Private Vacation Homes in Oakland, the USA

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Wednesday 21 October 2026 - Thursday 22 October 2026 (1 night)

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2 Adults - 0 Child
1 room

Oakland - 139 Private Vacation Homes to Choose From

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Nature's Retreat
Nature's Retreat

800 N BLAKESLEE RD

Amenities
Lakeside Memories
Lakeside Memories

464 LAKE FOREST DR

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Lasting Impressions
Lasting Impressions

106 Timberloft Lane Unit 7

2% giveback on bookings

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Valhalla
Valhalla

74 Grandview Drive

Amenities
Bears Lair
Bears Lair

94 LEHMAN LN

Amenities
Sunset Pointe
Sunset Pointe

2045 LAKE SHORE DR

Amenities
Logxurious
Logxurious

210 PARADISE HTS

Amenities
Bearadise
Bearadise

60 Black Bear Court

Amenities
Fireside Fun
Fireside Fun

282 Skippers Point Road

Amenities
VVS - Very Very Special
VVS - Very Very Special

19906 GARRETT HWY

Amenities
Lakeland Views
Lakeland Views

20241 Garrett Hwy #3

Paradise Getaway
Paradise Getaway

943 Paradise Heights Rd.

Loft of Luxury
Loft of Luxury

135 Jeffrey Lane

Amenities

Excellent

2 reviews

8.0
Santa Fe Getaway
Santa Fe Getaway

33 Santa Fe Trail

Bear Hollow Lodge
Bear Hollow Lodge

20590 GARRETT HWY

Amenities

Top Picks for Private Vacation Homes in Oakland

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The best place to stay in Oakland is Wisp Resort for its high-quality rooms and scenic beauty.
Destination

Discovering Oakland's Coastal Charm and Urban Wonders

Discover what to do and what to see in Oakland

Escape to the tranquil beauty of Oakland, Maryland in the heart of the USA, and discover a hidden gem waiting to be explored. At Travala.com, our private vacation homes in Oakland offer the perfect retreat for nature lovers and adventure seekers alike. Nestled in the breathtaking Allegheny Mountains, Oakland is a destination steeped in charm and surrounded by natural wonders. Explore the stunning Swallow Falls State Park, home to the majestic Muddy Creek Falls, where cascading waterfalls and lush forests create a picturesque backdrop for hiking, biking, and picnicking. Immerse yourself in history with a visit to the Oakland B&O Railroad Museum, where you can step back in time and learn about the region's rich railroad heritage. For architecture enthusiasts, the historic Oakland Train Station is a must-see, showcasing Victorian elegance and timeless charm. Embark on a scenic drive along the stunning Deep Creek Lake, where sparkling waters and rolling hills offer endless opportunities for boating, fishing, and water sports. Take in the panoramic views from the top of Wisp Resort, an all-seasons destination offering skiing, golfing, and zip-lining adventures. At Travala.com, we strive to make your booking experience seamless and convenient. We offer various payment options, including credit cards, debit cards, and cryptocurrencies like Bitcoin, so you can choose the method that suits you best. Indulge in the natural beauty and rich history of Oakland, Maryland, while enjoying the comfort and privacy of our private vacation homes. Book your stay with Travala.com and create memories that will last a lifetime.

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  • How do I select the cryptocurrency payment option during the booking process?

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    Once you’ve selected your desired hotel, flight or activity, you’ll be prompted to enter the necessary personal information (e.g. guest details for hotel check-in or passport information for international flights). After this step, you’ll have 100+ payment options to choose from. 

    Simply select the cryptocurrency you wish to use from:

    • the dropdown list, or
    • choose to pay with crypto via our payment partners, such as Binance Pay

    You’ll then be provided with a QR code and wallet address. Either scan the QR code with your wallet of choice or manually enter the wallet address and the associated cryptocurrency amount displayed in your wallet (note: NOT the fiat value). Then, complete the transaction using your wallet.

    Once the payment is sent and confirmed on the blockchain network, the booking process will be completed. You’ll receive confirmation of your reservation via email, which will include all your tickets and booking details. Refer to our step-by-step guide for more information.

  • Which cryptocurrencies are accepted as payment on Travala?

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  • How many payment options does Travala currently accept?

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  • Are there any loyalty programs or rewards for using cryptocurrencies for bookings on Travala?

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  • What customer support options are available if I encounter issues during my booking process?

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  • What happens if the cryptocurrency price changes between the time of booking and payment confirmation?

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