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Results: 241 Rentals

  • Stunning Waterfront Escape with New Pool
    From $912 per night (USD)

    VRBO

    Stunning Waterfront Escape with New Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Whether you're looking to relax poolside or explore the surrounding area, this waterfront home has everything y ...

    From $912 per night (USD)

    VRBO

    Details
  • St Michaels Retreat, Log Cabin, Family & Pet-Friendly
    From $751 per night (USD)

    VRBO

    St Michaels Retreat, Log Cabin, Family & Pet-Friendly

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    4th of July Availability!! If you enjoy the old-fashioned fireworks, ice cream and BBQ picnic- Independence day celebra ...

    From $751 per night (USD)

    VRBO

    Details
  • Time Stands Still At the Dock.
    From $553 per night (USD)

    VRBO

    Time Stands Still At the Dock.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Minutes from St Michaels, this peaceful retreat will have guests never wanting to leave. Panoramic views of the ...

    From $553 per night (USD)

    VRBO

    Details
  • Downtown Oxford | Outdoor Dining | Character Filled
    From $412 per night (USD)

    Expedia

    Downtown Oxford | Outdoor Dining | Character Filled

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Old School Charm Meets New School Living! This charming 3BR, 2BA duplex vacation home within walking distance from Down ...

    From $412 per night (USD)

    Expedia

    Details
  • Minutes from Downtown Easton and St. Michaels | Pool
    From $1397 per night (USD)

    VRBO

    Minutes from Downtown Easton and St. Michaels | Pool

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Welcome to your dream retreat, nestled in a serene cove that feels like a page from a fairytale. This enchanting waterfr ...

    From $1397 per night (USD)

    VRBO

    Details
  • Short drive to Downtown Cambridge | Private Dock | Guest House
    From $1156 per night (USD)

    Expedia

    Short drive to Downtown Cambridge | Private Dock | Guest House

    Bedrooms:
    3
    Bathrooms:
    7
    Sleeps:
    14

    Bucolic and Serene NEW POOL COMING SOON! This charming 6BR, 3BA Victorian waterfront vacation home complimented by a 1B ...

    From $1156 per night (USD)

    Expedia

    Details
  • Charming Waterfront Cottage Retreat near St. Michaels
    From $394 per night (USD)

    VRBO

    Charming Waterfront Cottage Retreat near St. Michaels

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover the ultimate getaway at this stunning waterfront cottage on Maryland’s picturesque Eastern Shore, nestled minut ...

    From $394 per night (USD)

    VRBO

    Details
  • Charming 1-bedroom cottage in downtown Saint Michaels
    Click For Pricing

    Expedia

    Charming 1-bedroom cottage in downtown Saint Michaels

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Stay comfortably in Saint Michaels at this 1-bedroom cottage. Nestled in a beautiful and peaceful setting, this brillian ...

    Click For Pricing

    Expedia

    Details
  • Cambridge Apt in Walkable Neighborhood
    From $157 per night (USD)

    VRBO

    Cambridge Apt in Walkable Neighborhood

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Waterfront Setting | Close to Local Eats Explore the quiet side of the Chesapeake Bay with your closest travel buddy at ...

    From $157 per night (USD)

    VRBO

    Details
  • Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock
    From $1063 per night (USD)

    Expedia

    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 $1063 per night (USD)

    Expedia

    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 $245 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 $245 per night (USD)

    VRBO

    Details
  • Charming 2-bedroom cottage, waterfront, WiFi
    From $277 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 $277 per night (USD)

    VRBO

    Details
  • Stunning Chesapeake Waterfront Home
    From $972 per night (USD)

    Expedia

    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 $972 per night (USD)

    Expedia

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

    VRBO

    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)

    VRBO

    Details
  • Walk to Dtwn: Waterfront Eastern Shore Townhome!
    From $419 per night (USD)

    Expedia

    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 $419 per night (USD)

    Expedia

    Details
  • Waterfront Home with Pool & Pet Friendly
    From $964 per night (USD)

    VRBO

    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 $964 per night (USD)

    VRBO

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

    Expedia

    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

    Expedia

    Details
  • Cottage #1 Lighthouse First Cottage down driveway
    From $276 per night (USD)

    VRBO

    Cottage #1 Lighthouse First Cottage down driveway

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    OPEN March 25th until October 31st each year. No 1 is First cottage down drive has a full Kitchen, dining table, queen s ...

