Vacation Home Rentals By Owner In Oakland, MD

$699.25

Huge + Quiet + Hot Tub + Theatre Room

Oakland, Maryland, United States

BBoulder Escape just listed with Red Barn Vacations. The home was five star-rated for the past three years of rentals. I'm sure we'll have a flood of five-star reviews on the website soon, but until then, we have no problem reassuring you: you're gonna love this home!brbrBoulder Escape is a picture-perfect mountain escape. Located in central Deep Creek lake, this 6800 sq. ft home is a wonderful escape, year round. With the large interior, brand new hot tub, large media room with 75 HDTV and surround sound,, air hockey, pool table, game room and more, you'll have plenty to keep you entertained and happy. Throughout the lower level, you'll love having a full-size pool table, poker table, air hockey table and mini shuffleboard table. This game room will keep you entertained for days! In the Winter, you are less than ten minutes away from the Wisp Ski Resort for skiing, snowboarding, and snow tubing. Come summer, your lake access is at the community marina just down the mountain. There is also several free community tennis courts a short walk away! One of the best features of this home is simply the privacy and serenity that surround it. When you are hanging out in the hot tub or enjoying the view from the back deck, you'll stare out at nature and trees, not at neighbors or car traffic. For escaping with friends, reuniting with family, or enjoying the pleasures of Deep Creek Lake, the home offers the perfect vantage to do just that.brbrBedroom 1: Main Level Master with King Bed brBonus: Futon in Game Room with Air Hockey Table brBedroom 2: Upper Level Master Bedroom with King BedbrBedroom 3: Upper level bedroom with Two Queens BedsbrBedroom 4: Queen BedbrBedroom 5: Upper Level Bedroom with King Bed brbrLocation Highlights: Located up on the mountainside near the very middle of Deep Creek Lake, this home has all the benefits of a private wooded location with the benefits of being near all your favorite lake activities. The hot tub is tucked away against the woods, out of sight from neighbors, graced with lovely wooded views. Within the community, there are walking trails, a community pavilion, and free tennis courts within walking distance of the home. When leaving the community, popular attractions like the Lakeside Creamery, Ace's Run restaurant. Trader's Coffee Shop, High Mountain Sports and the popular Honi Honi bar are within a short one minute drive. brbr* Winter Advisory: Deep Creek is a mountainous region that experiences more snowfall and ice than you may be used to. Many roads and driveways can be steep. 4WD/AWD vehicles are advised in the winter months. *brbrPlease note: The home has a video-only security camera on the outside of the property. brbrDog-Friendly Notice: Maximum of two dogs per reservation. A $175/non-refundable fee will be added for each dog. Dogs should be well-behaved, trained, and friendly; dogs with a history of aggression or destruction are not permitted. In order to comply with many of our home's rental insurance policies, breeds listed as most aggressive are banned for all rentals, regardless of individual training and temperament. If you are planning to bring a dog, please reach out to us upon booking to discuss your dogs breed to get final approval from our staff.

Bed

Bath

Sleeps

$475.32

/ Nightly

Private Vacation Home

Serene Cabin Getaway w/ Pool Table & Fireplace

Oakland, Maryland, United States

Name: Tree Top Lodge | Bedrooms: 4 | Bathrooms: 3 | Sleeps: 8 | Access: Lake Area | Pets Not Permitted | MUST BE 24+ YEARS TO RENT | Free WIFI ProvidedbrbrDESCRIPTION:brIf you’re looking for a rustic retreat with all the comforts of home, look no further! Tucked away in the Gallatin Woods community, Tree Top Lodge surrounds you with Deep Creek’s natural beauty while offering the convenience of modern amenities. Enjoy your morning coffee on the porch as the breeze passes through the trees, carrying the aroma of your favorite foods cooking on the grill. Then, gather together for a family-style meal around the table, either outside amongst nature or inside by the roaring fireplace. Challenge each other to a pool tournament, settle in for a movie marathon, or take a short drive to enjoy all of Deep Creek’s best restaurants and attractions. Spend nights to remember around the fire pit, storytelling and enjoying each other’s company, and complete the perfect day with a relaxing soak in the hot tub. Your new favorite spot is waiting for you - book your stay at Tree Top Lodge today!brbrACCESS DETAILS:brNo additional details provided for this home.brbrCOMMUNITY/AREA DETAILS:brLocated in the Gallatin Woods Community at Deep Creek Lake.brbrThis home comes with free access to the Community Aquatic Recreation Center (CARC)! This fitness and wellness complex, located in the central Deep Creek Lake area, offers a modern gym and a full-size indoor pool. The free CARC membership is available to all guests in the home for the duration of your stay, up to the home’s full occupancybrbrLAYOUT DETAILS:brMain Level:br- Kitchenbr- Dining Areabr- Living Roombr- Mud Roombr- Full Bath with Shower/Tubbr- Bedroom: Queen Bed, Access to Shared BathbrbrUpper Level:br- Bedroom: Queen Bed, Balconybr- Full Bath with Shower/Tubbr- Bedroom: King Bed, Balcony, Access to Shared BathbrbrLower Level:br- Den/Game Areabr- Full Bath with Shower/Tubbr- Bedroom: Queen Bed, Access to Shared Bathbr- LaundrybrbrDISCLAIMERS:br4WD/AWD or snow tires are always recommended for the area during the Winter months of November – March. For more house specific driveway information, please refer to your app/guest portal after booking.brbrAFTER BOOKING: An email will be sent to the address provided during check-out; please check for action items needed to secure your reservation. The subject of this email will start with URGENT: Complete Your Booking For... and may be in your Promotional/Marketing folders depending on your email provider and settings.brbrTOILETRIES & PAPER PRODUCTS: Bed linens and bath towels provided w/rental. No soaps, toiletries, paper products, trash bags, etc. will be provided with the exception of a welcome bag including a few starter items. Please pack accordingly.brbrNOTE: A copy of the contract holder's Photo ID, a signed contract, and a list of your full travel party (names/ages of all attending) will be required to complete your booking. If booking last minute, you may be required to stop by our main office to show your photo ID and the credit card used on the reservation. This policy is in place to help combat fraudulent activity that is more likely to occur in last-minute arrivals.

