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Oakland Pet Friendly Rentals

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    Travelers to Oakland are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    42 Matching Rentals in OaklandView all 255 rentals
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    Red Run Cabin1 / 22
    (29)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Linwood1 / 18
    (7)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Hemlock Chalet1 / 15
    (5)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    About this property
    At shaded and secluded Hemlock Chalet, you'll find a perfect fusion of nature and homey comforts! Hemlock Chalet is a hit! Located in the prestigious Blakeslee community, this marvelous chalet offers your favorite amenities and all the little luxuries you are looking for in a vacation retreat....
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    Oakland, Garrett County 21550 
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    ON SPECIAL: 15% OFF ARRIVALS WITHIN 2 WEEKS OF BOOKING! (Excludes holidays, discount auto-applied during price quote) Are you looking for a private, quiet getaway?  Look no more, this unique cabin with hot tub & fireplace is minutes from Swallow Falls State Park! Main Floor:  Living Room...
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    Oakland, Garrett County 21550
    Cabin - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    Creature Comforts1 / 20
    (9)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    About this property
    The modern and stylish touches of Creature Comforts make this home the envy of all others! Don't miss the comforting splendor of this fabulous lakefront resort home! Creature Comforts promises to provide a series of little luxuries and patent charms guaranteed to make you feel relaxed and warm....
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    Oakland, Garrett County 21550 
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    About this property
    Simply Cozy Describes this Lovely Duplex Unit at Deep Creek Lake Perfectly!  Once you step through the front door of this lake area unit, you will instantly feel the warmth surround you. A gorgeous corner kitchen greets you with a beautiful contrast between the wood accents and black and stainless...
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    Oakland, Garrett County 21550
    Condo/Apartment - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Enjoy this Quaint and Cozy Deep Creek Lake Log Cabin for Your Vacation Getaway! This cute white washed home located in the Deep Creek Lake log cabin community of Yellowstone Village is waiting for your small family or romantic getaway. The covered front porch beckons you to step inside, take your...
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    Oakland, Garrett County 21550
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    About this property
    What an adorable log cabin home! Whitewater Lodge is a three-bedroom log home in the picturesque Yellowstone Village cabin community in the central Deep Creek area. Inside, the charming wood styling, open layout, and fun vacation amenities transform this charming little cabin into a modern retreat...
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    Oakland, Garrett County 21550
    Cabin - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Morning Breeze1 / 21
    (9)Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    Wide open spaces await you at Morning Breeze! This lakefront home gives you a taste of the good life! Located along the banks of sparkling Deep Creek Lake, Morning Breeze is the perfect spot for your next family vacation! The great room boasts a warm stone fireplace, as well as cathedral ceilings,...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Always in Season1 / 13
    (8)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
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    About this property
    Come sun or snow, this home is “Always in Season!” Celebrate the seasons at this lakefront home! The seasons have never been more beautiful than at Always in Season! Sunbathe and water ski in the warm summer months, celebrate fall with a hike through bright leaves, patter gently through pristine...
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    Oakland, Garrett County 21550 
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    Paradise Lodge1 / 22
    (4)Average
    5 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
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    About this property
    Some of the best lake views can be found at Paradise Lodge! This home is full of timeless appeal! Enjoy fresh mountain air, tall trees, and stunning lakefront views at Paradise Lodge. This classic lodge-style lake home offers seclusion and privacy, yet boasts a location close to many stores,...
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    Oakland, Garrett County 21550 
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 15
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Don't Miss Out on Staying in a Cute Log Cabin with a Year-Round Hot Tub Room and Two Fireplaces! This adorable log cabin is waiting to make your Deep Creek Lake vacation memorable! Walk up the path and around the bushy pine tree to find a cozy, covered front porch peeking out between even more...
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    Oakland, Garrett County 21550
    Cabin - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Willow Point1 / 14
    (11)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed May 27, 2014
    The location was great, just what we wanted for our lab puppy. Nice big yard going right to the water. The hot tub was great because it was a bit chilly. The house itself is a...
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    About this property
    You'll love the setting of Willow Point, a cozy cottage with sprawling lakefront and classic appeal! Willow Point is a wonder! Fill your days with soft winds and crystal waters at this charming lakefront stone cottage. The delightful décor and exquisite lakefront add together to build a wonderland...
