Best price vacation rentals in Oakland, MD 21550, USA • 28 Listings

Oakland, MD 21550, USA Vacation Rentals | 

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United States Maryland Oakland vacation rental compare prices direct by owner 24899197
5.0 · 41 reviews
Map pinOakland, Maryland
Secluded Oakland House w/ On-Site Hiking!
3 Bedrooms4 Beds9 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$222
Booking.com
Booking.com
$256
Vrbo
Vrbo
$209
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United States Maryland Oakland vacation rental compare prices direct by owner 317569
5.0 · 83 reviews
Map pinOakland, Maryland
Glamping - Cozy Hut Delta
1 Bedroom2 Beds4 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$95
Vrbo
Vrbo
Not listed
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United States Maryland Oakland vacation rental compare prices direct by owner 655071
5.0 · 144 reviews
Map pinOakland, Maryland
Molly
1 Bedroom1 Bed2 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$128
Vrbo
Vrbo
Not listed
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United States Maryland Oakland vacation rental compare prices direct by owner 703275
5.0 · 57 reviews
Map pinOakland, Maryland
Valley of Hope Retreat
6 Bedrooms10 Beds16 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$300
Vrbo
Vrbo
Not listed
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United States Maryland Oakland vacation rental compare prices direct by owner 799209
5.0 · 72 reviews
Map pinOakland, Maryland
Glamping - Cozy Hut - Ardennen
1 Bedroom2 Beds4 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$95
Vrbo
Vrbo
Not listed
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United States Maryland Oakland vacation rental compare prices direct by owner 879224
5.0 · 109 reviews
Map pinOakland, Maryland
Private Unit on Farm with Kitchen & Balcony
1 Bedroom1 Bed2 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$160
Vrbo
Vrbo
Not listed
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United States Maryland Oakland vacation rental compare prices direct by owner 1061377
5.0 · 151 reviews
Map pinOakland, Maryland
SUGARBUSH - Sweet Serenity Tiny House
1 Bedroom1 Bed4 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$150
Vrbo
Vrbo
Not listed
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United States Maryland Oakland vacation rental compare prices direct by owner 1075472
5.0 · 166 reviews
Map pinOakland, Maryland
The Original Hob
1 Bedroom1 Bed2 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$125
Vrbo
Vrbo
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United States Maryland Oakland vacation rental compare prices direct by owner 1359084
5.0 · 91 reviews
Map pinOakland, Maryland
Glamping - Cozy Hut - Cortina
1 Bedroom2 Beds4 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$97
Vrbo
Vrbo
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United States Maryland Oakland vacation rental compare prices direct by owner 1393475
5.0 · 96 reviews
Map pinOakland, Maryland
Glamping - Cozy Hut - Uzes
1 Bedroom2 Beds4 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$95
Vrbo
Vrbo
Not listed
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United States Maryland Oakland vacation rental compare prices direct by owner 1430365
5.0 · 82 reviews
Map pinOakland, Maryland
Glamping - Cozy Hut - Stanley
1 Bedroom2 Beds6 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$83
Vrbo
Vrbo
Not listed
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United States Maryland Oakland vacation rental compare prices direct by owner 1917607
5.0 · 57 reviews
Map pinOakland, Maryland
Private Unit on Peaceful Farm, Convenient to Lake
1 Bedroom1 Bed2 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$150
Vrbo
Vrbo
Not listed
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United States Maryland Oakland vacation rental compare prices direct by owner 2051101
5.0 · 39 reviews
Map pinOakland, Maryland
Barn Suite with Kitchen, Jacuzzi & Fireplace
1 Bedroom1 Bed2 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$150
Vrbo
Vrbo
Not listed
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United States Maryland Oakland vacation rental compare prices direct by owner 2124374
5.0 · 61 reviews
Map pinOakland, Maryland
Charming Converted Barn Suite
Private room2 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$140
Vrbo
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United States Maryland Oakland vacation rental compare prices direct by owner 2666997
5.0 · 50 reviews
Map pinOakland, Maryland
Sheila’s Cottage 10 minutes to anywhere
2 Bedrooms5 Beds4 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$171
Vrbo
Vrbo
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United States Maryland Oakland vacation rental compare prices direct by owner 3054765
5.0 · 47 reviews
Map pinOakland, Maryland
Lil' Sumpin
1 Bedroom1 Bed2 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$162
Vrbo
Vrbo
Not listed
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United States Maryland Oakland vacation rental compare prices direct by owner 10583452
5.0 · 40 reviews
Map pinOakland, Maryland
One bedroom Loft-15 from WISP & close to Walmart
1 Bedroom1 Bed2 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$53
Vrbo
Vrbo
Not listed
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United States Maryland Oakland vacation rental compare prices direct by owner 10607993
5.0 · 10 reviews
Map pinOakland, Maryland
Apt -close to Garrett Hosp & OaklandNurse&Rehab
1 Bedroom1 Bed2 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$53
Vrbo
Vrbo
Not listed
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United States Maryland Oakland vacation rental compare prices direct by owner 24244756
5.0 · 30 reviews
Map pinOakland, Maryland
Victorian Farmhouse with view of pleasant valley
5 Bedrooms6 Beds10 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$160
Vrbo
Vrbo
Not listed
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United States Maryland Oakland vacation rental compare prices direct by owner 347075
4.5 · 2 reviews
Map pinOakland, Maryland
Lost Bearadise: Lake Area, Indoor Hot Tub, Fireplaces, Foosball, A/C!
3 Bedrooms1 Bed8 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
Not listed
Vrbo
Vrbo
$144
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United States Maryland Oakland vacation rental compare prices direct by owner 2668030
4.5 · 4 reviews
Map pinOakland, Maryland
Beautiful 65 Acre Farm with Wrap Around Porch
6 Bedrooms1 Bed12 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
Not listed
Vrbo
Vrbo
$795
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United States Maryland Oakland vacation rental compare prices direct by owner 12927921
4.3 · 285 reviews
Map pinOakland, Maryland
Oak Mar Motel
Private room4 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
Not listed
Booking.com
Booking.com
$92
Vrbo
Vrbo
Not listed
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United States Maryland Oakland vacation rental compare prices direct by owner 19185884
4.3 · 284 reviews
Map pinOakland, Maryland
Oak Mar Motel
Private room5 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
Not listed
Booking.com
Booking.com
$94
Vrbo
Vrbo
Not listed
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United States Maryland Oakland vacation rental compare prices direct by owner 528513
4.0 · 8 reviews
Map pinOakland, Maryland
The Herrington: Largest Rental In MD, Indoor Pool, Home Theater
10 Bedrooms1 Bed34 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
Not listed
Vrbo
Vrbo
$1,864
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United States Maryland Oakland vacation rental compare prices direct by owner 2448804
4.0 · 14 reviews
Map pinOakland, Maryland
Vintage Oakland @ Oakland Maryland
4 Bedrooms8 Beds10 Guests
Avg/Night(Excl. Fees)
Airbnb
Airbnb
$299
Vrbo
Vrbo
Not listed
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