Best price vacation rentals in Oakland, MD 21550, USA • 30 Listings
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Oakland, MD 21550, USA Vacation Rentals | 

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5.0 (15)
NEW! Secluded Oakland House w/ On-Site Hiking!
Up to 9 guests
Vrbo$170
Airbnb$187
Average Nightly Rate
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3.2 (6)
DOGS WELCOME! Lake Area Home w/Hot Tub, Fire Pit, & Wood Fireplace!
Up to 12 guests
Vrbo$162
Airbnb$231
Average Nightly Rate
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5.0 (25)
Hobbitat Home Place
Up to 4 guests
Airbnb$296
Average Nightly Rate
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5.0 (70)
Glamping - Cozy Hut Delta
Up to 4 guests
Airbnb$95
Average Nightly Rate
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5.0 (1)
Cozy Cabin w/Indoor Hot Tub, 2 Wood Fireplaces, Foosball Table, & Central A/C!
Up to 8 guests
Vrbo$162
Average Nightly Rate
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5.0 (110)
Molly
Up to 2 guests
Airbnb$148
Average Nightly Rate
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5.0 (36)
Valley of Hope Retreat
Up to 16 guests
Airbnb$250
Average Nightly Rate

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5.0 (57)
Glamping - Cozy Hut - Ardennen
Up to 4 guests
Airbnb$95
Average Nightly Rate
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5.0 (78)
Private Unit on Farm with Kitchen & Balcony
Up to 2 guests
Airbnb$155
Average Nightly Rate

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5.0 (100)
SUGARBUSH - Sweet Serenity Tiny House
Up to 4 guests
Airbnb$150
Average Nightly Rate
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5.0 (132)
The Original Hob
Up to 2 guests
Airbnb$145
Average Nightly Rate
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5.0 (76)
Glamping - Cozy Hut - Cortina
Up to 4 guests
Airbnb$95
Average Nightly Rate
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5.0 (79)
Glamping - Cozy Hut - Uzes
Up to 4 guests
Airbnb$95
Average Nightly Rate
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5.0 (72)
Glamping - Cozy Hut - Stanley
Up to 4 guests
Airbnb$95
Average Nightly Rate
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5.0 (39)
Private Unit on Peaceful Farm, Convenient to Lake
Up to 2 guests
Airbnb$145
Average Nightly Rate
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5.0 (37)
Barn Suite with Kitchen, Jacuzzi & Fireplace
Up to 2 guests
Airbnb$140
Average Nightly Rate
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5.0 (40)
Charming Converted Barn Suite
Up to 2 guests
Airbnb$135
Average Nightly Rate
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5.0 (60)
Oasis in Oakland
Up to 5 guests
Airbnb$112
Average Nightly Rate
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5.0 (25)
Sheila’s Cottage 10 minutes to anywhere
Up to 4 guests
Airbnb$171
Average Nightly Rate
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5.0 (20)
Lil' Sumpin
Up to 2 guests
Airbnb$189
Average Nightly Rate
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5.0 (9)
Vintage Studio Apartment
Up to 2 guests
Airbnb$89
Average Nightly Rate
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4.7 (57)
DOGS WELCOME! Lake Area Home w/Hot Tub, Pool Table, & Jetted Tub!
Up to 14 guests
Vrbo$213
Average Nightly Rate
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4.5 (5)
2BR Loft home Oakland Maryland
Up to 6 guests
Airbnb$175
Average Nightly Rate
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4.5 (4)
Beautiful 65 Acre Farm with Wrap Around Porch
Up to 12 guests
Vrbo$795
Average Nightly Rate
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4.2 (6)
The Herrington-largest rental Estate in MD w / private pool, home theater
Up to 34 guests
Vrbo$1,482
Average Nightly Rate
  1. United States
  2. Maryland
  3. Oakland Vacation Rental Price Comparison

Compare Airbnb vs. Booking.com vs. Vrbo prices for vacation rentals in Oakland, MD 21550, USA

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