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Results: 234 Rentals

  • Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock
    From $1191 per night (USD)

    VRBO

    Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    10

    A breathtaking waterfront estate that seamlessly combines luxury and nature. Welcome to Miles End, a breathtaking water ...

    From $1191 per night (USD)

    VRBO

    Details
  • Charming 1-bedroom cottage on the water, minutes from St Michaels MD
    From $188 per night (USD)

    VRBO

    Charming 1-bedroom cottage on the water, minutes from St Michaels MD

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    King Size Comfort. The ambience of each cottage is one of relaxed comfort. Fashionable cottage décor is enhanced with co ...

    From $188 per night (USD)

    VRBO

    Details
  • Waterfront cottage, 1 bd 1 bath, Perfect for your next getaway!
    From $247 per night (USD)

    VRBO

    Waterfront cottage, 1 bd 1 bath, Perfect for your next getaway!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The perfect couples’ getaway. The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhan ...

    From $247 per night (USD)

    VRBO

    Details
  • Charming 2-bedroom cottage, waterfront, WiFi
    From $227 per night (USD)

    VRBO

    Charming 2-bedroom cottage, waterfront, WiFi

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    The perfect, small family, getaway. The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is ...

    From $227 per night (USD)

    VRBO

    Details
  • Stunning Chesapeake Waterfront Home
    From $770 per night (USD)

    VRBO

    Stunning Chesapeake Waterfront Home

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Spectacular new waterfront home in beautiful historic Oxford, comfortably sleeps 10 with perfect set up for 2 families. ...

    From $770 per night (USD)

    VRBO

    Details
  • The Farm House at Hunting Creek
    From $445 per night (USD)

    Expedia

    The Farm House at Hunting Creek

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    Experience the charm of this stunning, gated estate carriage house, nestled on 80 acres of breathtaking land. With panor ...

    From $445 per night (USD)

    Expedia

    Details
  • Walk to Dtwn: Waterfront Eastern Shore Townhome!
    From $335 per night (USD)

    VRBO

    Walk to Dtwn: Waterfront Eastern Shore Townhome!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Game Room | Scenic Waterfront Deck | Community Pool | Pet Friendly w/ Fee | EV Charger Experience life in the heart of ...

    From $335 per night (USD)

    VRBO

    Details
  • Waterfront Home with Pool & Pet Friendly
    From $844 per night (USD)

    Expedia

    Waterfront Home with Pool & Pet Friendly

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Wake up to waterfront living - toss crab pot off the dock in the morning & steam your catch for dinner. Spend a ...

    From $844 per night (USD)

    Expedia

    Details
  • Spacious Family Getaway – Summer Ready!
    Click For Pricing

    VRBO

    Spacious Family Getaway – Summer Ready!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    6

    Summary: Pack your bags and gather the crew—this bright and welcoming 4-bedroom, 4.5-bath home is everything a summer ge ...

    Click For Pricing

    VRBO

    Details
  • Minutes from Downtown St. Michaels | Pool | Dock
    From $1003 per night (USD)

    Expedia

    Minutes from Downtown St. Michaels | Pool | Dock

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Location , Location, Location Escape to this stunning cedar Lindal home on the Eastern Shore, just a short drive from h ...

    From $1003 per night (USD)

    Expedia

    Details
  • Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
    From $102 per night (USD)

    VRBO

    Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Wye Mills is waiting for you at this awesome 1-bedroom cottage. With WiFi, heating, a washing machine, and more, guests ...

    From $102 per night (USD)

    VRBO

    Details
  • Cottage #4 Chesapeake Blue  down the drive way.
    From $294 per night (USD)

    VRBO

    Cottage #4 Chesapeake Blue down the drive way.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to our beautiful waterfront property, open for guests from March 25th to November 1st. We have a minimum stay of ...