Bed

Bath

Sleeps

$827.39

/ Nightly

Private Vacation Home

Huge, Beautiful + Quiet Home with Amazing Amenities

Oakland, Maryland, United States

Hemlock Hideaway offers a vacation experience worth raving about! Starting with the home's standout feature: the back deck! This awesome space combines the beauty, privacy, and tranquility of the surrounding woodlands with some truly amazing amenities, like an outdoor wood-burning fireplace, smart TV, comfortable seating, brand new hot tub, a flattop grill, a traditional propane grill, and a wood-burning outdoor pizza oven! Elsewhere outside, you'll find a fire pit, a swing for the kids, and a corn hole set. If you are someone who likes to play and relax outdoors, this home is for you! Between the outdoor fireplace and the inside, the home boasts a staggering four fireplaces: one wood-burning fireplace on the deck, one wood-burning fireplace in the sunroom, one gas fireplace in the living room, and one gas fireplace in the lower level game room. Talk about cozy! Here's some more crazy numbers for you: the game room is equipped with an arcade game machine loaded a whopping 2200 different games! More of a traditionalist The game room also has a pool table, comfortable sectional, smart TV and wet bar available to entertain you. Between the fun amenities, the beautiful mountain cabin aesthetics, upscale construction, and considered design, this home was built for vacation excellence.brbr* Winter Advisory: Deep Creek is a mountainous region that experiences more snowfall and ice than you may be used to. Many roads and driveways can be steep. 4WD/AWD vehicles are advised in the winter months. *

Bed

Bath

Sleeps

$481.39

/ Nightly

Private Vacation Home

Windsor House | Pet Friendly, Hot Tub, Lake Access

Oakland, Maryland, United States

Windsor House is the perfect choice for vacationers interested in Deep Creek Lake's numerous attractions. Three suites make this elegant chalet ideal for a family retreat or a couples' getaway.brbrThis home of distinction features tasteful decor that lends warmth and cheer to the spacious interior. Dramatic cathedral ceilings, hardwood floors and a stone fireplace define the great room. You can sink into the comfortable furnishings and choose from over 100 DVDs that offer something for all ages!brbrThe chef in your group will love the well-equipped kitchen that is outfitted with stainless steel appliances and lots of counter space. Between the table and breakfast bar, there is ample room for everyone to share homestyle meals. Sliding doors lead to the deck, so you can take dinner outdoors when you are in the mood to barbecue. The screened porch is adjacent to the dining room and offers the perfect spot to sip your morning coffee before a fun-filled day on the water.brbrFurnished with a duobunk, a TV and a DVD player, the main level bedroom is the ideal spot for the kids. They will love this bright and cheerful space! There is also a primary suite with a king bed, TV and DVD player on this floor. Decorated with a good night's sleep in mind, you will awaken refreshed and ready to tackle any adventure.brbrUpstairs, you will find a primary suite that is a private haven where you can completely unwind. It has a king bed, TV, DVD player, wet bar and a full bath with a garden tub and shower. A cozy gas fireplace and a private balcony are added bonuses!brbrFor a fun evening at home, head downstairs to the family room that has a TV, DVD player and a pool table to keep you entertained. Plus, you can keep snacks and drinks handy at the wet bar. There is also a den with a TV, DVD player and double futon to expand your living space.brbrThe third primary suite is located on the lower level. Furnished with a queen bed and a TV, it has everything you need to relax at the end of the day.brbrThere is no need to leave Fido at home when you come to Deep Creek! Windsor House is dog friendly (ask about the additional fee), and the owners even supply a dog crate for his comfort.brbrEveryone will love the truly exceptional outdoor space! The wrap-around deck is the perfect place to soak up some sunshine or to check out the fall foliage. At dusk, gather around the fire pit for s'mores and spooky stories under the stars. When the kids go to bed, you can take a soothing soak in the brand NEW outdoor hot tub.brbrYour community lake access is within a half mile, so you can look forward to swimming and fishing on sunny summer days.brThanks to its convenient location, you are within a short drive from state parks, restaurants, shops, marinas and many other popular activities. A ten-minute drive will take you to Wisp Resort where year round fun awaits! You can ski, golf, snow tube, mountain bike, zipline, ride the mountain coaster and much more. On top of the mountain, you can take a thrilling white water rafting trip with an experienced guide.brbrMake your Deep Creek Lake vacation one to remember - reserve Windsor House today!brbr*Please Note: A 4WD vehicle is required in winter months (November - March).brbrFor your convenience, this home offers free wifi.brbrIf your rental is listed as having a Boat Dock as an amenity provided with this property, this is subject to weather conditions, water levels, and other natural factors.

