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Holiday Rentals with Pools in Oakland, MD

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    Travellers to Oakland are booking March dates now. Secure your holiday rental today, and have the perfect trip.
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    1 / 19
    4.5 of 5 stars (12) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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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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    1 / 12
    4.5 of 5 stars (5) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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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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    Amenities & Details
    • Hot Tub
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
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    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
    4 of 5 stars Reviewed 12 January 2011
    We stayed here for a weekend to celebrate my husband's 30th birthday. We had a great time, loved the open floor plan, the girls could play cards while the boys played pool. While...
    5 of 5 stars Reviewed 2 December 2010
    The unit is in wxcellant shapr. The condition has first class utensils.
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    1 / 18
    4.5 of 5 stars (14) Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 17 | Quick View
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    • Hot Tub
    • Air Conditioning
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    Packed with amenities, Splash Mountain offers a spacious vacation home with superior looks inside and out. Situated atop Marsh Mountain on an expansive 3 ½ acres, this Deep Creek rental offers privacy and stuffing views. The home offers 6 bedrooms, as well as a state-of-the-art fitness room, an... View all property information
    Location Information
    Oakland, Garrett County
    4 of 5 stars Reviewed 13 March 2012
    Stayed here for a weekend. House was in a good location up on the mountain. Beautiful new golf course across the street. Great mountain and lake view. Indoor pool and party...
    4 of 5 stars Reviewed 6 January 2011
    We had a good time but it was cold upstairs the first two days but once it got warmer outside it was OK. Cook was hard because the pans weren't in good shape and the knives were...
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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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    • Hot Tub
    • Air Conditioning
    • Sauna
    • Private Outdoor...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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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
    4 of 5 stars Reviewed 10 November 2011
    We stayed at the Ritz on the Lake in Oct...it was very nice!! The house is well kept, clean and supplied with lots of useful pots, pans, utensils, etc. The only problem was that...
    5 of 5 stars Reviewed 20 August 2011
    Ritz on the Lake is a great place for a big family. It had everything we could want and we made use of all the amenities.
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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
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
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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
    3 of 5 stars Reviewed 20 August 2012
    The house have plenty of space, but lacks of beds. We were 6 adults and 4 kids. The website claims that the house has beds for 10 people: 1 King bead, 1 queen bed, 1 bunk bed and...
    3 of 5 stars Reviewed 30 September 2010
    The house and area is lovely. And very user friendly. There were a few disappoointments the oven did not work. and the beds could be more comfortable down stairs.
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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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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
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    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
    5 of 5 stars Reviewed 26 November 2012
    The Drift away was the perfect venue for our family reunion/Thanksgiving. The house has multiple living areas, a nice game room area and plenty of outdoor space so that everybody...
    3 of 5 stars Reviewed 1 January 2012
    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 / 14
    5 of 5 stars (14) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
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    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 16 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...
    5 of 5 stars Reviewed 30 May 2013
    Our group truly enjoyed our extended weekend at Cedar Lodge. It was a very cozy home with room enough for everyone to find couch for reading. Really enjoyed the front porch...
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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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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    If bigger is better, this fantastic chalet is the absolute best! Timberlodge excels in every way imaginable when it comes to your comfort and pleasure. This exquisite log home masterpiece offers 100 feet of beautiful lakefront decorated with fragrant mountain laurel and towering hardwoods. Elegant... View all property information
    Location Information
    Oakland, Garrett County
    4 of 5 stars Reviewed 5 March 2013
    Had a blast at Timberlodge. Highly recommended. Slept 23 of us comfortably. Lake right out back. Great stay!
    4 of 5 stars Reviewed 17 January 2012
    Services were great. Service calls were performed timely and professionally. The home had everything to make our stay one to remember. The layout of the home was great for our...
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    1 / 19
    4 of 5 stars (10) Very good
    8 Bedrooms, 7 Bathrooms, Sleeps 24 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor...
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
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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
    3 of 5 stars Reviewed 3 January 2011
    "Awesome View" needs a remake! The house layout was great and it's location - Great! But the Cleanliness was poor! All Six (6) Bathroom Shower Heads are rusted!! The Top Floor...
