Home Vacation Home Rentals By Owner In Oakland, MD

Showing 20 Of 363 Vacation Rentals
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Exceptional(5)

$985.28

/ Nightly
Private Vacation Home

Amazing Flat Lakefront Home with Hot Tub + Fire Pit!

Oakland, Maryland, United States

Lakefront vacations have never been sweeter than at In the Groove! This beautiful *NEW* construction was built for full-family enjoyment in all four seasons, with a large level lakefront, with 300-foot-long play space from the home to the water (great for kids!), lake-facing fire-pit, and private dock slip. The home is located along a private, no-wake cove making the waters here ideal for swimming, kayaking, fishing, and boating.brbrInside the home, you'll find amenities galore! In the main level great room, enjoy the breathtaking design of the vaulted knotty pine ceiling, floor-to-ceiling windows, and oversized sliding glass doors opening out to the spacious wrap-around deck with gorgeous lake views. The gas fireplace, plush sofas, and large 75 smart TV with cable, and custom-built 10-foot dining table round out the space with all the amenities you need to keep everyone thoroughly entertained. brbrThe kitchen is a chef's-delight, stocked full of high-end appliances and cookware, including a fully-stocked appliance closet with a crockpot, insta-pot, blender, and so much more. The granite counters, luxury Viking brand-appliances, dual oven, glass cooktop, large kitchen island, farmhouse sink and dual-temperature wine fridge will make you excited to whip up something tasty. brbrElsewhere on the main level, you'll find the primary master suite with king bed, half-bath with whiskey barrel sink, two storage closets and a mudroom you'll just love, complete with a washer and dryer, space for your ski gear and oversized storage rack. Every bedroom in the house features large TCL Roku Smart TVs and super comfortable DreamCloud mattresses. Plus: the Wifi signal throughout the house is strong with extenders built-in to the house to help ensure a strong signal. All Roku Smart TVs are hardwired to maximize internet speed, performance, reliability, and reduce the demand on Wi-Fi. You'll have no problem attending work zoom calls or streaming all your favorite shows! These amenities make it easy to settle in and feel perfectly at home.brbrUpstairs, there is a large loft overlooking the great room, featuring picturesque views of the home's lakefront, as well as a desk for remote-work and accent chairs, perfect for curling up with a good book. Both upper level bedrooms are master suites with comfortable, just-like-home atmospheres, king beds, and attached full bathrooms.brbrDescending the stairs to the home's lower level, enjoy a space built for entertainment! This large recreation room includes a full-size sectional, large Smart TV, gas fireplace, wet-bar with full-size fridge, custom-built whiskey barrel cocktail table, full-size shuffleboard table, and foosball table. The two nearby bedrooms share a full bathroom between them, which includes a combination shower/tub. In one bedroom, you'll find a queen bed and in the other you'll find two duo-bunks, custom-built beds with full mattresses on the bottom and twin mattresses on top. Kids love this space! brbrWithout question, you'll find yourself drawn outside to enjoy the incredible amenities and spectacular lakefront view. On the main deck, enjoy plentiful outdoor seating with large outdoor dining table, high-end Adirondack loungers, and gas grill. Down on the lower level patio, take a soak in the lake-facing hot tub, play cards out on the picnic table, or curl up with coffee on the outdoor sectional. For starry nights, grab some marshmallows for s'mores at the fire-pit, featuring convenient cooking grate and comfortable Adirondack loungers. Tell the kids to pack a soccer ball or two. The large backyard is perfect for running around! brbrLocated near the center of Deep Creek Lake, In the Groove offers the perfect vantage for enjoying all that Deep Creek Lake has to offer. Hop in the car and explore a world of activities from restaurants, outdoor attractions, marinas, shopping, and more. The popular lakefront Harbor Bar and Honi Honi Bar, as well as the local movie theater and the 24-hour market, Arrowhead, are all located within a 2 minute drive of the house. Head south and visit the popular Pawn Run Bar, Deep Creek Lake's oldest bar or schedule a trail ride adventure at Circle R Ranch.brbrWisp Resort is one destination you won't want to miss, no matter the season! Skiing, snowboarding, snow tubing, golf, zip-lining, and white water rafting are just a few of the activities they offer throughout our four beautiful seasons. brbrIn the Groove is a vacation destination onto itself, bringing together the magic of the lake with all the rich comforts of a luxury retreat. Your family is sure to love it!brbrSleeping arrangements: 3 king bed, 1 queen, 2 duo bunks (full beds on bottom; twin beds on top), 1 queen sleeper sofabrbr* 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 5

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Bath 4

Bath

Sleep 14

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Exceptional(12)

$328.11

/ Nightly
Private Vacation Home

Wooded Bliss | Boat Slip, Firepit, Lake Access!