Bed

Bath

Sleeps

$496.66

/ Nightly

Private Vacation Home

Donnas Choice | Lakefront + Wrap-around Deck

Oakland, Maryland, United States

Have the time of your life when stay at Donna's Choice for your next Deep Creek vacation!brbr Unwind in style at this bright and cheerful contemporary mountain home. Attention to detail is found throughout, and you will notice photos of local landmarks decorating the walls. The main level's open concept living area features leather sofas and sliding doors that frame the view. Watch a movie on the flat screen TV or simply bask in the the warm glow of a crackling fire.brbr The fully-equipped kitchen makes cooking for your group a breeze. Instead of dealing with the hassle of dining out at a restaurant, dining out at Donna's Choice means you get to enjoy the view and the fresh mountain air! There's easy access from the kitchen to the wrap-around deck. It is the perfect spot for family and friends looking to spend the day grilling, playing, and relaxing! When you want to eat indoors, there is plenty of seating at the dining room table.brbr On the main level you will also find a comfortable bedroom with a daybed with a twin trundle. This is a great spot for the kids!brbr Offering a private retreat, the upper level primary suite has a king bed, TV, hardwood floors and vaulted ceilings. After a busy day on the lake or on the slopes, you can take a soothing soak in the oversized jetted tub before retiring for the evening. As an added bonus, you have a private balcony where you can start your day surrounded by the sounds of nature.brbr The remaining sleeping quarters are located on the lower level. Each is furnished with your comfort in mind. Scenic views are yours to behold when you choose the lake front bedroom with a queen, TV and DVD player. Doors open to the deck where you can sit in the sun each morning or do a little stargazing before bedtime.brbr Outside, you will discover that you have found a place where each changing season works its own special magic on the landscape. Enjoy sunny days and green peaks in spring and summer, vibrant foliage lighting up the horizon in the fall and winter views that reveal more of the lake. The yard has room for the kids to run and play while remaining within sight of the deck.brbr A path winds through the trees to your private lake front with a dock for you boat. If you don't have your own, local marinas have got you covered. You can explore the lake's miles of shoreline on sunny summer days, and return to your home-base for swimming and fishing.brbr Just off of the beaten path, you will appreciate the quiet location that is still convenient to area activities. Within a ten to fifteen minute drive, you can reach white water rafting at the Adventure Sports Center, skiing, snow tubing and more at Wisp Resort, miniature golf, arcades, kayak tours and much more. Plus, restaurants and shops are also close-by. Be sure to include a trip to at least one of our state parks in your plans. You can hike to powerful waterfalls at Swallow Falls State Park, rent a canoe at Herrington Manor State Park or tour the aviary at the Discovery Center at Deep Creek Lake State Park.brbr Look no further you have found the ultimate Deep Creek Lake vacation rental in Donna's Choice!brbr For your convenience, this home offers free wifi.brbrIf your rental is listed as having a Boat Dock as an amenity provided with this property, this is subject to weather conditions, water levels, and other natural factors.

Bed

Bath

Sleeps

$372.97

/ Nightly

Private Vacation Home

Retro Lake Landing | Pet Friendly, Great Outdoors!

Oakland, Maryland, United States

Vivid and lively are two words that can describe the character displayed in Retro Lake Landing. Its originality is definitely one of a kind and will certainly put that extra little kick into your vacation. If you are looking for something different, fun and exciting, this would be the perfect choice for you! brbrThis home has a beautiful lakefront with a private boat dock for you to swim, fish, or to watch boats passing by. You also have the convenience of the outdoor hot tub to relax in while enjoying the fresh, crisp mountain air. Towering trees surround the home, so you have the privacy everyone is looking for while retreating from everyday life. brbrEvery feature offered here at Retro Lake Landing is what makes a vacation, a vacation. Experience the charming original Deep Creek in this older cottage that is lakefront and within seconds from the ski slopes. It has it all- the best of both worlds! brbrFor your convenience, this home offers free wifi.brbrIf your rental is listed as having a Boat Dock as an amenity provided with this property, this is subject to weather conditions, water levels, and other natural factors.

Bed

Bath

Sleeps

$370.72

/ Nightly

Private Vacation Home

Some Kind of Wonderful | Spacious Interior + Hot Tub!

Oakland, Maryland, United States

Brimming with charm and convenience, Some Kind of Wonderful is a Craftsman-style home that is ready and waiting to host your next Deep Creek vacation!brbr Get together with your favorite people in the spacious main level where you will feel instantly at home during your time in the mountains. The open layout creates an inviting feel that is enhanced by hardwood floors, tasteful furnishings and lots of natural light. Get cozy by the glow of the fireplace in the great room or watch your favorite show on the flat-screen TV. This will be a popular gathering at the beginning and end of each day filled with Deep Creek adventures.brbr The well-equipped kitchen has everything you need to make delicious meals at home when you are not trying out local restaurants. With plenty of seating at the breakfast bar and dining table, this is a great opportunity to share tasty food and lively conversation as you reconnect with family and friends.brbr Unwind in the main level primary suite with a four-poster king bed and TV that will keep you completely comfortable. The main level bedroom with a queen bed and a TV promises a restful night's sleep. brbr Upstairs, the roomy loft expands your living space. You can hang out and watch your favorite team on TV or deal a hand of rummy at the card table. There is lots of seating, so everyone can find a place to kick-back.brbr When you are ready to retire for the night, the two upper level bedrooms are well-furnished for a good night's sleep. One offers a king bed and the other a duobunk and twin, and both are outfitted with a TV.brbr Lazy days summer days are best spent lounging in the sun on the deck with a cold drink in your hand. You can host an afternoon barbecue or take a soothing soak in the outdoor hot tub under starry mountain skies.brbr Popular with locals and guests alike, you can walk to Dutch's at Silver Tree for an exceptional meal or enjoy lake views at the Harbor Bar. Within less than one mile, you will find Uno's Chicago Grill, Arrowhead Market, Garrett 8 Cinemas and the Honi-Honi Bar.brbr A short drive will lead you to lots of favorite area attractions. Deep Creek Lake State Park offers a sandy beach for swimming, miles of hiking trails, the Discover Center (great for kids!) and much more. Drive in the opposite direction to check out four seasons of fun at Wisp Resort. Experience everything from skiing and golf to snow tubing and ziplines. A ride on their mountain coaster is an absolute must!brbr Reserve Some Kind of Wonderful for your next Deep Creek Lake vacation to ensure an amazing experience is in your future!brbrThings to BringbrbrWe do supply a starter pack that includes a tab for the dishwasher, a small container of dish soap, a small packet of laundry detergent, a sponge, a roll paper towels, a trash bag in all trash cans and a roll of toilet paper in each bathroom. It is recommended that you bring the additional items listed below to supplement the starter kit.brbrPaper TowelsbrToilet PaperbrGarbage BagsbrAluminum FoilbrPlastic WrapsbrDish DetergentbrAll Purpose CleanerbrHand Soap/Bath Soap/Toiletry ItemsbrStaple Items (salt, pepper, sugar, etc.)brCondimentsbrBeach Towels for lake, hot tub, and/or poolbrFirst Aid Kit