    From $294 per night (USD)

    VRBO

    Details
  • #3 Mallard Cottage  (located 3rd down drive)
    From $294 per night (USD)

    VRBO

    #3 Mallard Cottage (located 3rd down drive)

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to our beautiful waterfront property, open for guests from March 25th to November 1st. We have a minimum stay of ...

    From $294 per night (USD)

    VRBO

    Details
  • Charming 3 Bedroom Cottage – 6 Miles to St. Michaels
    From $222 per night (USD)

    Expedia

    Charming 3 Bedroom Cottage – 6 Miles to St. Michaels

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Welcome to Pot Pie Cottage — your charming, well-priced escape just minutes from the historic town of St. Micha ...

    From $222 per night (USD)

    Expedia

    Details
  • Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
    From $1114 per night (USD)

    VRBO

    Minutes from Downtown Easton and St. Michaels | Pool | Private Dock

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    9

    Take control of your next vacation. Escape to your dream waterfront vacation at this extraordinary 5-bedroom estate on ...

    From $1114 per night (USD)

    VRBO

    Details
  • Aurora Blue - A Stylish Experience \n
    From $269 per night (USD)

    VRBO

    Aurora Blue - A Stylish Experience \n

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Stylish experience at the centrally located retreat. New owners purchased East and renovated the entire home both inside ...

    From $269 per night (USD)

    VRBO

    Details
  • Charming, Waterfront 2-bedroom house Royal Oak
    From $560 per night (USD)

    VRBO

    Charming, Waterfront 2-bedroom house Royal Oak

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Your cozy getaway awaits in Royal Oak at this brilliant house. With 2 bedrooms guests can unwind in comfort. The proper ...

    From $560 per night (USD)

    VRBO

    Details
  • Downtown Oxford | Private Beach | Private Pool | Luxury
    From $980 per night (USD)

    Expedia

    Downtown Oxford | Private Beach | Private Pool | Luxury

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Luxury awaits at The Beach House, a stunning 4-bedroom, 4.5-bathroom vacation extravaganza in the vibrant Oxford neighbo ...

    From $980 per night (USD)

    Expedia

    Details
  • Secluded 1870s farmhouse full of historic charm + breathtaking waterfront views!
    From $880 per night (USD)

    VRBO

    Secluded 1870s farmhouse full of historic charm + breathtaking waterfront views!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    This secluded 1870s farmhouse is full of historic charm and surrounded by natural beauty. Take in breathtaking views of ...

    From $880 per night (USD)

    VRBO

    Details
  • 3 Bedroom St. Michaels Retreat | Walk to town
    From $364 per night (USD)

    Expedia

    3 Bedroom St. Michaels Retreat | Walk to town

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Easy walking and biking distance to the heart of St. Michaels. Enjoy shops, restaurants, and waterfront charm j ...

    From $364 per night (USD)

    Expedia

    Details
  • Charming 3-bedroom  in Village of Claiborne \nBOOK 3 NIGHTS GET 4TH FREE STR24-33
    From $346 per night (USD)

    VRBO

    Charming 3-bedroom in Village of Claiborne \nBOOK 3 NIGHTS GET 4TH FREE STR24-33

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Discover the beauty of Claiborne and feel the calm from this 3-bedroom house. With 2 queen beds, 1 full bed, and 1 twin ...

    From $346 per night (USD)

    VRBO

    Details
  • Waterfront Farmhouse | Pool, Dock, Pets Welcome
    Click For Pricing

    Expedia

    Waterfront Farmhouse | Pool, Dock, Pets Welcome

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Imagine waking up to the gentle lapping of water on a quiet inlet, just a short drive from the charming streets ...

    Click For Pricing

    Expedia

    Details
  • #2 Egret Cottage Harris Cove
    From $294 per night (USD)

    VRBO

    #2 Egret Cottage Harris Cove

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Relax with the whole family at this peaceful place to stay. Great Sunset and Sunrises, located on Harris Creek, each cot ...

