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Maryland Skiing Vacation Rentals

68 Maryland Skiing Vacation Rentals were found matching your criteria. These vacation rentals are presented by their owners or managers. Please click on the photos or links below, then contact them directly with your inquiries. Use the search criteria box on the left of the page to refine your search within Maryland, United States.
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Listings 1 - 25 of 68
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5 bedroom Vacation Rental Home in Oakland
Home: 5 Bedroom, 4 Bathroom, Sleeps 13
Location: Oakland, Maryland, United States
Description: Highest quality at every turn. Quality chalet in a forest setting 3 minutes from Swallow Falls State Park with Maryland's highest waterfall 5 mi... Learn More
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4 bedroom Vacation Rental Home in Oakland
Home: 4 Bedroom, 4 Bathroom, Sleeps 12
Location: Oakland, Maryland, United States
Description: Memory Lane got its name from the gracious, huge trees and beautifully maintained lawn which give you the comfort of home with all the amenities of... Learn More
Rates
$347 - $522 night
$1493 - $2122 week


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3 bedroom Vacation Rental Cabin in Oakland
Cabin: 3 Bedroom, 2 Bathroom, Sleeps 11
Location: Oakland, Maryland, United States
Description: Absolute privacy! Hiking/Biking/dark nights. Wireless internet Outdoorsman's Dream. Miles of ATV roads & trails at nearby Snaggy Mountain State... Learn More
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4 bedroom Vacation Rental Cottage in Mcdaniel
Cottage: 4 Bedroom, 3 Bathroom, Sleeps 8
Location: Mcdaniel, Maryland, United States
Description: Tucked Away - Guests Love Waterfront Screen Porch & Sunning on Dock We love this cottage for what it is not - it isn't busy, cluttered or noisy. M... Learn More
Rates
$481 - $554 night
$1766 - $2230 week


Pet Friendly   Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Home in Oakland
Home: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Oakland, Maryland, United States
Description: 5 Minutes to Resort, Dock/Lake short walk. Private dock slip with nice park-like setting Nestled in towering pines, feeling of privacy Minutes fr... Learn More
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2 bedroom Vacation Rental Home in Oakland
Home: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Oakland, Maryland, United States
Description: Forest out back, Centrally located. Centrally located 2 BR, 2BA towhome Work on the WIFI before exploring the nearby Resort Area Quite, dead end ... Learn More
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3 bedroom Vacation Rental Home in Oakland
Home: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: Oakland, Maryland, United States
Description: Tucked in evergreens. Enormous wood-burning fireplace. Nestled on a lovely wooded lot, this 3 bedroom, 2 bath home features a spacious family roo... Learn More
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2 bedroom Vacation Rental Cottage in Neavitt
Cottage: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Neavitt, Maryland, United States
Description: Duck Cove - A Crabbers Cottage Gone Upscale nestled in Neavitt Village This little gem sits at the end of Duck Cove Lane in heart of Neavitt Villa... Learn More
Rates
$342 - $539 night
$1348 - $2160 week


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5 bedroom Vacation Rental Home in Cambridge
Home: 5 Bedroom, 5 Bathroom, Sleeps 18
Location: Cambridge, Maryland, United States
Description: Wide Open Spaces, Clear Nights, Crabbers Dock, Waterside Pool - Kids Love It Think back to a childhood vacation with your aunts, uncles, grandpare... Learn More
Rates
$644 - $914 night
$3357 - $4320 week


Pet Friendly   Non Smoking   Swimming Pool


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3 bedroom Vacation Rental Home in Oakland
Home: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Oakland, Maryland, United States
Description: 350 Acres! River Access, 12 min to Resort. Conveniently located near Swallow Falls & Herrington Manor State Parks. Relax on the screened porch in... Learn More
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Studio Vacation Rental Home in Oakland
Home: Studio, 0 Bathroom, Sleeps 4
Location: Oakland, Maryland, United States
Description: If you like the idea of falling asleep under the stars and roasting marshmallows around a campfire, but the hassles of pitching a tent and sleeping... Learn More
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4 bedroom Vacation Rental Home in Trappe
Home: 4 Bedroom, 3 Bathroom, Sleeps 8
Location: Trappe, Maryland, United States
Description: Spacious and private--sleeps up to 12! Less than weekly stays available! A wonderful getaway spot for a multi-family group, Cod's Point is a spaci... Learn More
Rates
$510 - $632 night
$2025 - $2705 week


