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Vacation Rentals (53)

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Featured listings
Blue Gates
Blue Gates
    Price: €1,272 - €2,710/night €2,470 - €3,269/week
  • Bedrooms: 4, sleeps 8
  • Bathrooms: 5
    • Contact Manager
Cod's Point
Cod's Point
    Price: €731 - €1,730/night €1,230 - €2,062/week
  • Bedrooms: 4, sleeps 12
  • Bathrooms: 4
    • Contact Manager
Cedar Point
Cedar Point
    Price: €588 - €1,667/night €1,014 - €2,008/week
  • Bedrooms: 3, sleeps 8
  • Bathrooms: 2
    • Contact Manager
Graceful View
Graceful View
    Price: €323 - €722/night €522 - €855/week
  • Bedrooms: 3, sleeps 6
  • Bathrooms: 2
    • Contact Manager
Caulk's Cove
Caulk's Cove
    Price: €486 - €1,078/night €875 - €1,291/week
  • Bedrooms: 4, sleeps 8
  • Bathrooms: 3
    • Contact Manager
My Blue Heron
My Blue Heron
    Price: €556 - €1,274/night €915 - €1,514/week
  • Bedrooms: 4, sleeps 8
  • Bathrooms: 3
    • Contact Manager
Macks Landing
Macks Landing
    Price: €546 - €1,306/night €884 - €1,553/week
  • Bedrooms: 3, sleeps 6
  • Bathrooms: 2
    • Contact Manager
Sunset Bay
Sunset Bay
    Price: €1,145 - €3,522/night €1,970 - €4,254/week
  • Bedrooms: 5, sleeps 16
  • Bathrooms: 3
    • Contact Manager
Pandion
Pandion
    Price: €544 - €1,209/night €903 - €1,435/week
  • Bedrooms: 3, sleeps 5
  • Bathrooms: 2
    • Contact Manager
Easton Hideaway
Easton Hideaway
    Price: €490 - €1,275/night €789 - €1,521/week
  • Bedrooms: 3, sleeps 6
  • Bathrooms: 2
    • Contact Manager

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Vacation rentals you can trust

[ Price / nt ] [ Price / wk ] [ Price / mo ] [ Bedrooms ]
The Strand
The Strand
Contact Manager
Nightly rate from
€383
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 ...
  • Nightly
    €383 - €972
  • Weekly
    €677 - €1,168
  • Monthly
    --
Lee Haven
Lee Haven
Contact Manager
Nightly rate from
€1,101
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 ...
  • Nightly
    €1,101 - €2,989
  • Weekly
    €1,927 - €3,598
  • Monthly
    --
Miles Aweigh
Miles Aweigh
Contact Manager
Nightly rate from
€628
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 ...
  • Nightly
    €628 - €1,668
  • Weekly
    €1,115 - €2,010
  • Monthly
    --
Pier Street
Pier Street
Contact Manager
Nightly rate from
€399
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 ...
  • Nightly
    €399 - €1,171
  • Weekly
    €998 - €1,464
  • Monthly
    --
Crabbiest Cottage
Crabbiest Cottage
Contact Manager
Nightly rate from
€472
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 ...
  • Nightly
    €472 - €1,065
  • Weekly
    €862 - €1,278
  • Monthly
    --
Mariner's Point
Mariner's Point
Contact Manager
Nightly rate from
€386
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 ...
  • Nightly
    €386 - €719
  • Weekly
    €685 - €852
  • Monthly
    --
Sycamore Acres
Sycamore Acres
Contact Manager
Nightly rate from
€1,188
Management: Professional
Property: Rental Home
Bedrooms: 6, sleeps 12
Bathrooms: 6
Linens & Towels Provided - Yes Beds Made upon Arrival - Yes Internet Access - DSL/Wireless Grill - Gas Privacy Rating 5* - **** Pet Friendly - No Central Air ...
  • Nightly
    €1,188 - €2,933
  • Weekly
    €2,163 - €3,532
  • Monthly
    --
Willows on the Miles
Willows on the Miles
Contact Manager
Nightly rate from
€1,071
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 ...
  • Nightly
    €1,071 - €2,959
  • Weekly
    €1,897 - €3,568
  • Monthly
    --
Hampden
Hampden
Contact Manager
Nightly rate from
€944
Management: Professional
Property: Rental Home
Bedrooms: 5, sleeps 10
Bathrooms: 5
The oldest existing brick house in Talbot County, Hampden awaits the history buff to discover all its secrets! Located on LaTrappe Creek, this 17th Century ...
  • Nightly
    €944 - €3,213
  • Weekly
    €1,732 - €3,912
  • Monthly
    --
Quarter Cove
Quarter Cove
Contact Manager
Nightly rate from
€620
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
    €620 - €1,843
  • Weekly
    €1,100 - €2,229
  • Monthly
    --
Hudson Manor
Hudson Manor
Contact Manager
Nightly rate from
€769
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 - ...
  • Nightly
    €769 - €2,166
  • Weekly
    €1,467 - €2,632
  • Monthly
    --
Captain's Cove
Captain's Cove
Contact Manager
Nightly rate from
€1,064
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 ...
  • Nightly
    €1,064 - €3,441
  • Weekly
    €1,889 - €4,173
  • Monthly
    --
Choptank Cottage
Choptank Cottage
Contact Manager
Nightly rate from
€451
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 ...
  • Nightly
    €451 - €878
  • Weekly
    €779 - €1,045
  • Monthly
    --
Swan Harbor
Swan Harbor
Contact Manager
Nightly rate from
€472
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 ...
  • Nightly
    €472 - €1,211
  • Weekly
    €842 - €1,457
  • Monthly
    --
Cabin Cove Manor
Cabin Cove Manor
Contact Manager
Nightly rate from
€748
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 ...
  • Nightly
    €748 - €2,208
  • Weekly
    €1,273 - €2,661
  • Monthly
    --
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