Maryland Vacation Rental Getaways

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  • Property Options
  • Amenities
  • Location Type
  • Bed
  • Bath
  • Sleeps
Max Price Per Week $
  • Special Offers
  • Online Booking
  • Home/Villa
  • Cottage/Cabin
  • Condo/Townhome
  • Bed & Breakfast
  • Apt/Room/Suite
  • Air Conditioning
  • Washer/Dryer
  • Full Kitchen
  • Satellite/Cable TV
  • Handicap Access
  • High Speed Internet
  • Elevator
  • Maid Service
  • Garage Parking
  • Pets Allowed
  • Private Pool
  • Pool Access
  • Hot Tub
  • Fireplace
  • Smoking allowed
  • Beach Access
  • Beach Front
  • Golf on site
  • Golf nearby
  • Ocean Front
  • Ocean View
  • Lake Front
  • Lake View
  • Ski in/out
  • Walk to Slopes
  • Skiing nearby
 
Sort by: Type BR/BA/Sleeps Price

2 bed/2 bath condo

Ocean City
2 bed/2 bath condo Unit Description: Our units include a Jacuzzi bathtub, a fully equipped kitchen,...
Condo 2 / 2 / 6

*
Online booking available

$69 - $249
Per Night

$483 - $1743
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

$414 - $498
Per Night

$1525 - $1857
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

$536 - $970
Per Night

$1995 - $4118
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

$399 - $491
Per Night

$1565 - $1902
Per Week

Brand new fabulous outdoor kitchen and pizza oven, grill ...

St. Michaels
Brand new fabulous outdoor kitchen and pizza oven, grill and smoker! One of our most popular houses...
Cottage 3 / 3 / 6

*
Online booking available

$571 - $893
Per Night

$2200 - $3791
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

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

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

$524 - $664
Per Night

$2060 - $2583
Per Week

Steps from Pier, Shoreline & Pool - Simple Country Living...

Cambridge
Steps from Pier, Shoreline & Pool - Simple Country Living on 25 Acres Bring your gear - on over 25 ...
Home 5 / 5 / 13

*
Online booking available

$630 - $1006
Per Night

$2520 - $4377
Per Week

Swallow Hollow

Oakland
Minutes to Swallow Falls, Deep Creek Lake. Great central location 3 minutes from Swallow Falls St...
Cottage 2 / 2 / 10

*
Online booking available

Contact
Owner
Directly
For Rates

Guests Tell Us One of The Best Crabbing Docks Around, Sim...

Bozman
Guests Tell Us One of The Best Crabbing Docks Around, Simple Waterfront At the end of this meanderi...
Cottage 3 / 2 / 6

*
Online booking available

$258 - $396
Per Night

$1195 - $1538
Per Week

Tucked Away - Big Sky, Privacy & Enormous Acreage - All t...

Taylors Island
Tucked Away - Big Sky, Privacy & Enormous Acreage - All to yourself Located at the end of the road ...
Room/ Suite 5 / 5 / 14

*
Online booking available

$568 - $802
Per Night

$3548 - $4990
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

$565 - $903
Per Night

$2255 - $3890
Per Week

Closest 4 Br vacation home to St Mikes with big St. Micha...

St. Michaels
Closest 4 Br vacation home to St Mikes with big St. Michaels Harbor views. A sprawling one level ho...
Home 4 / 3 / 8

*
Online booking available

$324 - $478
Per Night

$1345 - $1862
Per Week

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

Fabulous Fall Cottage Getaway! Enjoy cozy views and Inn n...

Oxford
Fabulous Fall Cottage Getaway! Enjoy cozy views and Inn next door. This charming Sears Cottage is l...
Cottage 2 / 1 / 4

*
Online booking available

$201 - $351
Per Night

$1017 - $1913
Per Week

An Unforgettable Home; 2 Hot Tubs, Private Indoor Pool, 2...

Swanton
An Unforgettable Home; 2 Hot Tubs, Private Indoor Pool, 2 Dock Slips & More!! Welcome family and fr...
Home 8 / 9 / 26

*
Online booking available

$1401 - $2170
Per Night

$5892 - $9687
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

$434 - $673
Per Night

$1565 - $2696
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! Who says vacations are only for summ...
Cottage 4 / 3 / 8

*
Online booking available

$420 - $648
Per Night

$1660 - $2382
Per Week

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

$320 - $479
Per Night

$1284 - $1832
Per Week

Waterfront Home with Pool near St Michaels and Easton

Easton
Enjoy your vacation at this expansive beautifully furnished updated home with private pool, dock and...
Cottage 4 / 3 / 8

*
Online booking available

$2010 - $3486
Per Week

Perched Between Oxford and Easton - Fab Views and Location

Easton
Perfectly located between Oxford and Easton - Gladimere is nestled on 3 1/2 acres of private waterf...
Cottage 3 / 3 / 6

*
Online booking available

$515 - $750
Per Night

$1930 - $3220
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

$721 - $1146
Per Night

$2954 - $5083
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

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

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

*
Online booking available

$459 - $698
Per Night

$1615 - $2746
Per Week

 

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