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Sort by: Type BR/BA/Sleeps Price

Renovated Better than any Hgtv show - On a Waterfront Poi...

Royal Oak
Renovated Better than any Hgtv show - On a Waterfront Point of Land Perched on over 3 acres of wate...
Cottage 4 / 3 / 9

*
Online booking available

$630 - $1071
Per Night

$2455 - $4559
Per Week

Bear Crossing

Oakland
Absolute privacy! Hiking/Biking/dark nights. Wireless internet Outdoorsman's Dream. Miles of ATV...
Home 3 / 2 / 10

*
Online booking available

Contact
Owner
Directly
For Rates

Lovingly restored authentic 1920's waterman's cottage wit...

Tilghman Island
Lovingly restored authentic 1920's waterman's cottage with wide bay views This fantastic 1920's Wat...
Cottage 2 / 2 / 4

*
Online booking available

$333 - $474
Per Night

$1515 - $2095
Per Week

Prime Summer Weeks still Available! Canoe Included!

St. Michaels
Conveniently located between the charming towns of St Michaels and Easton, Osprey Point is just a st...
Home 3 / 2 / 8

*
Online booking available

$443 - $762
Per Night

$1985 - $3770
Per Week

Pool, hot tub, big water views - what more could you ask ...

Tilghman Island
Pool, hot tub, big water views - what more could you ask for in a cottage! A great little cottage w...
Cottage 3 / 3 / 7

*
Online booking available

$443 - $743
Per Night

$1905 - $3515
Per Week

Red Pine

Mchenry
Private setting, minutes to Lake. Private setting yet minutes to all Lake activities Minutes to WI...
Cabin 3 / 3 / 10

*
Online booking available

Contact
Owner
Directly
For Rates

New to the Market!

Oxford
Debating between staying in the village or on the water? Town Creek Haven provides the charm of in ...
Cottage 3 / 3 / 8

*
Online booking available

$455 - $655
Per Night

$1810 - $2597
Per Week

1900 Circa Quirky Cottage - Nothing Cookie Cutter About T...

Wittman
1900 Circa Quirky Cottage - Nothing Cookie Cutter About This One In Hawaiian, Kalohe means mischiev...
Cottage 3 / 3 / 5

*
Online booking available

$483 - $750
Per Night

$1810 - $3165
Per Week

Studio Condo Ocean Front

Ocean City
Studio Condo Ocean Front Unit Description: These well-appointed studios offer guests lovely pool vi...
Condo 0 / 1 / 4

*
Online booking available

$50 - $240
Per Night

$350 - $1680
Per Week

Animal Crossing

Swanton
Large, level yard. Very pet friendly, beach. Lake Access with beautiful BEACH. DOCK SLIP available f...
Home 4 / 3 / 8

*
Online booking available

Contact
Owner
Directly
For Rates

Memory Maker

Mchenry
Internet, Hot Tub, Firepit, 5 minutes to lake. 5 Minutes from Deep Creek Lake activities. Short d...
Home 3 / 2 / 5

*
Online booking available

Contact
Owner
Directly
For Rates

Blarney Stone Manor

Oakland
Rich log cabin in forest setting. Oversized Deck overlooking beautiful native stone landscaped area...
Home 3 / 4 / 6

*
Online booking available

Contact
Owner
Directly
For Rates

Deluxe 2 bedroom condo

Ocean City
Deluxe 2 bedroom condo Unit Description: This unit features a full kitchen, dining room, fireplace,...
Condo 2 / 2 / 6

*
Online booking available

$99 - $1175
Per Night

$693 - $8225
Per Week

Highest Guest Ratings - They love pool, wrap around decks...

Royal Oak
Highest Guest Ratings - They love pool, wrap around decks, cooks kitchen Outstanding vacation prope...
Home 6 / 5 / 12

*
Online booking available

$939 - $1544
Per Night

$4137 - $7123
Per Week

Steps from Oxford Beach... and Eastern Shore's Best Ice C...

Oxford
Steps from Oxford Beach... and Eastern Shore's Best Ice Cream! We call this 1900 circa cottage gem ...
Cottage 4 / 3 / 8

*
Online booking available

$416 - $598
Per Night

$2030 - $2255
Per Week

It's All Good

Swanton
Short walk to Lake and Deep Creek State Park. Across the street from Deep Creek Lake State Park. T...
Home 4 / 3 / 8

*
Online booking available

Contact
Owner
Directly
For Rates

Gracious waterfront home! Prime Summer Weeks Still Availa...

Neavitt
Gracious waterfront home! Prime Summer Weeks Still Available! Cheerfully decorated and water views ...
Home 5 / 3 / 9

*
Online booking available

$517 - $998
Per Night

$3087 - $5771
Per Week

3 bedroom 3 bath bayfront townhouse

Ocean City
3 bedroom 3 bath bayfront townhouse Unit Description: This two story, 3 bedroom, 3 bath townhouse o...
Condo 3 / 3 / 9

*
Online booking available

$89 - $454
Per Night

$623 - $3178
Per Week

One Bedroom Suite

Oxon Hill
One Bedroom Suite Unit Description: This luxuriously appointed Suite includes a full kitchen, a whi...
Room/ Suite 1 / 1 / 4

*
Online booking available

Contact
Owner
Directly
For Rates

La Lune

Swanton
So much quality, minutes to beach La Lune is creatively decorated with beautiful rugs , leather sofa...
Home 3 / 2 / 10

*
Online booking available

Contact
Owner
Directly
For Rates

Private cottage just one mile to St. Michaels. Great for ...

St. Michaels
Private cottage just one mile to St. Michaels. Great for kayaking and biking! Comfortably furnished...
Cottage 3 / 3 / 6

*
Online booking available

$455 - $647
Per Night

$2105 - $2890
Per Week

Friends & Family "Crash Pad" - Views, Pool, Kayaks, Bikes...

Neavitt
Friends & Family "Crash Pad" - Views, Pool, Kayaks, Bikes, Firepit & More Loblolly Cove is all abou...
Home 4 / 3 / 8

*
Online booking available

$521 - $878
Per Night

$2092 - $3897
Per Week

Deck on the Lake

Oakland
Relax on the enormous deck while taking in views of the lake. meander over the large yard to the wa...
Home 2 / 2 / 8

*
Online booking available

Contact
Owner
Directly
For Rates

Family friendly cottage near park and center of town. Ado...

Oxford
Family friendly cottage near park and center of town. Adorable! Tucked away just as you arrive in t...
Cottage 3 / 2 / 6

*
Online booking available

$400 - $548
Per Night

$1980 - $2205
Per Week

5 Acres, Kayaks, Pool, Cooks Kitchen, Screened Porch

Royal Oak
Active families will jump right in to The Cove House's many complimentary outdoor activities - kayak...
Home 5 / 5 / 12

*
Online booking available

$652 - $1318
Per Night

$3957 - $7948
Per Week

 

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