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    Oakland, Garrett County 21550 
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    About this property
    Enjoy Deep Creek Lake in this Original Bungalow Nestled between Towering Pines and Lush Rhododendrons with an Amazing Deck Space, Stone Fireplace, WiFi, and a Boat Slip! Home Layout: Main Level: * Living Room with Fireplace * Kitchen with Breakfast Bar * Dining Area * Bedroom - Queen Bed * Bonus...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    Bunbury Cottage1 / 35
    (3)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Rustic and warm, Bunbury Cottage is a charming Lincoln-lodge style home with lots to offer! Want to try and solve a vacation riddle? What's charming and irresistible, immensely private, with 2 streams running on either side, and guaranteed to refresh your spirit? Here's a hint: it's tucked away...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Experience the Magic of Deep Creek Lake in a Comfortable & Cozy Log Cabin in Yellowstone Village! From the minute you arrive at this warm and inviting 2 bedroom, 1 full bath home, you will escape to a simpler time with all the modern conveniences you desire. The main level envelops you with the...
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    Oakland, Garrett County 21550
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Waterfront Chateau1 / 94
    (4)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    Smoking allowed
    About this property
    Waterfront Chateau delights with a tranquil wooded setting, charming lakefront, and sunny interior! The discriminating guest will appreciate this luxurious lakefront home! Waterfront Chateau is the ultimate rendezvous destination for a getaway among family and friends. Located on a dead end street...
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    Oakland, Garrett County 21550 
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 20
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    Awesome View1 / 19
    (11)Average
    8 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Awesome View is the perfect place to swim, stay, and play! The indoor pool always delights! Get it all at Awesome View! Just beyond the tree line of this magnificent estate, get ready for a very special treat: sweeping, panoramic views of Deep Creek envelop you from the home's private dock. This...
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    Oakland, Garrett County 21550 
    Rental Home - 8 Bedrooms, 7 Bathrooms, Sleeps 24
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    6 Bedrooms, 7 Bathrooms, Sleeps 25 Quick View
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    • Air Conditioning
    • Patio
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious Oakland home is the perfect choice for your next large family gathering. It accommodates up to 25 guests and offers a high-end yet comfortable home base with amenities like two hot tubs, a game room, a dock with your very own slip, and much more! Come live the good life, and bring...
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    Oakland, Garrett County 21550
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 25
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    With charming construction, central location, and upscale furnishings, Trailside Tranquility brings a lot of fun and style to your Deep Creek Lake vacation. Blessed with a rich cherry wood interior and craftsman-style design, this four-bedroom home exudes an air of welcoming hospitality, making it...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Just Breathe Inn1 / 18
    (2)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Immerse in nature! Life is unspoiled and unforgettable at the lakefront of Just Breathe Inn! Leisure time is perfected at Just Breathe Inn! Spellbinding and spectacular, this lakefront chalet is rich with charm. You'll feel rested and ready for adventure when you take in a morning sunrise from the...
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    Oakland, Garrett County 21550 
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 7 Quick View
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    About this property
    Reserve this adorable stone cottage with everything you will need to enjoy a quaint visit to Deep Creek Lake! Feel right at home at Water in the Sky! A wooden door opens to the cozy interior that is truly an original cottage to our area. Step back in time and let the stresses of life roll of your...
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    Oakland, Garrett County 21550
    Cabin - 1 Bedroom, 1 Bathroom, Sleeps 7
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    Making Memories1 / 16
    (1)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Reviewed May 10, 2016
    I stayed here back in January with a group of close friends and family and we were so impressed with this house. It is even more beautiful in person than the photos. The layout...
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    About this property
    Refined elegance meets lakefront living at Making Memories! This exquisite home is a sure thing! This beautiful lake home delivers one warm welcome! From the moment you arrive, this home will surround you in an easy elegance for perfection that feels effortless. With a natural stone fireplace,...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    About this property
    If a quintessential Deep Creek Lake home with tons of vintage charm is what you are looking for, then Lake Shore Haven is the perfect vacation home for you!  This beautiful five-bedroom home is surrounded by towering pines and maple trees.  It offers the feeling of being surrounded by beautiful...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    This home was recently featured on HGTV!! Vacation Easy – This Home is a Renter's Dream! This beautiful and spacious lake access 3 bedroom, 3 full bath chalet is waiting for your family! As you enter this lake themed home you will immediately leave your troubles behind as you are greeted with warm...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Nimba Cabin is waiting for you! Enjoy this mountain chalet perched on a hill overlooking the valley below! As you approach this unique home relaxation will be on your mind from the expansive views, quiet community, and open spaces, while fun is just around the corner at the Deep Creek Lake access...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    Serendipity1 / 46
    (3)Average
    8 Bedrooms, 7 Bathrooms, Sleeps 22 Quick View
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    About this property
    Serendipity! This splendid lake house showcases a sunlit interior, level lakefront, and large deck! Bursting with promise, Serendipity is a vacation retreat unlike anything you have ever seen! Come in, take a look around, and let amazement take hold; every corner of this magnificent lake estate is...