Bed

Bath

Sleeps

$1722.31

/ Nightly

Private Vacation Home

Celebration at Deep Creek | Indoor Pool, Game Room, Hot Tub

Oakland, Maryland, United States

Come and stay at Deep Creek's premier lakefront property where dreams do come true, and the fun begins at this exquisite eight-bedroom home with plenty of updates throughout known as Celebration at Deep Creek.brbrFrom the moment that you step inside this luxurious mountain home, you will be in awe. Walking through the foyer, you will enter the Great Room where you will be greeted with expansive cathedral ceilings, floor-to-ceiling windows, an impressive wood fireplace & an oversized Smart TV for movie nights in. Gleaming hardwood floors flow throughout the Great Room and Dining Area creating a clean, sharp look. Imagine sitting outside on the expansive deck enjoying lake views as you sip your morning coffee or enjoying a refreshing lake breeze as you barbecue in the afternoon.brbrThe main attraction on this level is the private indoor swimming pool (30’x14’). Colorful and artistically adorned, this is where your kids will want to spend most of their time! There will be lots of smiles and laughter as they splash and play in their very own heated pool year-round!brbrThe oversized kitchen is outfitted with stainless steel appliances and granite countertops. It offers two refrigerators, two ovens, and enough counter space to make whipping up a delicious meal for your family and friends a breeze!brbrAlso on the main level, you will find two bedrooms, both with Queen sized beds and TVs for your viewing pleasure. Together they both share the Jack-N-Jill bathroom.brbrThe fun continues upstairs in the loft area where you can challenge a friend to a competitive game of pool! There is also a two-player, table arcade machine with tons of games to keep you entertained. Here you will also find two of your Master Suites both of which feature King sized beds. Prominent features of both suites are the oversized Jacuzzi Tubs and private deck access, perfect for when you want some time alone to unwind.brbrDown in the lower-level Family Room, the kids will love watching movies on the large flat-screen TV or engaging in an exciting game of foosball. On this level, you will find your remaining four bedrooms; 2 Master Suites with King sized beds and 2 with Queen sized beds.brbrAll rooms are beautifully decorated in pleasing hues and recently received fresh coats of paint throughout. Furniture has also been carefully selected and recently updated to provide the highest of quality and comfort during your stay. Bathroom showers & baths updated in June 2025.brbrIn the winter, ski enthusiasts will love the proximity to Wisp's ski slopes. After spending a day snow tubing and tackling the ski slopes, an outdoor hot tub is waiting to soothe your tired muscles.brbrDuring the summer months, your dock slip is just a few steps away. You can spend sunny days swimming, fishing, and playing by the water. Bring a boat or rent one locally!brbrA wide variety of attractions are within a short drive. Everything from state parks and restaurants to kayak tours and whitewater rafting is at your fingertips.brbrCelebration at Deep Creek is truly a unique vacation home and one that you and your family will fall in love with. Choose this memory maker for your next Deep Creek vacation!brbrIf your rental is listed as having a Boat Dock as an amenity provided with this property, this is subject to weather conditions, water levels, and other natural factors.brbr*Please Note: A 4WD vehicle is required in winter months (November - March).

Bed

Bath

Sleeps

$590.62

/ Nightly

Private Vacation Home

Boxer Overlook | Lake Views, Hot Tub, Mountainside

Oakland, Maryland, United States

When you step through the doors of Boxer Overlook, you will immediately be taken in by the unparalleled elegance this home showcases. Ideally located in a quiet community, this 5 bedroom chalet is perfect for large or multi-family gatherings. Offering an open concept floor plan, this home showcases a harmonious flow. You will instantly fall in love with the Great Room which boasts expansive cathedral ceilings, an impressive wood fireplace, gleaming hardwood floors and beautiful furniture. This room also leads out onto your deck access where the spectacular lake and mountain views will captivate your attention. Equally astonishing is the state of the art kitchen which features gorgeous granite countertops and new updated appliances. Here you will find everything you need to create a gourmet meal or put together a simple breakfast. Enjoy family time together dining around the large dining table. For those that are looking for a quiet space to get away, the additional reading nook is the perfect place to escape with a favorite book. The main level also houses two of your bedrooms both which offer Queen Sized beds. The upper level Primary Suite is beautifully decorated to showcase a mountain theme and offers you a single jetted tub and private deck access. A great deal of fun will be had by all in the lower level Family Room where you can watch a favorite movie or play an exciting game of billiards with your friends. Here you will find your remaining two bedrooms, one with a Queen bed and the other with a Bunk and Duobunk beds. Fluffy comforters and the provided linens are extra reassurance that you will have a night of peaceful slumber. Located in the prestigious community of Mountainside, you and your family have access to the community amenities such as the basketball and tennis courts and the large pavilion. With very little road traffic, this is also a great neighborhood to enjoy a morning or evening stroll. Additional amenities of this home include Air Conditioning, High Speed & Wireless Internet, and the pet-friendly option to bring your furry friend. A short drive away you will find Wisp Resort and Deep Creek Lake State Park. Boxer Overlook is a true mountain gem and one that you will want to visit time and time again. Call today to plan your next mountain adventure.brbr*Please Note: A 4WD vehicle is required in winter months (November - March).brbrFor your convenience, this home offers free wifi.

Bed

Bath

Sleeps

$596.89

/ Nightly

Private Vacation Home

Lazy Days | Charming Lakefront Cottage

Oakland, Maryland, United States

Time to kick back, relax, and enjoy Lazy Days. This charming and charismatic lakefront home is the ideal choice for the small family getaway or a couple's retreat. brbrLocated on top of Wisp Mountain, you will love the close proximity to Lodestone Golf Course, ASCI (The Adventure Sports Center International, to the Wisp Resort and state parks).brbr Entering into the home through the kitchen and dining area, you will immediately feel the bright and airy feel of the home. Prepare delectable treats and meals in this fully stocked kitchen. Dine around the dining table in the dining nook or head out to your deck access and picnic outside. brbrThe main level also houses a full bath and the gorgeous Great Room which will quickly become the favorite gathering space for your family and friends. Large vaulted ceilings combine with an impressive stone fireplace to give you the feeling of extra space while the floor to ceiling windows of your deck access allow the perfect amount of sunlight to filter through. Your main floor bedroom has a wonderful king size bed and is beautifully decorated to flow with the soft ambience that flows throughout the home.brbr Your upper level houses 2 of your bedrooms (one with a king sized bed, one with a queen) and a full bath. Plush comfortable bedding and the provided clean linens will add to your comfort so that you can awaken refreshed and ready to start the day! Head to the lower level where you and your family can enjoy a game of bumper pool, watch a favorite movie on the flat screen TV or read a favorite book while curled up in front of the wood fireplace. Here you will find your laundry room, full bath, bonus room with 2 twin beds and your deck access.brbr Winding down a rock/ stair pathway, you will find your private dock slip. Spend your summer days swimming and splashing from your dock or bring your fishing gear for some quiet fishing time. Perfect location for catching some of Deep Creek Lake's best sunsets, you will love hanging out here each evening. Guests will also enjoy additional amenities such as unwinding in the steamy outdoor hot tub, connecting on the high speed and wireless internet, Air Conditioning or enjoying the use of the Deep Creek Fitness Pass. brbrLazy Days is the perfect definition of what you can experience when you choose to stay in this delightful home. Please call today for more information on reserving this special home.brbr For your convenience, this home offers free wifi.brbrIf your rental is listed as having a Boat Dock as an amenity provided with this property, this is subject to weather conditions, water levels, and other natural factors.