    From $294 per night (USD)

    VRBO

    Details
  • Cottage #5 White Swan At Water with Deck
    From $315 per night (USD)

    VRBO

    Cottage #5 White Swan At Water with Deck

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to our beautiful waterfront property, open for guests from March 25th to November 1st. We have a minimum stay of ...

    From $315 per night (USD)

    VRBO

    Details
  • Cottage #8 Herons Nest Lg 2 rooms Under Main House
    From $348 per night (USD)

    VRBO

    Cottage #8 Herons Nest Lg 2 rooms Under Main House

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Welcome to our beautiful waterfront property, open for guests from March 25th to November 1st. We have a minimum stay of ...

    From $348 per night (USD)

    VRBO

    Details
  • 3Br/1Ba Pondview Langsdale House - A Historic Stay with Heart
    From $366 per night (USD)

    VRBO

    3Br/1Ba Pondview Langsdale House - A Historic Stay with Heart

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    The Pondview Langsdale House – A Historic Stay with Heart Step into a piece of Easton’s rich history at The Pondview Lan ...

    From $366 per night (USD)

    VRBO

    Details
  • Downtown Oxford | Character Filled
    From $454 per night (USD)

    VRBO

    Downtown Oxford | Character Filled

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Ahoy there, mateys! Prepare to be captivated by this newly renovated 3-bedroom, 2-bathroom vacation rental in Oxford, ...

    From $454 per night (USD)

    VRBO

    Details
  • Brand-New Pool! Waterfront Bozman Village Home
    From $339 per night (USD)

    Expedia

    Brand-New Pool! Waterfront Bozman Village Home

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Pets Welcome w/ Fee | 5 Mi to St. Michaels | Go Kayaking Experience classic Eastern Shore living at this 4-bedroom, 2.5 ...

    From $339 per night (USD)

    Expedia

    Details
  • Beautiful 3-bedroom Miles River waterfront in tranquil Easton - Relax and unwind
    From $676 per night (USD)

    VRBO

    Beautiful 3-bedroom Miles River waterfront in tranquil Easton - Relax and unwind

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Unwind in Easton at this beautiful newly refreshed waterfront home nestled in private cove on 47 acres of river and farm ...

    From $676 per night (USD)

    VRBO

    Details
  • Minutes from Downtown St. Michaels | Character Filled
    From $391 per night (USD)

    Expedia

    Minutes from Downtown St. Michaels | Character Filled

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    TGIF … Escape to happiness, laughter, and unforgettable moments at The Weekender! This bright and airy 2-bedroom, 2.5- ...

    From $391 per night (USD)

    Expedia

    Details
  • Walk to Park & River: Dog-Friendly Cambridge Gem
    From $180 per night (USD)

    VRBO

    Walk to Park & River: Dog-Friendly Cambridge Gem

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Half-Mi to Historic Downtown | Covered Porch | Yard Space | Great Fishing Area Whether you’re here to explore Cambridge ...

    From $180 per night (USD)

    VRBO

    Details
  • Walk to Waterfront • Cozy Oxford Cottage
    From $402 per night (USD)

    Expedia

    Walk to Waterfront • Cozy Oxford Cottage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Discover the charm of Maryland’s Eastern Shore at our cozy cottage nestled in the heart of Oxford. Just steps f ...

    From $402 per night (USD)

    Expedia

    Details
  • Waterfront Paradise | Pool, Views & Serenity
    From $979 per night (USD)

    VRBO

    Waterfront Paradise | Pool, Views & Serenity

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Gather your favorite people and escape to a spacious waterfront haven in Royal Oak. From coffee at sunrise on ...

    From $979 per night (USD)

    VRBO

    Details
  • Waterfront Retreat wth Pool | Perfect for Late Summer & Fall Getaways
    From $2146 per night (USD)

    Expedia

    Waterfront Retreat wth Pool | Perfect for Late Summer & Fall Getaways

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Summary: End your summer in style and welcome fall on Maryland’s Eastern Shore. At Eventide Farm, the seasons unfold bea ...

    From $2146 per night (USD)

    Expedia

    Details