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    Oakland, Garrett County 21550 
    Rental Home - 8 Bedrooms, 7 Bathrooms, Sleeps 22
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    6 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    About this property
    Recent Upgrades Include: * Large indoor pool (28') with indoor and outdoor hot tubs * 13 seat, 5 tier movie theater with 144' screen and surround sound * 5 fireplaces * 16 person custom dining room table, breakfast nook and 5 person breakfast bar * 3 living rooms * Massive bar with pool...
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    Oakland, Garrett County 21550
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 20
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    About this property
    Make Your Lake Memories at this Gorgeous Lake Front Home with Boat Slip Located Just Off Popular Glendale Road! Stay in this well-appointed home and find the luxury you have been waiting for. From the minute you cross the threshold from the cute covered porch, you will find a spacious open floor...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    Stargaze from this Impressive Lake Access Chalet with End of Road Privacy and Sweeping Mountain Views! Walk up to this log chalet and open the door to your Deep Creek Lake vacation. The main level is dramatic beginning with the expansive great room highlighted with a large stone fireplace, a huge...
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    Oakland, Garrett County 21550
    Cabin - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    About this property
    Waltzing Moose Lodge is a Spectacular Lake Access Mountain Log Chalet Perched on Top of Mountainside Overlooking Deep Creek Lake! Take in the breathtaking views and feel like you're standing on top of the world! From the minute you enter this luxurious home, you realize all the comforts you are...
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    Oakland, Garrett County 21550
    Cabin - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    About this property
    Bring the whole family together at this chalet-style Oakland home, complete with a game room, two furnished patios, and a private hot tub. The family dogs are also welcome for a small nightly fee! Just up the road, Deep Creek Lake is an exceptional fishing destination, so don't forget your bait...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    8 Bedrooms, 7 Bathrooms, Sleeps 26 Quick View
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    About this property
    This Spectacular Lake Front Chalet is Waiting for Your Deep Creek Lake Getaway! Unwined is under NEW Ownership and Numerous UPDATES are in Progress!   Have a large group or planning a small family reunion? Unwined is the perfect place to accommodate a large group! This home is located off of...
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    Oakland, Garrett County 21550
    Rental Home - 8 Bedrooms, 7 Bathrooms, Sleeps 26
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    Dog-friendly, lakefront log home on a quiet cove - front deck & shared dock1 / 41
    (1)Terrible
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
    About this property
    Head to Deep Creek Lake for a quiet vacation with family and friends, complete with all the conveniences that comes with being close to town. Your group will have ready access to the lake and the slopes, as well as in-town convenience. And to make your getaway complete, you can bring the family dog...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this lovely, lakefront rental your home away from home when you come to Deep Creek Lake and enjoy amenities like a hot tub, a dock with your own assigned slip, and shared tennis. You'll have the best of both worlds with easy access to the slopes and in-town conveniences. The family dog is also...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Parking
    • Cable/satellite TV
    • Housekeeping Included
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Deep Creek Lake home offers beautiful lake and mountain views.  Sit on the large deck and relax with your favorite beverage while taking in the grand views of Deep Creek Lake.  Or join in the fun and use the lake access to go swimming or float on a raft in the water.   This Deep Creek Lake...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Grill
    • DVD Player
    • Washer
    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy your next family vacation near the shore of beautiful Deep Creek Lake at this dog-friendly, well-appointed home in the woods complete with a furnished deck, a gas grill, and plenty of space for up to eight guests. This home is conveniently close to Garrett Highway for easy access to nearby...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Hot Tub
    • Washer
    • Internet Access
    • Grill
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious enough for a family reunion or a truly memorable holiday celebration, this warm and welcoming cabin in the woods comes with a well-appointed deck and a covered patio with a forest view, an outdoor hot tub, wood-burning fireplace, pool table, and a romantic, in-room Jacuzzi. Up to 10 guests...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travelers have booked this property
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Parking
    • Patio
    • Washer
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With a name that means 'nest' in Farsi, this welcoming and dog-friendly lake house will delight you from the outside in. Marvel at the partial lake views as you cook out on the deck's charcoal grill or soak your cares away in the private hot tub. The whole family is sure to love their stay here!...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Hot Tub
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sitting on 29 acres of forest land, this large cabin is perfect for your next Deep Creek Lake vacation. With an updated kitchen, spacious living area, and private dock access, this charming home has everything needed for a memorable stay. Gather around the outdoor fire pit or take a dip in the...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travelers have booked this property
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    Amenities & Details
    • Parking
    • Grill
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the pleasures of country living at this three-bedroom Oakland home, a dog-friendly Maryland escape with a private deck and firepit, its very own air hockey table, and a wondrous location close to Swallow Falls, the Yough River, and Deep Creek Lake. This two-level cabin is located on an...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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