Bed

Bath

Sleeps

$1113.12

/ Nightly

Private Vacation Home

Stone Crest | Centrally Located, Fire Pit!

Oakland, Maryland, United States

Brimming with recent updates, Stone Crest is in the heart of Deep Creek Lake. It offers a convenient location, spacious layout, and great amenities.brbrBeautifully decorated, the main level features a wall of windows, cathedral ceilings, and a towering stone fireplace. Curling up in front of the crackling fire to watch TV will be a favorite way to spend lazy afternoons. Sliding doors open to the deck, so you can easily enjoy the scenic view too. Anyone who needs to stay in touch with work will appreciate the separate office space that is complete with a desk.brbrMealtime is a delight with two dining tables that each seat eight. There are three more stools at the breakfast bar as well. The kitchen is fully equipped, and you can make delicious food to share with family and friends.brbrThe main level primary suite is a restful haven where you can sink into the king bed to watch TV at bedtime. You will love the private bath that has an oversized jetted tub that offers total relaxation. Sliding doors give you access to the deck when you want to step out and survey the view.brbrUpstairs, there is a suite that is your own private retreat with a king bed and TV. You are sure to sleep well and wake up ready to experience new Deep Creek Lake adventures.brbrOn the lower level, the family room is set up for a fun evening at home! It has a pool table, TV, gas fireplace, and a second refrigerator.brbrThere are four bedrooms on the lower level. Decorated in soothing neutral tones, each one has a a queen bed and a TV.brbrIncredible outdoor living space allows you to truly savor the lakefront location. The expansive deck overlooks the lake and gives you a place to soak up some sunshine. Picnic tables give you a place to dine al fresco with boats cruising by in the background. The lower level deck is a spot where you can unwind on the swing or in the bubbling hot tub.brbrSpend lazy days at the dock swimming or fishing. You have your own boat slip so you can bring your own or rent one at a local marina. Your crew will love boating on sunny summer days. Take the kids tubing and follow it up with lunch at a lakefront restaurant. Spend evenings together around the fire pit under starry mountain skies.brbrWithin less than a mile, you will find several restaurants, the movie theater, nightlife, and a market. You only have to drive a few minutes further to find marinas, ziplines, shops, mini golf, and arcades.brbrWisp Resort is just six miles away, and they have tons of recreational opportunities. Skiing, snow tubing, golf, ziplines, disc golf, and a mountain coaster are just a few of the activity options.brbrChoose Stone Crest for your next Deep Creek Lake vacation! You can look forward to a fun and relaxing getaway from start to finish.brbrIf your rental is listed as having a Boat Dock as an amenity provided with this property, this is subject to weather conditions, water levels, and other natural factors.

Bed

Bath

Sleeps

$923.7

/ Nightly

Private Vacation Home

Stargazer | Phenomenal Lakefront Views!

Oakland, Maryland, United States

For the chance to stay in one of Deep Creek's most desired vacation homes, book a relaxing escape at Stargazer where peaceful days and starry nights are guaranteed. Mesmerizing from the second that you step inside, prepare to be swept away by the extraordinary lake views that greet you from the large expansive windows. Elegant furnishings, glistening dark hardwood floors, and vaulted cathedral ceilings give the Great Room a majestic feel while the double sided fireplace ensures comfort and warmth whether you are snuggling on the couch or enjoying a fabulous feast in the dining room. Designed for a true gourmet chef, this immaculate state of the art kitchen has everything you need to create delicious family meals. The covered outdoor porch has updated and stylish outdoor furnishings and will be the perfect place for you to wind down in the evenings.brbr The kids will love hanging out in the lower level Family Room where they can challenge each other to a friendly game of foosball or watch their favorite movie on the large flat screen TV. Each bedroom is superbly furnished and showcases luxury linens and comforters. You will rest peacefully each night and awaken to a new day's adventure! This outstanding elite home also features desirable amenities such as high speed & wireless internet, Air Conditioning, a High Efficiency Washer & Dryer, as well as unlimited long distance calling.brbr Step outside and continue to experience a true Deep Creek experience with this premiere level lakefront. A grassy lawn leads down to your easy walk in lake access as well as your very own private dock! Summer days and many unforgettable memories will be spent swimming, fishing and playing in the water! Bring your own kayaks or rent them locally as this quiet area of the lake is an ideal spot for taking off for a morning trip down the shoreline. After a hard day of living the lake life, come home and retreat to the steamy outdoor hot tub for total rest and relaxation! Just a short drive from State Parks, Wisp Resort and area shopping and dining, the location of this home offers complete convenience to you and your guests. Stargazer is a phenomenal vacation home that will easily become your new family favorite. Make your Deep Creek dream a reality by calling today to plan your future stay in this one of kind lakefront home!brbr For your convenience, this home offers free wifi.brbrIf your rental is listed as having a Boat Dock as an amenity provided with this property, this is subject to weather conditions, water levels, and other natural factors.

