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Sort by: Type BR/BA/Sleeps Price

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

$444 - $551
Per Night

$1995 - $2330
Per Week

Every possible amenity for a dream family vacation and on...

St. Michaels
Every possible amenity for a dream family vacation and only 1/2 mile to town! Located on the outski...
Home 5 / 4 / 10

*
Online booking available

$860 - $1324
Per Night

$5756 - $6778
Per Week

Waterfront Point, Views from all sides, Love the Pool and...

Royal Oak
Waterfront Point, Views from all sides, Love the Pool and Kitchen Perched on over 3 acres of waterf...
Cottage 4 / 3 / 9

*
Online booking available

$596 - $1049
Per Night

$2275 - $4514
Per Week

Great central location w/pool, dock, hot tub & spacious l...

Easton
Great central location w/pool, dock, hot tub & spacious light filled kitchen. This charming cottage...
Home 4 / 4 / 8

*
Online booking available

$629 - $975
Per Night

$2407 - $4372
Per Week

Beautiful Historic Home Just Minutes from Oxford

Oxford
Nestled along the prestigious Oxford Road corridor is a splendid estate home reminiscent of Martha S...
Home 6 / 6 / 12

*
Online booking available

$890 - $1425
Per Night

$3537 - $6497
Per Week

Wide Open Spaces, Clear Nights, Crabbers Dock, Waterside ...

Cambridge
Wide Open Spaces, Clear Nights, Crabbers Dock, Waterside Pool - Kids Love It Think back to a childh...
Home 5 / 5 / 18

*
Online booking available

$711 - $1412
Per Night

$3760 - $7099
Per Week

Quaint renovated 1910 hideaway - Guests Love Waterfront S...

Bozman
Quaint renovated 1910 hideaway - Guests Love Waterfront Screened Porch This quaint cottage packs a ...
Cottage 3 / 2 / 6

*
Online booking available

$515 - $795
Per Night

$2000 - $3565
Per Week

Private hideaway just a 1/2 mile from historic district. ...

St. Michaels
Private hideaway just a 1/2 mile from historic district. Great for biking. Comfortably furnished, s...
Cottage 3 / 3 / 6

*
Online booking available

$536 - $664
Per Night

$2155 - $2840
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

$515 - $772
Per Night

$1955 - $3440
Per Week

Darling in town cottage with private sandy beach, dock, C...

Oxford
Darling in town cottage with private sandy beach, dock, Comb for Seaglass! Looking for a beach? Yo...
Cottage 3 / 2 / 6

*
Online booking available

$418 - $498
Per Night

$1580 - $2255
Per Week

Luxury estate property with pool, boathouse, 4 en suite BRs.

Easton
Elegantly furnished and located in a prestigious estate area of Talbot County, Blue Gates offers a c...
Home 4 / 4 / 10

*
Online booking available

$785 - $1269
Per Night

$3102 - $5771
Per Week

Welcome to Paradise

Mchenry
High Amenity Value - read on. 5 Minutes from Deep Creek Lake activities. Short distance to Wisp S...
Home 3 / 2 / 8

*
Online booking available

Contact
Owner
Directly
For Rates

Historic, Renovated, Darling, Love the Front Porch -Walk ...

Oxford
Historic, Renovated, Darling, Love the Front Porch -Walk to Everything Oxford Resting underneath th...
Cottage 2 / 2 / 4

*
Online booking available

$348 - $432
Per Night

$1525 - $1795
Per Week

Perfect for capturing last family memories--plenty of spa...

Cambridge
Perfect for capturing last family memories--plenty of space and things to do! Hudson Manor is fabul...
Home 7 / 6 / 22

*
Online booking available

$974 - $1578
Per Night

$4042 - $7674
Per Week

All Seasons

Oakland
Affordable Lake Access/Dock - modest home. Private dock slip with nice setting and spectacular view...
Home 4 / 3 / 9

*
Online booking available

Contact
Owner
Directly
For Rates

Bay Breezes Stream Through Home - Light Filled, Elegant O...

Sherwood
Bay Breezes Stream Through Home - Light Filled, Elegant Outdoor Living Spaces The home boasts 2,800...
Home 3 / 4 / 6

*
Online booking available

$733 - $1051
Per Night

$2855 - $4587
Per Week

It's all about the view! Decks, shaded back yard, hot tub...

Tilghman Island
It's all about the view! Decks, shaded back yard, hot tub, Sunsets Known as the "Pearl of the Chesa...
Home 3 / 3 / 6

*
Online booking available

$566 - $658
Per Night

$2015 - $2595
Per Week

Beautiful Lakefront Home w/Private Pool and Dock Slip

Oakland
Come and stay at Deep Creek's premier deluxe lakefront property where dreams do come true, and the c...
Home 8 / 8 / 26

*
Online booking available

$1436 - $2401
Per Night

$5864 - $9266
Per Week

Centrally located historic cottage with screened porch an...

Oxford
Centrally located historic cottage with screened porch and patio garden We love this cottage for ma...
Cottage 4 / 3 / 8

*
Online booking available

$457 - $564
Per Night

$2020 - $2355
Per Week

Great spot for boating, crabbing and views from every room.

Cambridge
Situated on over 25 acres, we love this home's privacy with the beautiful waterside pool. The farmho...
Home 4 / 4 / 10

*
Online booking available

$686 - $1063
Per Night

$2522 - $4557
Per Week

Close in cottage with pool/hot tub. Great for sightseeing...

Easton
Close in cottage with pool/hot tub. Great for sightseeing or fall festivals This darling well kept ...
Cottage 3 / 2 / 6

*
Online booking available

$529 - $749
Per Night

$2275 - $3260
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

Deep Creek Village 31

Mchenry
Walk to ski slopes, Lake out back. Deep Creek Lake Rental: 4-Level Townhouse directly across from ...
Home 3 / 3 / 8

*
Online booking available

Contact
Owner
Directly
For Rates

Studio Condo Street View

Ocean City
Studio Condo Street View Unit Description: These well-appointed studios offer guests lovely views, ...
Condo 0 / 1 / 4

*
Online booking available

$50 - $999
Per Night

$350 - $6993
Per Week

Single family cottage with pool, kayaks, play gym & dock

Wittman
This charming property located just outside of St. Michaels has all you need for plug-n-play fun for...
Cottage 3 / 2 / 6

*
Online booking available

$496 - $681
Per Night

$1760 - $2965
Per Week

 

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