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Saint Michaels Vacation Rentals
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Featured listings
Simplicity Cottage, Easton
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Price:
€498 - €834/night
€1,003/week
- Bedrooms: 2, sleeps 4
- Bathrooms: 1 Contact Manager
Harbor Hideaway, Easton
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Price:
€410 - €653/night
€774 - €791/week
- Bedrooms: 2, sleeps 4
- Bathrooms: 2 Contact Manager
Martini Cottage, Easton
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Price:
€269 - €673/night
€673 - €841/week
- Bedrooms: 2, sleeps 4
- Bathrooms: 1 Contact Manager
Up The Creek, Easton
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Price:
€592 - €1,318/night
€955 - €1,561/week
- Bedrooms: 3, sleeps 7
- Bathrooms: 3 Contact Manager
Sunset Bay, Easton
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Price:
€1,158 - €3,562/night
€1,993 - €4,302/week
- Bedrooms: 5, sleeps 16
- Bathrooms: 3 Contact Manager
Pandion, Easton
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Price:
€550 - €1,223/night
€913 - €1,452/week
- Bedrooms: 3, sleeps 5
- Bathrooms: 2 Contact Manager
Easton Hideaway, Easton
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Price:
€495 - €1,289/night
€798 - €1,538/week
- Bedrooms: 3, sleeps 6
- Bathrooms: 2 Contact Manager
Miles Aweigh, Easton
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Price:
€635 - €1,687/night
€1,128 - €2,032/week
- Bedrooms: 3, sleeps 6
- Bathrooms: 3 Contact Manager
Pier Street, Easton
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Price:
€404 - €1,184/night
€1,009 - €1,480/week
- Bedrooms: 3, sleeps 7
- Bathrooms: 3 Contact Manager
Mariner's Point, Easton
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Price:
€390 - €727/night
€693 - €861/week
- Bedrooms: 3, sleeps 6
- Bathrooms: 3 Contact Manager
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
€269
€269
| 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
€269 - €470 -
Weekly
€1,682 - €3,163 -
Monthly
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Stunning, New Chesapeake Waterfront Rental, Cambridge
Nightly rate from
€269
€269
| 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
€269 - €470 -
Weekly
€1,750 - €3,230 -
Monthly
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Also consider
Windswept on the Choptank, Cambridge
Nightly rate from
€134
€134
| 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
€134 - €269 -
Weekly
€672 - €1,682 -
Monthly
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The Strand, Easton
Nightly rate from
€388
€388
| 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
€388 - €983 -
Weekly
€685 - €1,181 -
Monthly
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Also consider
Lee Haven, Easton
Nightly rate from
€1,114
€1,114
| 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
€1,114 - €3,022 -
Weekly
€1,948 - €3,639 -
Monthly
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Bushey Heath Farm, Easton
Nightly rate from
€522
€522
| 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
€522 - €1,834 -
Weekly
€978 - €2,238 -
Monthly
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East Bonfield Farm, Easton
Nightly rate from
€993
€993
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 4, sleeps 8 |
| Bathrooms: | 3 |
Ever wish you could step back in time? Just for a little while? At East Bonfield, you will feel transformed to an easier time, when kids played freely and ...
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Nightly
€993 - €3,179 -
Weekly
€1,752 - €3,852 -
Monthly
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River House on Moon Bay, Easton
Nightly rate from
€552
€552
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 4, sleeps 8 |
| Bathrooms: | 3 |
The ever-changing Chester River is the focal point ofthe house. Watermen called this section of the riverœMoon Bay,? hence the name The River House on ...
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Nightly
€552 - €1,135 -
Weekly
€843 - €1,330 -
Monthly
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Also consider
River Marsh Condominium, Easton
Nightly rate from
€483
€483
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 2, sleeps 4 |
| Bathrooms: | 2 |
Linens & Towels Provided - Yes Beds Made upon Arrival - Yes Internet Access - Yes Grill - Charcoal Community Grill Privacy Rating 1* - *** Pet Friendly - Yes ...
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Nightly
€483 - €6,291 -
Weekly
€981 - €1,143 -
Monthly
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Captain's Quarters, Easton
Nightly rate from
€1,366
€1,366
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 7, sleeps 24 |
| Bathrooms: | 7 |
This home is fabulous for larger family get togethers or adult retreats for all seasons This expansive 5,000 + square foot home sits on over 3 acres of which ...