Bed

Bath

Sleeps

$1433.06

/ Nightly

Private Vacation Home

Champagne Taste | Level, Lakefront, Private Dock

Oakland, Maryland, United States

Looking for the finest, most preeminent home to pamper you while on vacation This stunning and impressive home has so many unique and elegant features, it will let you heartbroken when it is time to depart. brbrFrom the moment you enter, you will be in awe of how delicately detailed every room has been prepared. This house offers a fully equipped, gourmet kitchen which should meet the standards of the chef in the bunch. The great room has stunning hardwood floors, 50 plasma TV and top of the line furniture which are all inviting for you to relax and unwind your day. brbrYou could also make your way to the outdoor hot tub which is situated on a raised platform with privacy walls, so you can breakaway from everyday life with no interruptions. If you need to refresh and rejuvenate yourself, step into one of the suites and take a hot, relaxing European Shower! If you are the fortunate person in the bunch, your primary suite is not only equipped with a European shower for two, but also has a Jacuzzi whirlpool tub with a waterfall and adjustable LED lighting, which is perfect for setting the mood. brbrOnce you are refreshed and ready for excitement, make you way upstairs for an exciting game of pool or walk to the lakefront and gaze at the stars of Deep Creek. brbrWith so many features, no matter your personality, preferences, or needs are, you will get all of these satisfying features with one visit to Champagne Taste. brbrFor your convenience, this home offers free wifi.brbrIf your rental is listed as having a Boat Dock as an amenity provided with this property, this is subject to weather conditions, water levels, and other natural factors.

Bed

Bath

Sleeps

$537.57

/ Nightly

Private Vacation Home

Lake House | Close to Swallow Falls State Park

Oakland, Maryland, United States

Offering everything you need for a fun and relaxing vacation, Lake House is the perfect place to make your Deep Creek Lake vacation memories!brbr The spacious main level is highlighted by gleaming hardwood floors, cathedral ceilings and a towering wall of windows that reveal lake views through the trees. Everyone will be drawn to gather around the warmth of the stone fireplace as you chat about your plans for the day or curl up to watch your favorite TV show.brbr Whip up homestyle meals in the well-equipped kitchen before settling down at the dining table to enjoy quality time with family and friends. Deck access makes eating outdoors and afternoon barbecues a breeze.brbr You are sure to get a good night's sleep in the main level primary suite. Furnished with a king bed and a TV, this is your own personal haven that is complete with deck access and lake views.brbr Grab a book from the shelves in the great room, and head to the upper level loft. The double futon is the perfect spot to do a little reading. There is also a bedroom with a double futon, queen bed and TV along with a second bedroom with a queen bed and TV. Each one is furnished with your comfort in mind.brbr The lower level family room will keep you entertained with you want to spend a fun evening at home. Watch an old movie on TV or challenge a friend to a little competition at the pool table. Kids in your group will love the bedroom with two twins and a duobunk. It is there own hang-out spot complete with a TV.brbr Everyone will love the exceptional outdoor space. You can unwind on the expansive deck or take a short stroll down the path to your private dock. Bring your boat or rent one locally to explore the lake and its quiet coves. Summer days are best spent swimming and fishing before getting together around the outdoor fire pit for s'mores as the sun starts to set. brbr Conveniently located, you are within just a few minutes from Swallow Falls State Park - one of the area's most popular attractions. A short drive will also take you to restaurants, the movie theater, mini golf and much more.brbr When winter weather arrives, Wisp Resort is within a fifteen-minute drive. You can ski, snowboard, snow tube and ice skate and then return home to the cozy fireplace. During the warmer months, they offer a wide variety of activities for all ages. Atop the mountain, you can experience whitewater thrills at the Adventure Sports Center International.brbr Make your next vacation one to remember when you choose Lake House as your destination at Deep Creek Lake!brbr For your convenience, this home offers free wifi.brbrIf your rental is listed as having a Boat Dock as an amenity provided with this property, this is subject to weather conditions, water levels, and other natural factors.

Bed

Bath

Sleeps

$808.1

/ Nightly

Private Vacation Home

Claralea Lodge | Secluded, Lakefront, Private Dock

Oakland, Maryland, United States

Surround yourself with nature in this majestic log home. Four suites make it an excellent choice for couples as well as family gatherings.brbr On the entry level, hardwood floors, cathedral ceilings and large windows adorn the great room, and the stone fireplace and stylish furnishings accent the warmth of these rooms. An open layout makes it easy to enjoy the company of family and friends when you are making a home cooked meal in the well-equipped kitchen. The island seats three adding to the seating for twelve in the dining area. The long wooden table is sure to be the site of lots of good conversations by the fire. With the deck just off of the great room, your living space is instantly expanded. Grill out on summer evenings or sip your coffee on crisp fall mornings. No matter what the time of year, the sounds of Mother Nature will be all around you.brbr The main level primary suite is truly inviting with well-chosen decor that evokes a mountain feel. Catch up on your rest in the king bed or watch a little TV before getting some shut eye. This is a great spot to refresh before another day of fun at Deep Creek Lake.brbr Upstairs, you will find two more suites. Each offers a queen bed, TV, and DVD player. Whether you need a cat nap or just a little quiet time, you will appreciate the privacy on this level.brbr The lower level family room was designed with quality time in mind. Enjoy the ambiance of the cozy gas fireplace as you watch your favorite movie, play cards at the game table, or challenge a friend to air hockey. The kids in your crew will love the bedroom with two bunkbeds. Rounding out the sleeping quarters is another bedroom with a queen that also has access to the hall bath.brbr When the stars come out, soak in the bubbling hot tub while enjoying the beautiful views of the lake and surrounding woodland. The private dock sits in a quiet cove making swimming pleasurable and fishing fantastic. Gather the kids and break out the s'mores for story time around the outdoor fire pit.brbr Tucked beneath large pines and conveniently located only a couple miles from the heart of Deep Creek Lake, you can enjoy the best of the area without spending a lot of time behind the wheel. Activities such as white water rafting, boat rentals, restaurants, Wisp Ski Resort and golf are just a short drive away.brbr Make Claralea Lodge your choice for Deep Creek lodging, and look forward to a fun and relaxing experience with your favorite people.brbr For your convenience, this home offers free wifi.brbrbrIf your rental is listed as having a Boat Dock as an amenity provided with this property, this is subject to weather conditions, water levels, and other natural factors.

