Private Vacation Homes in Oakland, the USA

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July 2026
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Tuesday 28 July 2026 - Wednesday 29 July 2026 (1 night)

28 Jul 2026
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29 Jul 2026
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2 Adults - 0 Child
1 room

Oakland - 119 Private Vacation Homes to Choose From

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Oakland - 119 Properties found

Most booked in last 6 months
Recommended
Star rating
Price
Top rated by customers
Deals
Mountain Ridge Nest
Mountain Ridge Nest

143 Jeffrey Lane 20b

Après Chablis
Après Chablis

589 Mountainview Drive

Amenities

Exceptional

1 review

10
Alla Famiglia
Alla Famiglia

310 Winding Trail Lane

2% giveback on bookings

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Evergreen
Evergreen

175 Whitetail Court

Bear Feet
Bear Feet

74 Timberloft Lane #9

Amenities
At Last
At Last

215 Hidden Cove Court

Fireside Fun
Fireside Fun

282 Skippers Point Road

Amenities
Skydance 5 Bedroom House
Skydance 5 Bedroom House

358 Lake Forest Drive

Amenities
Lazy Bear Cove
Lazy Bear Cove

91 Mary's Lane

Amenities
Dancing Bears Retreat
Dancing Bears Retreat

205 Deerfield Drive

Marina One
Marina One

7 Fox Den#1 Lower

Sunset Pointe
Sunset Pointe

2045 Lake Shore Drive

Amenities
Mountain Freedom
Mountain Freedom

705 Mountainview Drive

Wooded Bliss
Wooded Bliss

1389 Mayhew Inn Road

Amenities
American Pride
American Pride

16 Lichen Lane

Amenities

Top Picks for Private Vacation Homes in Oakland

Try one of these popular top-rated private vacation homes in Oakland

Explore Oakland

Discover new destinations in Oakland and find your next stay!
FAQs About Private Vacation Homes in Oakland
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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Hotel Bookings

  • When will I receive my hotel confirmation email?

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    You will receive your accommodation booking confirmation within 24 hours of placing your reservation. We also recommend to check your junk mail or spam folder for your itinerary.

    Please also note that you can always view your booking status online using My Trip on our website or by signing in and selecting My Bookings from the account menu.

    Cryptocurrency payments require a certain number of blockchain confirmations for the booking to proceed. The number of blockchain confirmations required for the most commonly used payment options are as follows:

    • BTC payments: 3 confirmations
    • ETH payments (incl. ERC20): 20 confirmations
    • BNB payments (incl. BEP20): near-instant
    • TRON payments (incl. TRC20): near-instant
  • What is the maximum number of rooms that I can book per booking?

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    You can book up to four rooms per booking. For group bookings that exceed four rooms, please contact our Customer Support Team via [email protected].

  • When will I receive my hotel confirmation email?

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    Hotel reservations are usually confirmed within 60 minutes of booking.

    Once confirmed, your official hotel itinerary will be emailed to you. 

    Where to track booking status

    You can view your booking status via My Trips on our website, or the My Bookings section of your account dashboard.

     

    If you need further assistance, please contact our Customer Support team via Live Chat or email [email protected].

    To help us resolve this quickly, please provide your Order Number and your Transaction Hash / Proof of Payment.

     

  • Why isn't there any hotel availability showing?

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    If our website displays no availability, that unfortunately means we have no available rooms at your chosen property for your preferred dates. Please try updating your search criteria with new dates or filters.

    If your travel arrangements are not flexible and you must stay at this property, please live-chat us or submit a Contact Us form for assistance.

  • My order is expired

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    If your flight, hotel, activity, or car rental booking shows a status of expired after you made a payment, please do not attempt to rebook. Bookings automatically expire if a payment is not fully confirmed within our 10-minute window.

    Why did my booking expire?

    Due to fluctuating product rates and real-time currency or cryptocurrency exchange shifts, we limit the initial reservation window to 10 minutes. The reservation will be marked as expired if a successful payment confirmation is not received before this timer runs out.

    I already sent the payment, what happens next?

    Some payment methods, particularly cryptocurrency transactions, can experience blockchain network delays, exceeding our reservation window. Once the payment is detected, our system will automatically attempt to make the reservation again. 

    What should I do if my booking fails after payment is made?

    Our team will find you another alternative for your booking. If there are no suitable alternative options available, we will refund the amount you paid.

     

    If you haven't receive an email after 60 minutes, please reach out to speak to our Customer Support team via Live Chat or email [email protected].

    To help us resolve this quickly, please provide your Order Number and your Transaction Hash / Proof of Payment.

  • Is there any discount available if I do not have any AVA tokens?

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    Each accommodation and activity booking made on Travala will receive a 2% giveback in the form of AVA tokens. In order to receive this giveback, simply activate your FREE Smart Basic account. The giveback will be credited directly to your wallet after you complete your stay. If you don’t have a Travala account yet, create an account here

  • What should I do if my hotel booking expires or fails after payment is made?

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    Please contact our Customer Support team via chat or email [email protected] and the team will find you another alternative for your booking. If there are no suitable alternative options available, we will refund the amount you paid.

  • How do we determine our hotel sort and filter order?

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    Sort and Filter functions in the search result page support you in finding the best accommodation offers as quickly as possible.

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        • Sort function at the top of the search page enables you to order accommodation search results according to your preference, such as price, rating, distance, guest recommendation, and other criteria.
        • The Filter function enables you to include or exclude various options to suit your travel needs.

    By default, if you do not use either Sort or Filter function, your search results may be ordered based on two factors:

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        • The nearest distance to the destination/landmark you searched for
        • Property ratings based on top reviews

    SORT

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        • Price: sorts your search results based on the property price from high to low and low to high
        • Rating: sorts your search results based on the accommodation star rating from 5 stars to 1 star and 1 star to 5 stars.
        • Distance from downtown: sorts properties nearest to the location you searched for.
        • Property Rank: sorts properties based on transactional data and details about the property.
        • Top Rated: sorts properties with the outstanding ratings based on our data.
        • Guest Recommended: sorts by the percentage of guests who recommend staying at this property. Use this option to get the properties with the highest recommendation score display first.

    FILTER

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      • Search Hotels: filters properties by name once the hotel/property name is entered.
      • Price per night: filters properties by price range once the minimum and maximum price range is selected.
      • Popular Filters: we show the most common filters here that help you easily find the best choice from one or more filters.
      • Star Rating: filters by desired minimum star rating, e.g. only 5-star hotels, both 4-star and 5-star hotels, etc.
      • Guest Review: filters by guest review types, including Excellent, Very Good, etc.
      • Property Type: filters by property types, e.g. Hotel, Villa, Apartment, etc.
      • Amenities: filters by desired amenities, e.g. Swimming Pool, Free WiFi, etc.
      • Hotel Chain: filters by properties that belong to a particular hotel chain.
  • How can I obtain a payment receipt or invoice for my hotel booking?

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    To request a payment receipt or invoice for your hotel booking, please submit a Contact Us request form. Once your request is received we will email you an electronic receipt.

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