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Oakland Vacation Rentals

23 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 - 23 of 23


5 bedroom Vacation Rental Home in Oakland
Home: 5 Bedroom, 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... Learn More
Rates
$537 - $1047 night
$2279 - $4773 week


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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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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 - $512 night
$1493 - $2073 week


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3 bedroom Vacation Rental Cottage in Oakland
Cottage: 3 Bedroom, 1 Bathroom, Sleeps 8
Location: Oakland, Maryland, United States
Description: Cute cottage in private setting, minutes to Deep Creek. Large backyard for evening relaxing, private wooded setting Firepit provides for great ev... Learn More
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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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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... Learn More
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5 bedroom Vacation Rental Home in Oakland
Home: 5 Bedroom, 4 Bathroom, Sleeps 14
Location: Oakland, Maryland, United States
Description: Large, Lakefont Luxury - every amenity. 4WD, AWD, or tire chains highly recommended/required during winter months COMPLETE REMODEL & UPDATE in Spr... Learn More
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2 bedroom Vacation Rental Cabin in Oakland
Cabin: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Oakland, Maryland, United States
Description: Cozy cabin 1 mile from Lake Newly built cabin sits minutes South of Deep Creek Lake, convenient to Oakland. Enjoy wireless DSL and unlimited long d... 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 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... Learn More
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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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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. 4WD, AWD, or tire chains highly recommended/required during winter months Quality chalet in a forest setting 3 min... Learn More
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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, 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 ... Learn More
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2 bedroom Vacation Rental Cabin in Oakland
Cabin: 2 Bedroom, 2 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... Learn More
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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... Learn More
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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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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. 4WD, AWD, or tire chains highly recommended/required during winter months Wireless internet Outdoors... Learn More
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3 bedroom Vacation Rental Home in Oakland
Home: 3 Bedroom, 4 Bathroom, Sleeps 6
Location: Oakland, Maryland, United States
Description: Rich log cabin in forest setting. 4WD, AWD, or tire chains highly recommended/required during winter months Oversized Deck overlooking beautiful n... 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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8 bedroom Vacation Rental Home in Oakland
Home: 8 Bedroom, 8 Bathroom, Sleeps 26
Location: Oakland, Maryland, United States
Description: Come and stay at Deep Creek's premier deluxe lakefront property where dreams do come true, and the celebration begins at this exquisite 8 bedroom h... Learn More
Rates
$1328 - $1996 night
$5821 - $9369 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Home in Oakland
Home: 2 Bedroom, 1 Bathroom, Sleeps 6
Location: Oakland, Maryland, United States
Description: Internet, Hot Tub, Pastoral Views. Country setting only minutes to Deep Creek Lake State Park. Large deck and covered porch. Everything new ins... 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. 4WD, AWD, or tire chains highly recommended/required during winter months Private dock slip with nice s... Learn More
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Listings 1 - 23 of 23

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