Bed

Bath

Sleeps

$699.16

/ Nightly

Private Vacation Home

Highland Retreat | Incredible Lakefront, Deck

Oakland, Maryland, United States

Mountain memories start here! Highland Retreat is a marvelous 5 bedroom lakefront home that combines elegant decor with a bevy of fun amenities.brbr Located on the western end of the lake, you and your guests will love cooling off on hot summer days by swimming and splashing from your very own private dock. brbrSpacious cathedral ceilings, large windows and a spectacular stone fireplace create the perfect warm ambience for gathering in the Great Room. Enjoy a game of billiards in the lower level or take a relaxing soak in the steamy outdoor hot tub.brbr Evenings will be enjoyed at the water's edge as you hang out around the outdoor fire pit making s'mores and sharing stories of the days adventures. brbrEnjoy peaceful morning strolls around the hiking trail that loops around the lake's edge. Conveniently located near area golfing and hiking and biking, this home also offers enough seclusion to give you the privacy you seek. Call today to begin planning your next Deep Creek stay in the dazzling home known as Highland Retreat. brbrFor your convenience, this home offers free wifi.brbrIf your rental is listed as having a Boat Dock as an amenity provided with this property, this is subject to weather conditions, water levels, and other natural factors.

Bed

Bath

Sleeps

$1051.56

/ Nightly

Private Vacation Home

La Bella Vita | Amazing Lake Views, Upscale Decor

Oakland, Maryland, United States

True to its name, the good life awaits at La Bella Vita! This stunning home promises an exceptional Deep Creek Lake vacation for your family and friends. With amazing lake views from almost every room and upscale decor throughout, this will quickly become a favorite spot to get away from it all. Attention to detail is apparent inside and out. There is even an Electronic Vehicle (EV) Charging Station that will give you a fast charge when you're ready to explore the area. Upon entering the main level, your eyes will be immediately drawn to the wall of floor-to-ceiling windows that reveal the lake and surrounding mountains. Lots of natural light and cathedral ceilings give a bright and airy feel to the open floorplan that lends itself to entertaining. The spacious great room will be a popular gathering spot with the stone fireplace as its focal point. You can curl up on the sofa or in one of the cozy armchairs to watch a little TV before retiring for the night. The chefs in your group will love the well-equipped kitchen that offers everything you need to make your family’s best-loved dishes. With seating for six at the breakfast bar and eight at the table, you can comfortably share meals with scenic views as your backdrop. Doors lead to the deck, where you can cook out on a warm summer evening and dine al fresco. After a long day of swimming in the lake or hitting the slopes, you can get a good night’s sleep in the main level master suite. You will love stargazing from your private deck before watching TV from the roomy king bed. When you awake, striking views will inspire you to seize the day and make the most of your time at Deep Creek. The second main level master suite is a private haven that is furnished with a queen bed and TV. It will be easy to catch up on your sleep after a leisurely day of lake activities. Upstairs, the loft expands your living space and has one of the best views in the house. You can challenge a friend to a game of shuffleboard or rack ‘em up on the pool table while you watch your home-team on the wall-mounted flatscreen. A spiral staircase leads you up to another level that is a unique spot where you will feel instantly relaxed. Overlooking the lake, you will feel like you are on top of the world when you curl up on the cushioned bench seats with a good book. Offering private decks where you can savor the scenery, two upper level master suites with TVs, one with a king bed and one with a queen, give you a separate space to unwind. Early birds will appreciate dazzling sunrise views each morning – the perfect accompaniment to a warm cup of coffee. Head downstairs to the spacious media room to screen your favorite movie on the massive 85 inch TV. Handsome leather furnishings and a stone fireplace combine to create a warm and inviting ambiance. When you feel like a little friendly competition, take a seat at the poker table that is complete with cards and chips. You can keep snacks and drinks handy at the wet bar with a mini fridge and Keurig. A separate den with a TV and daybed with a trundle gives you an additional sleeping space for extra guests. After an entertaining evening in, a queen bed and TV are waiting for you in the lower level bedroom. The outdoor living spaces truly shine at La Bella Vita. Multiple decks give you a variety of vantage points to take in the landscape that will change with each season. Plus, a screened porch with wicker furniture ensures you can enjoy fresh mountain air no matter what the weather. When you need to soothe tired muscles after hiking or cross country skiing, soak in the warmth of the bubbling outdoor hot tub. Crystals are available for your use that turn it into an aroma therapy hot tub! Centrally located, the best of Deep Creek Lake is within a short drive. You can go fishing at the community dock or head to the state park’s sandy beach to swim, kayak or paddleboard. A five to ten-minute drive will take you to favorite restaurants, Wisp Resort, the Adventure Sports Center, shops, mini-golf and much more. Community tennis and basketball courts add to your options for activities too. When you are seeking a vacation home that is beyond compare, choose La Bella Vita for a special experience with your favorite people.brbr*Please Note: A 4WD vehicle is required in winter months (November - March).brbrLa Bella Vita offers a membership to the Community Aquatic Recreation Complex (CARC). You can enjoy the indoor pool and fitness facilities during your stay. If your rental is listed as having a Boat Dock as an amenity provided with this property, this is subject to weather conditions, water levels, and other natural factors.

Bed

Bath

Sleeps

$292.5

/ Nightly

Private Vacation Home

Home Sweet Cabin | Hot Tub, Multiple Game Tables!

Oakland, Maryland, United States

Experience the ultimate mountain getaway at Home Sweet Cabin, a charismatic vacation rental nestled in a peaceful, private cove. This charming mountain home features expansive wooden cathedral ceilings and a stone fireplace, offering the perfect backdrop for bonding with family and friends.brbrThe open-concept floor plan allows you to entertain effortlessly while preparing gourmet meals in the well-stocked kitchen. Designed for comfort, the main level hosts two cozy bedrooms — one with a queen bed and another with a twin/double combo — all outfitted with luxury linens and towels for a seamless stay.brbrThe upper level is a true sanctuary, featuring a private primary Suite with a King bed and a charming loft with a twin bed that kids will love. For those seeking entertainment, the lower-level family room is a hub of fun, offering friendly competition with foosball, air hockey, and ping-pong. A fourth private bedroom with a queen bed is also located on this level, and every bedroom in the home includes a flat-screen TV for your viewing pleasure.brbrStep outside to breathe in the fresh mountain air from the expansive wraparound deck or melt away your worries in the soothing outdoor hot tub. Ideally located for year-round adventure, Home Sweet Cabin is just a short drive from Wisp Resort for skiing and the charming town of Oakland for antique shopping and local museums. Guests visiting for a full week in the summer also receive a State Park pass, granting access to the breathtaking beauty of Swallow Falls and Deep Creek Lake State Park.brbrEquipped with free wifi and modern amenities, this home is the perfect home base for your next Deep Creek Lake vacation. Book your stay at Home Sweet Cabin today and discover the perfect blend of relaxation and adventure.brbr*Please Note: A 4WD vehicle is required during winter months (November - March). This home is equipped with exterior security cameras.