Pet Friendly   Non Smoking   High-Speed Internet


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Studio Vacation Rental Home in Oakland
Home: Studio, 0 Bathroom, Sleeps 4
Location: Oakland, Maryland, United States
Description: If you like the idea of falling asleep under the stars and roasting marshmallows around a campfire, but the hassles of pitching a tent and sleeping... Learn More
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Pet Friendly   Non Smoking   High-Speed Internet


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5 bedroom Vacation Rental Home in Mchenry
Home: 5 Bedroom, 3 Bathroom, Sleeps 11
Location: Mchenry, Maryland, United States
Description: Steps from WISP. TEST DRIVE before you buy - house is 'For Sale'! Walking distance to the base of the ski slopes Enjoy the mountain coaster, pain... Learn More
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3 bedroom Vacation Rental Home in Mchenry
Home: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Mchenry, Maryland, United States
Description: High Amenity Value - read on. 5 Minutes from Deep Creek Lake activities. Short distance to Wisp Ski Resort. Walking distance to 'Stopping by Wo... Learn More
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3 bedroom Vacation Rental Home in Mchenry
Home: 3 Bedroom, 2 Bathroom, Sleeps 10
Location: Mchenry, Maryland, United States
Description: quality chalet tucked in the woods. 5 Minutes from Deep Creek Lake activities. Short distance to Wisp Ski Resort. nearby indoor Aquatic Center o... Learn More
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Non Smoking


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Studio Vacation Rental Home in Oakland
Home: Studio, 0 Bathroom, Sleeps 4
Location: Oakland, Maryland, United States
Description: Measures have been taken to make this cabin handicap accessible so our friends who may be limited to a wheelchair can still enjoy this outdoor expe... Learn More
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4 bedroom Vacation Rental Home in Swanton
Home: 4 Bedroom, 3 Bathroom, Sleeps 8
Location: Swanton, Maryland, United States
Description: Short walk to Lake and Deep Creek State Park. Across the street from Deep Creek Lake State Park. TRY OUT NEWLY BUILT 'NATURAL GRILL' - JUST LIKE ... Learn More
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3 bedroom Vacation Rental Cabin in Oakland
Cabin: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: Oakland, Maryland, United States
Description: 5 Minutes to Resort, Dock/Lake short walk. Relax at the picnic table, surrounded by evegreens and Rhododendron and feel like you have your own pa... Learn More
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3 bedroom Vacation Rental Cabin in Mchenry
Cabin: 3 Bedroom, 3 Bathroom, Sleeps 10
Location: Mchenry, Maryland, United States
Description: Private setting, minutes to Lake. Private setting yet minutes to all Lake activities Minutes to WISP ski resort, Restaurants, Night Clubs, Marina... Learn More
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6 bedroom Vacation Rental Home in St. Michaels
Home: 6 Bedroom, 6 Bathroom, Sleeps 12
Location: St. Michaels, Maryland, United States
Description: Estate Privacy Secs from St Mikes - Shoreline, Acreage, Pool, Decor, Hot Tub. Angel Cove Farm is the perfect name for this exquisite country estat... Learn More
Rates
$1192 - $2222 night
$9280 - $12030 week


Non Smoking   Swimming Pool   High-Speed Internet


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2 bedroom Vacation Rental Cottage in Oakland
Cottage: 2 Bedroom, 2 Bathroom, Sleeps 10
Location: Oakland, Maryland, United States
Description: Minutes to Swallow Falls, Deep Creek Lake. Great central location 3 minutes from Swallow Falls State Park with Maryland's highest waterfall 5 mi... Learn More
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4 bedroom Vacation Rental Home in Oakland
Home: 4 Bedroom, 3 Bathroom, Sleeps 9
Location: Oakland, Maryland, United States
Description: Affordable Lake Access/Dock - modest home. Private dock slip with nice setting and spectacular views Feeling of privacy Minutes from Central Deep ... Learn More
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4 bedroom Vacation Rental Home in Easton
Home: 4 Bedroom, 4 Bathroom, Sleeps 10
Location: Easton, Maryland, United States
Description: Elegantly furnished and located in a prestigious estate area of Talbot County, Blue Gates offers a chance to experience the best in Eastern Shore L... Learn More
Rates
$714 - $1028 night
$2971 - $4801 week


Non Smoking   Swimming Pool


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1 bedroom Vacation Rental Cottage in Swanton
Cottage: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Swanton, Maryland, United States
Description: Prime fishing opportunity, on a budget. Short stroll to the Savage River, with nice pools for swimming and fishing Large, level yard offers plenty... Learn More
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