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Nightly
€1,366 - €4,427 -
Weekly
€2,429 - €5,369 -
Monthly
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Three Sheets to the Wind, Easton
Nightly rate from
€410
€410
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 4, sleeps 8 |
| Bathrooms: | 2 |
Escape from the bustle of everyday life, hang your keys on the rack, let the kids and dogs romp freely, and soak in the many pleasures of Tilghman Island ...
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Nightly
€410 - €747 -
Weekly
€713 - €882 -
Monthly
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Barth's Cottage, Easton
Nightly rate from
€562
€562
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 3, sleeps 8 |
| Bathrooms: | 3 |
Barth's cottage is perfectly situated between St Michaels and Easton, waterfront just minutes from The Miles River off of Newcomb Creek. On almost 3 acres ...
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Nightly
€562 - €1,874 -
Weekly
€1,018 - €2,278 -
Monthly
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Sunrise Cove, Easton
Nightly rate from
€536
€536
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 3, sleeps 8 |
| Bathrooms: | 3 |
This spacious 2,500 square foot homes sits on 2 acres overlooking Solitude Creek. With a private dock and pool/hot tub you have everything you need for a ...
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Nightly
€536 - €1,847 -
Weekly
€991 - €2,251 -
Monthly
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Pines at Barrett Cove, Easton
Nightly rate from
€569
€569
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 2, sleeps 4 |
| Bathrooms: | 3 |
Laze the day away on the beautiful wraparound deck overlooking Barrett Cove, or spend some time swinging in the hammock, watching the swans glide by. This ...
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Nightly
€569 - €1,666 -
Weekly
€943 - €2,003 -
Monthly
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Also consider
Clearview, Easton
Nightly rate from
€569
€569
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 3, sleeps 7 |
| Bathrooms: | 3 |
A great little cottage with big amenities, Clearview is the answer to your getaway needs. Swimming pool, hot tub, fresh decorating and painting, and views ...
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Nightly
€569 - €1,553 -
Weekly
€910 - €1,856 -
Monthly
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Osprey Point, Easton
Nightly rate from
€631
€631
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 3, sleeps 8 |
| Bathrooms: | 3 |
This waterfront cottage has great cove views of Soltitude Creek, aptly named for the peace and serenity it delivers. Great waterviews with glass doors ...
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Nightly
€631 - €1,859 -
Weekly
€1,108 - €2,245 -
Monthly
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Harbor Hill, Easton
Nightly rate from
€384
€384
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 3, sleeps 8 |
| Bathrooms: | 3 |
As you drive down Main Street Oxford, one of Maryland's oldest and most charming ports of call, you begin to feel as if a John Phillip Sousa band should be ...
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Nightly
€384 - €908 -
Weekly
€646 - €1,083 -
Monthly
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Chesapeake Pines, Easton
Nightly rate from
€580
€580
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 4, sleeps 8 |
| Bathrooms: | 4 |
Full of unexpected touches, this unassuming one level home will suprise you as you settle in for your Eastern Shore Vacation. Top of the line remodeling, ...
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Nightly
€580 - €1,307 -
Weekly
€943 - €1,549 -
Monthly
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Pride and Joy Cottage, Easton
Nightly rate from
€498
€498
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 3, sleeps 6 |
| Bathrooms: | 2 |
Tucked away just as you arrive in the town of Oxford, Pride and Joy is a terrific spot for those looking for a step back in time--when you could walk to ...
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Nightly
€498 - €834 -
Weekly
€1,003 -
Monthly
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Also consider
Bayutiful, Easton
Nightly rate from
€363
€363
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 3, sleeps 6 |
| Bathrooms: | 1 |
A few miles past St. Michaels, a small unassuming cottage sits waiting to delight you with its ability to transport you to a different world, filled with ...
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Nightly
€363 - €868 -
Weekly
€616 - €1,036 -
Monthly
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St Michaels Waterfronts
www.EasternShoreVacations.com Vacation Rentals- Week or Weekends Premier Homes w/Pool - Search Now -
Vacation St Michaels
www.harbourtowne.com Waterfront Resort St.Michael's, MD. Conference, Golf & Wedding Packages -
Vacation Saint Michaels
www.FiveGables.com Romantic Inn & Spa with Luxurious Suites Near Chesapeake Bay, MD. -
#1 Site: Vacation Rentals
Rentalo.com/Vacation-Rental-Owners Advertise from $18/Month. High ROI Start Contacting Leads TODAY!
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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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