Bed

Bath

Sleeps

$446.42

/ Nightly

Private Vacation Home

Mountain House | Pet Friendly, Dock, Great Views!

Oakland, Maryland, United States

Enjoy the feeling of rustic mountain living in this cedar chalet. Cozy and inviting, this home is perfect for accommodating the extended family or group of friends.brbr Wood-lined walls, cathedral ceilings and a beautiful stone fireplace greet you upon entering the main level. The open floorplan lends itself to lively get-togethers with your favorite people. Lots of natural light pours in through the wall of windows giving this space an airy feel. Comfortable furnishings in the great room will beckon you to curl up in front of a crackling fire as you watch your favorite movie on the Blu Ray DVD play. Surround sound is an added bonus!brbr Cooking for your crew is easy in the well-equipped kitchen. Seating at the breakfast bar and dining table gives you plenty of room to share meals and linger for board games after the dishes are cleared. Sliding doors lead to the deck when you want to grill and eat outdoors on a sunny summer day.brbr The main level offers two bedrooms each of which is outfitted with a TV, DVD player and AC unit to keep you cool. On has two twins and the other has a queen bed. Both are furnished with your comfort in mind.brbr Upstairs, you will find another bedroom with a queen, TV, Blu Ray DVD player and AC unit. This is a separate space that is perfect for afternoon catnaps.brbr Kick-back and watch the big game in the lower level family room that has a TV, Blu Ray DVD player, surround sound and wet bar. A queen sleep sofa gives you additional space for your guests. A bedroom with two bunkbeds and another with a queen bed round out the sleeping quarters.brbr Surrounded by towering trees, the wrap-around deck is ideal for savoring the serenity of nature. It is a place that encourages you to relax and leave your worries behind.brbr Your lakefront area with steps descending to the waters edge and private dock is directly across the road. Bring your boat or rent one locally to head out for a day on the lake. When you return, you can spend time swimming, fishing or kayaking.brbr Close to area activities, it is easy to get out and explore the Deep Creek Lake area. Restaurants, mini golf, coffee shops, arcades and marinas are within a short drive. Wisp Resort is where you will find four seasons of fun. Offering everything from a mountain coaster and ziplines to ski slopes and snow tubing, there is no shortage of fun! Atop the mountain, a whitewater course delivers thrilling raft rides through the rapids! No trip to the lake would be complete without visiting our state parks. Thousands of acres of public land give you the opportunity to hike, mountain bike, canoe, cross country ski and much more!brbr Make Mountain House your vacation destination, and look forward to making lasting vacation memories in a special place.brbr For your convenience, this home offers free wifi.brbrIf your rental is listed as having a Boat Dock as an amenity provided with this property, this is subject to weather conditions, water levels, and other natural factors.

Bed

Bath

Sleeps

$700.77

/ Nightly

Private Vacation Home

All About the View | Lakefront, Awe-Inspiring View

Oakland, Maryland, United States

All About the View is a remarkable lakefront home that encompasses all the qualities that make a vacation truly great. Its unique design, desirable amenities and ideal location combine to create the perfect venue for a vacation with family and friends. Gathering together in the Great Room will easily become a favorite activity. Large vaulted ceilings and gleaming hardwood floors create a bright and airy ambience but it is the floor to ceiling windows that reveal stunning lake views that will keep you in awe. A true chef's dream, the gourmet kitchen boasts gorgeous granite countertops, stainless steel appliance and additional island space. Spend family time dining around the dining table as the conversation swirls around the amazing lake views and the one of kind chandelier decor!brbrYour first bedroom with a Queen Size bed is on the main level and offers partial lake views. In addition to a bath with large shower stall, you will also find your laundry area with a full size washer and dryer.brbrSpend some quiet time in the upper level loft sitting area as you take in the mesmerizing lake views. The first bedroom on this level has a queen bed, private bath, and full lake views. A king-size bed occupies the 2nd bedroom on this level. Your guests will enjoy partial lake views and a private entrance to the bath shared with the loft.brbrThe big game can be enjoyed in the lower level Family Room on the 42 flat screen TV. Convenient amenities on this level include the wet bar with under the counter fridge, coffee maker and microwave. Retire to the Primary Suite with a King size bed on this level and again come to realize why this home is aptly named All About the View. The in-room TV and CD/iPod player are wonderful additions.brbrOffering so many amenities, your guests will enjoy luxuries such as Air Conditioning, I-Home, High Speed Wireless Internet, and much more!brbrYour private dock allows you to bring a boat or rent one locally and dock it throughout your stay! Not only will you enjoy swimming and fishing from the lakefront but this area is well known for its exquisite sunrises and sunsets!brbrYou'll find a huge range of activities to enjoy nearby, from skiing and hiking to dining, shopping, rafting and much more. All About the View is the best choice for an unforgettable Deep Creek Lake vacation! Call today to plan your next Deep Creek adventure!brbrFor your convenience, this home offers free wifi.brbrIf your rental is listed as having a Boat Dock as an amenity provided with this property, this is subject to weather conditions, water levels, and other natural factors.

4

Bed

4

Bath

10

Sleeps

Vacation Home Rentals By Owner In Oakland, MD

$699.25

$475.32

$827.39

$481.39

$496.66

$372.97

$370.72

$1722.31

$590.62

$596.89

$1113.12

$923.7

$1433.06

$537.57

$808.1

$699.16

$1051.56

$292.5

$446.42

$700.77

Rent a place that suits your needs

Most popular vacation rentals in Oakland

$859.79

$962.54

$930.25

$907.91

$897.05

$863.84

$863.79

$805.26

$823.10

$827.39

Most Popular Cities in Maryland