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Holiday Rentals with Pools in Oakland, MD

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    Travellers to Oakland are booking September dates now. Secure your holiday rental today, and have the perfect trip.
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    1 / 18
    5 of 5 stars (1) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    1 / 18
    4.5 of 5 stars (15) Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 17 | Quick View
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    1 / 19
    4.5 of 5 stars (14) Very good
    9 Bedrooms, 8 Bathrooms, Sleeps 28 | Quick View
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    1 / 19
    4.5 of 5 stars (14) Very good
    8 Bedrooms, 8 Bathrooms, Sleeps 26 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
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    About this property
    Unmatched in style and quality, this fantastic chalet sits lakeside on one of Deep Creek Lake's choicest coves. Recently updated and repainted, the interior boasts three spacious master suites, two fireplaces and an airy loft with a pool table. Savor the excellent view of the lake from inside or... View all property information
    Location Information
    Oakland, Garrett County
    1 / 19
    4.5 of 5 stars (12) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    • Air Conditioning
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
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    About this property
    If you and your dog have a longing for wide open spaces, filled with the sights and sounds of nature, remember Forget-Me-Not when selecting your pet friendly vacation destination! Splendid serenity awaits you at this enchanting haven with it’s spacious lawn and surrounding woodlands. With room... View all property information
    Location Information
    Oakland, Garrett County
    1 / 12
    4.5 of 5 stars (5) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Lose yourself in the beauty of nature at R&R Escape. Featuring a wall of windows in the great room, as well as a cozy sun porch, this unique chalet brings the outdoors in with outstanding results. The spacious layout, casual décor and 2 master suites ensures comfort and ease for a gathering of... View all property information
    Location Information
    Oakland, Garrett County
    1 / 37
    4 of 5 stars (2) Very good
    10 Bedrooms, 10 Bathrooms, Sleeps 34 | Quick View
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    • x
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    About this property
    Looking for a royal retreat? With 17,000 sq. ft., The Herrington will make you will feel as if you were living in a castle. From the circular driveway, beauti ful estate, and 11 acre lake, to the grand entryway, ballroom, and elaborate pool room, attention to detail and luxury are spread throughout... View all property information
    Location Information
    Oakland, Garrett County
    3 of 5 stars Reviewed 19 March 2015
    This was my second time staying at this house and I must say that I was disappointed both times. Although it is a very beautiful house, it has many maintenance problems that need...
    5 of 5 stars Reviewed 29 June 2014
    I can't believe there are no reviews on this property. So feel inclined to make one. I've visited Deep Creek several times now, and absolutely love renting through Railey...
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    1 / 7
    4 of 5 stars (5) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Hot Tub
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    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Located in the prestigious community of Blakeslee, this marvelous pet friendly chalet offers numerous amenities for a vacation retreat. Linger for a moment with your dog on the covered porch and enjoy the spacious yard, large trees, and quietude. Step inside to a beautiful chalet with cathedral... View all property information
    Location Information
    Oakland, Garrett County
    1 / 19
    4 of 5 stars (10) Very good
    8 Bedrooms, 7 Bathrooms, Sleeps 24 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
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    About this property
    Multiply your vacation dreams a thousand times over at Awesome View! Aptly named, this magnificent home affords you a tranquil view of Deep Creek's natural surroundings and your dock offers a truly incredible view of the lake. This distinguished mountain chalet goes beyond the normal into the... View all property information
    Location Information
    Oakland, Garrett County
    1 / 14
    5 of 5 stars (14) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Shared Outdoor Pool...
    • Air Conditioning
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Nestled among the tall oaks and maples, this remodeled pet friendly chalet offers privacy and seclusion within a short walk to the lake. The spacious deck and backyard fire pit set the stage -roast marshmallows, share your favorite stories, rekindle friendship and laugh till your sides hurt.... View all property information
    Location Information
    Oakland, Garrett County
    5 of 5 stars Reviewed 15 August 2014
    Our family, 2 adults and 3 children (12, 15 and 17) plus Snow Lab, Luie enjoyed this spacious 4 bedroom home. Great hot tub. Saw many deer in the wooded backyard. Short walk to...
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    1 / 21
    4 of 5 stars (9) Very good
    7 Bedrooms, 6 Bathrooms, Sleeps 20 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Enter a world as nature intended-unspoiled, unhurried, unforgettable. Luxury takes on new meaning at “Drift Away,” when surveying the immense rooms, well-equipped kitchen, superior furnishings and attention to every detail. Nearly every room offers stunning views. Your dog will love to explore the... View all property information
    Location Information
    Oakland, Garrett County
    3 of 5 stars Reviewed 31 December 2011
    I would give this a rating of slightly below average. I was looking for a house to fit a group of 6 adults for New Years Eve weekend. The bedroom layout fit what I was looking for...
