Weekly
$2,839 - $6,271 -
Monthly
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Choptank Cottage, Easton
Nightly rate from
$678
$678
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 3, sleeps 6 |
| Bathrooms: | 3 |
This charming cottage is the ideal place for a couple or small group looking for respite and relaxation. On the outskirts of Tilghman Island, come to Choptank ...
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Nightly
$678 - $1,320 -
Weekly
$1,170 - $1,570 -
Monthly
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Swan Harbor, Easton
Nightly rate from
$710
$710
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 4, sleeps 8 |
| Bathrooms: | 3 |
Uniquely located within walking distance of St. Michaels and on the Miles River, Swan Harbor provides its guests the best of both worlds. Imagine a morning ...
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Nightly
$710 - $1,820 -
Weekly
$1,265 - $2,190 -
Monthly
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Cabin Cove Manor, Easton
Nightly rate from
$1,124
$1,124
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 4, sleeps 8 |
| Bathrooms: | 4 |
Sprawling over several acres with sweeping views of Eastern Bay, Cabin Cove Manor is the perfect setting for your next family celebration or getaway with ...
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Nightly
$1,124 - $3,318 -
Weekly
$1,913 - $3,998 -
Monthly
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Also consider
Neavitt Manor, Easton
Nightly rate from
$784
$784
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 3, sleeps 6 |
| Bathrooms: | 2 |
A quiet cottage with all the amenities of an estate. Neavitt Manor offers the smaller group a waterfront home with private pool and new dock Brightly ...
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Nightly
$784 - $2,246 -
Weekly
$1,291 - $2,696 -
Monthly
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St Michaels Waterfronts
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Professionally managed typically means…
- Member of the FlipKey Verified Property Manager program
- Dedicated on-site help
- Experienced local staff
- Professional hospitality services
- Secure credit card payment
Verified Plus property owner typically means…
- Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
- Established history of renting online
- Direct & personal contact
- Detailed rental knowledge
- Flexible dates & rates
- More options in smaller towns
Verified property owner typically means…
- Verification of owner name and address via valid credit card
- History of renting online
- Direct & personal contact
- Detailed rental knowledge
- Flexible dates & rates
- More options in smaller towns
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