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Sort by: Type BR/BA/Sleeps Price

2 Kayaks to Meander Rivers Screened Porch 4 Alfresco Dinn...

Easton
2 Kayaks to Meander Rivers Screened Porch 4 Alfresco Dinners, Waterfront Pool The Swans Rest vacati...
Home 3 / 3 / 6

*
Online booking available

$509 - $616
Per Night

$1657 - $2270
Per Week

Estate Privacy Secs from St Mikes - Shoreline, Acreage, P...

St. Michaels
Estate Privacy Secs from St Mikes - Shoreline, Acreage, Pool, Decor, Hot Tub. Angel Cove Farm is th...
Home 6 / 6 / 12

*
Online booking available

$1225 - $1980
Per Night

$8264 - $10665
Per Week

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
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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

$772 - $964
Per Night

$2722 - $3978
Per Week

Blue Goose Cottage

Friendsville
Vouchers for nearby Lady Luck Casino. 2 Casino Vouchers for Lady Luck Casino (15 minutes away)for we...
Cottage 2 / 1 / 5

*
Online booking available

Contact
Owner
Directly
For Rates

Hot tub, wide water views, spectacular sunsets and unexpe...

Royal Oak
Hot tub, wide water views, spectacular sunsets and unexpected touches A taste of paradise on the Ch...
Home 4 / 4 / 8

*
Online booking available

$526 - $654
Per Night

$1696 - $2427
Per Week

Fern Run Cabin

Oakland
Absolute privacy! Hiking/Biking/dark nights. Wireless internet Outdoorsman's Dream. Miles of ATV...
Cabin 3 / 2 / 11

*
Online booking available

Contact
Owner
Directly
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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

$481 - $603
Per Night

$1560 - $2245
Per Week

Close in bungalow perfect landing spot for enjoying fall ...

Easton
Close in bungalow perfect landing spot for enjoying fall dining and festivals Private dock, newly f...
Cottage 3 / 2 / 6

*
Online booking available

$460 - $571
Per Night

$1549 - $2180
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

$480 - $606
Per Night

$1589 - $2305
Per Week

Shenandoah

Oakland
Large, Lakefont Luxury - every amenity. Relax in the Great Room or Rec Room taking in the panorami...
Home 5 / 4 / 14

*
Online booking available

Contact
Owner
Directly
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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

$811 - $1065
Per Night

$3342 - $4275
Per Week

Ideal fall getaway spot! Private island/sandbar, decks fr...

Church Creek
Ideal fall getaway spot! Private island/sandbar, decks from every Br! A world away from it all - Ho...
Cottage 4 / 3 / 8

*
Online booking available

$396 - $505
Per Night

$1280 - $1857
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

Red Run Cabin

Oakland
5 Minutes to Resort, Dock/Lake short walk. Relax at the picnic table, surrounded by evegreens and ...
Cabin 3 / 2 / 6

*
Online booking available

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Owner
Directly
For Rates

Duck Cove - A Crabbers Cottage Gone Upscale nestled in Ne...

Neavitt
Duck Cove - A Crabbers Cottage Gone Upscale nestled in Neavitt Village This little gem sits at the ...
Cottage 2 / 1 / 4

*
Online booking available

$342 - $506
Per Night

$1142 - $2032
Per Week

Chester River Getaway - All Seasons Fabulous - Kayaks, Vi...

Chestertown
Chester River Getaway - All Seasons Fabulous - Kayaks, Views, Pool, Fireplace What do we love the m...
Home 4 / 4 / 11

*
Online booking available

$513 - $970
Per Night

$1671 - $4528
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

$800 - $1317
Per Night

$4012 - $6787
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

$537 - $682
Per Night

$1860 - $2730
Per Week

Beautiful View

Mchenry
Timberlake is a spectacular 3 bedroom lakefront cottage that is ready to welcome your family year af...
Home 3 / 3 / 10

*
Online booking available

$297 - $621
Per Night

$1493 - $2447
Per Week

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

$415 - $528
Per Night

$1349 - $1958
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

$571 - $1059
Per Night

$1895 - $5252
Per Week

Glamping-Uzes

Oakland
If you like the idea of falling asleep under the stars and roasting marshmallows around a campfire, ...
Home 0 / 0 / 4

*
Online booking available

Contact
Owner
Directly
For Rates

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

$388 - $495
Per Night

$1248 - $2186
Per Week

Glamping-Delta

Oakland
If you like the idea of falling asleep under the stars and roasting marshmallows around a campfire, ...
Home 0 / 0 / 4

*
Online booking available

Contact
Owner
Directly
For Rates

 

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