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    1 / 11
    3.5 of 5 stars (7) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
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    About this property
    Located on a large wooded lot, Linwood offers a quiet retreat. Enjoy your early morning coffee on the spacious deck or on those crisp evenings, or just relax in front of a glowing fire. Regardless of season, Linwood provides a comfortable and casual atmosphere with tongue and groove walls, stone... View all property information
    Location Information
    Oakland, Garrett County
    1 / 11
    4 of 5 stars (6) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • ?
    • Smoking allowed
    • x
    About this property
    A festival of family fun awaits you at the dog friendly Blakeslee Retreat! This attractive cedar-sided chalet with its spectacular front wall of windows offers a warm country welcome to the entire family. Beautifully decorated and comfortably furnished, you will relax in style at Blakeslee Retreat.... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 12
    4 of 5 stars (3) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Shared Outdoor Pool...
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    • Pet-friendly
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    • x
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    About this property
    Paradise peppered with ambiance --- Baldwins Domain is the perfect choice for the discerning guest. Linger for a moment on the spacious decks of this elegant home located in the prestigious community of Blakeslee. The superbly decorated rooms are accented with cozy comforters and beautiful... View all property information
    Location Information
    Oakland, Garrett County
    1 / 27
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
    • Internet Access
    • Shared Outdoor Pool...
    • Satellite TV
    • DVD Player
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Classic Americana is a marvelous 4 bedroom/ 2.5 bath lake access home that will surprise and delight you from the moment that you pull into the driveway. Enter from the covered front porch into the majestic Great Room. Embrace the country charm of the hardwood floors, the white washed wooden beamed... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 28
    4.5 of 5 stars (37) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Shared Outdoor Pool...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    American Pride is an inviting 5 bedroom 3 bath chalet nestled among the trees in one of the most requested communities in Deep Creek Lake. A few steps into the home and you will find yourself entering into the elegantly decorated Great Room which features large cathedral ceilings, a massive stone... View all property information
    Location Information
    Oakland, Garrett County 21550
    5 of 5 stars Reviewed 18 February 2015
    We stayed at this location with 10 adults (5 couples) and it was perfect. For a group who loves to cook the kitchen was stocked with everything that was needed. The home felt like...
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    1 / 10
    4.5 of 5 stars (8) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Regardless of weather or time of year, good times are to be had at Blue Waters! This warm and inviting home offers such versatility as a relaxing quiet setting for a couple or a gathering place for family and friends. Blue Waters features a large great room with vaulted ceiling, native stone... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 21
    4.5 of 5 stars (11) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool...
    • Grill
    • Internet Access
    • Hot Tub
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Come and relax at San~Stress, located in the wonderful community of Blakeslee. This property is adorned with hardwood floors, tongue and groove ceilings, and plenty of space for the whole family. The lower level family room is maxed out with a pool table, air hockey game, mini bar, and stereo... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 21
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Shared Outdoor Pool...
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    There is no better place to reunite with friends and family than Nature’s Retreat. This spectacular 5 bedroom lakefront home offers all of the amenities of home and more! Glistening hardwood floors, a massive stone stacked fireplace and leather furnishings create a warm and comforting gathering... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 33
    8 Bedrooms, 8 Bathrooms, Sleeps 26 | Quick View
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    Amenities & Details
    • Waterfront
    • Hot Tub
    • Satellite TV
    • DVD Player
    • Private Indoor Pool
    • Sauna
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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 home known as Celebration at Deep Creek. From the moment that you step inside this luxurious mountain home you will be in awe. Walking through the foyer,... View all property information
    Location Information
    Oakland, Garrett County 21550
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    1 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Grill
    • Parking
    • Internet Access
    • DVD Player
    • Shared Outdoor Pool...
    • Waterfront
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise is a spectacular 4 bedroom lakefront home that will quickly become host to your family’s favorite Deep Creek memories. From the moment that you begin pulling up to the home, you will embrace the charm of the serene tree lined drive. Offering over 4 acres of private lawn, outdoor enthusiasts... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Shared Outdoor Pool...
    • Air Conditioning
    • Grill
    • Satellite TV
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Red Run 1A3 is an alluring 3 bedroom condominium located in the desirable Red Run Community. Summer days don't get better than this as you and your guests relish time spent swimming & playing from the nearby beach area or lounging lazily around the outdoor community swimming pool. Winter evenings... View all property information
    Location Information
    Oakland, Garrett County 21550