    From $276 per night (USD)

    VRBO

    Details
  • Minutes from Downtown St. Michaels | Pool | Dock
    From $780 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 $780 per night (USD)

    Expedia

    Details
  • Escape to The Beach House - Your Waterfront Oasis Awaits!
    From $1096 per night (USD)

    VRBO

    Escape to The Beach House - Your Waterfront Oasis Awaits!

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    Discover paradise at The Beach House, a stunning waterfront rental offered by Tidewater Vacations. Nestled along the ser ...

    From $1096 per night (USD)

    VRBO

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

    Expedia

    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)

    Expedia

    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
  • Cottage #9 Stateroom located under main home
    From $236 per night (USD)

    VRBO

    Cottage #9 Stateroom located under main home

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    OPEN March 25th to Nov 1st. Each year. State Room has no kitchen is located under main house, consist of small dining ta ...

    From $236 per night (USD)

    VRBO

    Details
  • Cottage #6 Wild Goose on the left of Main House
    From $319 per night (USD)

    Expedia

    Cottage #6 Wild Goose on the left of Main House

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    OPEN March 25th to Nov 1st. No6) Wild goose located to left of main house, consist of full Kitchen, dining table, queen ...

    From $319 per night (USD)

    Expedia

    Details
  • Charming Well Priced Home Minutes From St Michaels
    From $251 per night (USD)

    VRBO

    Charming Well Priced Home Minutes From St Michaels

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Traveling to the shore for a friends & family event? Looking for a cozy well priced option? Centrally located b ...

    From $251 per night (USD)

    VRBO

    Details
  • Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
    From $1289 per night (USD)

    Expedia

    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 $1289 per night (USD)

    Expedia

    Details
  • Aurora Blue - A Stylish Experience \n
    From $393 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 $393 per night (USD)

    VRBO

    Details
  • Charming, Waterfront 2-bedroom house Royal Oak
    From $578 per night (USD)

    Expedia

    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 $578 per night (USD)

    Expedia

    Details
  • Downtown Oxford | Private Beach | Private Pool | Luxury
    From $978 per night (USD)

    VRBO

    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 $978 per night (USD)

    VRBO

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

    Expedia

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

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

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

    From $880 per night (USD)

    Expedia

    Details
  • St. Michaels Escape – Walk to Town!
    From $377 per night (USD)

    VRBO

    St. Michaels Escape – 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 $377 per night (USD)

    VRBO

    Details
  • Charming 3-bedroom  in Village of Claiborne \nwith continental breakfast STR24-33
    From $346 per night (USD)

    Expedia

    Charming 3-bedroom in Village of Claiborne \nwith continental breakfast 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)

    Expedia

    Details
  • Waterfront Farmhouse | Pool, Dock, Pets Welcome
    From $1261 per night (USD)

    VRBO

    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 ...

    From $1261 per night (USD)

    VRBO

    Details
  • #2 Egret Cottage Harris Cove
    From $384 per night (USD)

    Expedia

    #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 $384 per night (USD)

    Expedia

    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 $371 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 $371 per night (USD)

    VRBO

    Details
  • 3Br/1Ba Pondview Langsdale House - A Historic Stay with Heart
    From $404 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 $404 per night (USD)

    VRBO

    Details
  • Downtown Oxford | Character Filled
    From $469 per night (USD)

    Expedia

    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 $469 per night (USD)

    Expedia

    Details
  • Waterfront Home w/ Hot Tub in Bozman Village!
    From $340 per night (USD)

    VRBO

    Waterfront Home w/ Hot Tub in Bozman Village!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

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

    From $340 per night (USD)

    VRBO

    Details