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Oakland Vacation Rentals

24 Oakland 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 Oakland, Maryland, United States.
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Listings 1 - 24 of 24


5 bedroom Vacation Rental Home in Oakland - Lake View
Home: 5 Bedroom, 4.5 Bathroom, Sleeps 12
Location: Oakland, Maryland, United States
Description: Your Deep Creek adventure awaits! Reverie is an exquisite 5 bedroom home that will far exceed your expectations. Floor to ceiling windows in the Gr...
Rates
$537 - $627 night
$2278 - $4991 week


Non Smoking


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Featured


4 bedroom Vacation Rental Home in Oakland
Home: 4 Bedroom, 3.5 Bathroom, Sleeps 12
Location: Oakland, Maryland, United States
Description: Memory Lane is a home designed to bring friends and family together for fun and laughter. Tucked among gracious, blossomed trees with a meticulousl...
Rates
$345 - $520 night
$1479 - $2093 week


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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...
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5 bedroom Vacation Rental Home in Oakland - Lake View
Home: 5 Bedroom, 3 Bathroom, Sleeps 12
Location: Oakland, Maryland, United States
Description: Views, Views, Views! Amazing Mountain & Lake views. July 28 - August 29, now accepting 2-night reservations! Imagine being on top of the world, ...
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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...
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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...
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2 bedroom Vacation Rental Home in Oakland - Lake Front
Home: 2 Bedroom, 2 Bathroom, Sleeps 8
Location: Oakland, Maryland, United States
Description: Relax on the enormous deck while taking in views of the lake. meander over the large yard to the water's edge and drop a line in to catch that lar...
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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...
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2 bedroom Vacation Rental Cabin in Oakland
Cabin: 2 Bedroom, 1.5 Bathroom, Sleeps 8
Location: Oakland, Maryland, United States
Description: PLANNING A SKI/TUBING TRIP? Cabin in the Woods provides a secluded private setting and is only 14 miles from the WISP. Check out of monthly specia...
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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...
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5 bedroom Vacation Rental Home in Oakland
Home: 5 Bedroom, 3.5 Bathroom, Sleeps 14
Location: Oakland, Maryland, United States
Description: Large, Lakefont Luxury - every amenity. August 15 - August 29, Saturday check-ins only, 7 night stays only Relax in the Great Room or Rec Room ta...
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5 bedroom Vacation Rental Home in Oakland
Home: 5 Bedroom, 3.5 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...
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4 bedroom Vacation Rental Home in Oakland
Home: 4 Bedroom, 2.5 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 ...
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2 bedroom Vacation Rental Home in Oakland
Home: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Oakland, Maryland, United States
Description: Walk into Herrington Manor State Park. Enjoy a "black hole" vacation with no internet service or blaring tv Small chalet is literally a stone's th...
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4 bedroom Vacation Rental Home in Oakland
Home: 4 Bedroom, 2 Bathroom, Sleeps 8
Location: Oakland, Maryland, United States
Description: Great sledding out your back door, 15 minutes to Resort. Outstanding 360* pastoral views Oversized yard well off County road for safe recreation ...
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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...
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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...
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5 bedroom Vacation Rental Home in Oakland
Home: 5 Bedroom, 4.5 Bathroom, Sleeps 13
Location: Oakland, Maryland, United States
Description: Brand new home, furnished Summer 2014. 2 Master Suites, main level Bedroom, 2 lower level bedrooms Flat screen TV's in every room Game tables do...
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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...
Rates
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Pet Friendly   Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Home in Oakland
Home: 3 Bedroom, 3.5 Bathroom, Sleeps 6
Location: Oakland, Maryland, United States
Description: Rich log cabin in forest setting. Oversized Deck overlooking beautiful native stone landscaped area surrounded by trees. Nestled in the scenic wo...
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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...
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3 bedroom Vacation Rental Home in Oakland
Home: 3 Bedroom, 2 Bathroom, Sleeps 10
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 Stat...
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8 bedroom Vacation Rental Home in Oakland - Lake View
Home: 8 Bedroom, 7.5 Bathroom, Sleeps 26
Location: Oakland, Maryland, United States
Description: Beautiful Lakefront Home w/ Private Indoor Pool, Hot Tub & Dock Slip! Come and stay at Deep Creek's premier deluxe lakefront property where dreams...
Rates
$1397 - $1784 night
$5897 - $9394 week


Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Home in Oakland
Home: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: Oakland, Maryland, United States
Description: Better than a 'park-like' setting!. Great central location for natural resorts 3 minutes from Swallow Falls State Park with Maryland's highest w...
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Listings 1 - 24 of 24

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