    4 of 5 stars Reviewed 10 December 2010
    It was quite a blessing to be able to bring my family back together after so many years of separation after my grandfather passed. This house fully accommodated our needs while...
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    1 / 18
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
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    About this property
    This beautiful lake home instantly welcomes you as you arrive with a natural stone fireplace reaching up to cathedral ceilings and windows looking out to the mountain surroundings and Deep Creek Lake. Exquisite furnishings and unique architectural features throughout create an elegant feel with an... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 21
    4 of 5 stars (9) Very good
    9 Bedrooms, 9 Bathrooms, Sleeps 26 | Quick View
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    Amenities & Details
    • Sauna
    • Hot Tub
    • Air Conditioning
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
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    About this property
    Look beyond the beautiful furnishings and the numerous amenities and you will find peaceful relaxation with incredible panoramic views of Deep Creek Lake and the surrounding mountains. Nestled “Under the Stars” in Mountainside, this recently redecorated chalet is sequestered away from the beaten... View all property information
    Location Information
    Oakland, Garrett County
    5 of 5 stars Reviewed 19 July 2012
    Under the Stars served as a focal point for 25 family members to gather and celebrate a recent graduation. It spaciousness allowed ample room for many different personalities to...
    4 of 5 stars Reviewed 22 September 2010
    Everything was great; however, the tv's in the rooms needs a serious upgrade and we were disappointed that the driving video game did not work.
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    1 / 18
    4.5 of 5 stars (12) Very good
    8 Bedrooms, 9 Bathrooms, Sleeps 24 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Sauna
    • Hot Tub
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
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    About this property
    Elegant, Extravagant, Extraordinary…and the list goes on! Uncommon quality can be found in the smallest details of this grand chalet. Possessing a spectacular, sweeping view of Deep Creek Lake and its lush mountains, Peregrine’s Perch is a premium home that is flawless in design and filled with... View all property information
    Location Information
    Oakland, Garrett County
    4 of 5 stars Reviewed 15 June 2011
    We had a wonderful week stay at Peregrine's Perch. Our group included an 84-year old, eight 18 year olds, parents, cousins and neighbors. The PROS: The house accommodated...
    5 of 5 stars Reviewed 5 January 2011
    Weve stayed at this property multiple times and it still amazes us how much of a great time we have with a house full of amenities. You almost never have to leave with all the...
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    1 / 11
    4 of 5 stars (6) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Hot Tub
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    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
    5 of 5 stars Reviewed 27 October 2011
    We love the Blakeslee neighborhood. Great for riding bikes - easy grade, minimial neighborhood traffic. Great indoor pool and community center - wish there were morning pool...
    3 of 5 stars Reviewed 31 January 2011
    We planned this trip around snowboarding, skiing and tubing. We were none too pleased when we returned from a cold day on the mountains to discover we had no hot water. We...
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    1 / 32
    8 Bedrooms, 8 Bathrooms, Sleeps 26 | Quick View
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    Amenities & Details
    • Private Indoor Pool
    • Air Conditioning
    • Grill
    • DVD Player
    • Sauna
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
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    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
    1 / 12
    4 of 5 stars (3) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
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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
    3 of 5 stars Reviewed 27 August 2010
    The house was spacious inside and well-maintained. The housekeepers had done an excellent job. We enjoyed the secluded property and all the amenities of Blakeslee.
    4 of 5 stars Reviewed 13 August 2010
    We really enjoyed the house. It was very pretty inside and out and very roomy for a 3 BR house. The location was very secluded, so if you're looking for privacy while also being...
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    1 / 37
    4 of 5 stars (2) Very good
    10 Bedrooms, 10 Bathrooms, Sleeps 34 | Quick View
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    • Air Conditioning
    • Hot Tub
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
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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 20 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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