Oakland, Maryland, United States

Treat yourself to a stay at Wooded Bliss, a spacious home in a private natural setting where you'll enjoy your own boat slip and plenty of relaxation when you aren't out on the lake having fun!brbrThe roomy main level is highlighted by a stunning floor-to-ceiling stone fireplace that will keep you cozy throughout cooler nights or winter days. Gather in the great room to watch TV by the crackling fire after a day of hiking nearby Swallow Falls State Park or Skiing over at Wisp Resort. A wall of windows reveals beautiful scenery, and doors open to the deck so that you can thoroughly enjoy your surroundings.brbrFully equipped, the eat-in kitchen has all the essentials to keep your crew refueled and adequate space for everyone to gather around and lend a hand with cooking or cleanup! Share meals at the dining table that has a seat for everyone or head out to the deck to enjoy a bbq feast on the gas grill.brbrThere are two bedrooms on the main level, and each with plush mattresses and tasteful linens to ensure a restful sleep. There is a full bathroom on this floor as well.brbrUpstairs, the loft has a large sectional sofa where you can grab a seat to watch the latest blockbuster hit or the big game. There are two more bedrooms on this level along with a full bath that has a shower stall and soaking tub.brbrOutside, you can sip your coffee each morning on the deck as you listen to the sounds of nature and soak in the wooded scenery hoping to catch a glimse of the local wildlife.brbrA path through the trees leads to your lake access where your boat slip awaits. Bring your own boat or rent one at a nearby marina to spend the day exploring the lake’s miles of shoreline. When you return, get together at the fire pit for s’mores under the stars.brbrOne of the area’s best-loved attractions, Swallow Falls State Park, is less than four miles from your doorstep. Miles of hiking trails wind through pristine forests leading you to three picturesque waterfalls.brbrWooded Bliss is less than five miles from the closest restaurants and shops as well as the movie theater.brbrA fifteen-minute drive will take you to Wisp Resort where you can experience tons of fun outdoor activities. Known for year-round recreation, they offer golf, skiing, snow tubing, ziplines, disc golf, and a thrilling mountain coaster.brbrChoose Wooded Bliss for your next Deep Creek Lake vacation and look forward to a truly memorable 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 3

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Bath 2

Bath

Sleep 10

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Exceptional(5)

$1078.83

/ Nightly
Private Vacation Home

Deep Creek Escape w/ Dock, Hot Tub & Views

Oakland, Maryland, United States

Name: Jewel in Paradise | Bedrooms: 5 | Bathrooms: 4 | Sleeps: 14 | Access: Lake Front | Pets Not Permitted | MUST BE 24+ YEARS TO RENT | Free WIFI ProvidedbrbrDESCRIPTION:brThis home couldn’t be more properly named. A Jewel in Paradise is truly a dream lakefront escape. This stunning blue home, peeking out between the trees will welcome you in with the warmth of comfy furnishings, perfectly sized, open concept kitchen/living/dining areas, a spacious 2-level deck, and more. On clear nights, relax on the private dock or the deck looking at the starry night sky. What better way to unwind after a day on the lake in the area than in the bubbles of the hot tub or around the fire. Gather in the great room or the lower den for movie marathons and quality family/friend time or break off into different rooms for some personal time. Deep Creek Lake State Park, the four season Wisp Resort, and many other lake area adventures are just minutes away. You’ll never run out of things to keep you busy and you really will feel like you are in paradise here. So hurry and book you stay to escape to the lake today!brbrACCESS DETAILS:brThis property comes with private lake access and a private dock slip located at property. Please note that docks are only guaranteed from Memorial Day through Labor Day.brbrCOMMUNITY/AREA DETAILS:brLocated in the Paradise Point Community at Deep Creek Lake.brbrLAYOUT DETAILS:brMain Level:br- Kitchenbr- Living Areabr- Dining Areabr- Powder Roombr- Bedroom (Suite): Queen Bed, Attached Full Bath with Showerbr- LaundrybrbrUpper Level:br- Landing Areabr- Bedroom (Suite): King Bed, Sitting Area, Attached Full Bath with Massive Shower and Separate TubbrbrLower Level:br- Den Areabr- Bedroom: Queen Bedbr- Bedroom: Full Bunk Bedbr- Full Bath with Shower/Tubbr- Bedroom (Suite): King Bed, Attached Full Bath with ShowerbrbrDISCLAIMERS: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 5

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Bath 4

Bath

Sleep 14

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Exceptional(1)

$496.77

/ Nightly
Private Vacation Home

Family-Friendly Private Cabin with Hot Tub + Fire Pit

Oakland, Maryland, United States

Welcome to Blooming Rose Cabin, your perfect retreat nestled in the heart of the mountains. This charming log cabin offers a cozy, rustic escape with its warm wood interior and inviting mountain aesthetic. As you approach the cabin, you'll be greeted by a spacious front porch, complete with a swinging bench and comfortable seating. It's the ideal spot to savor your morning coffee while taking in the serene, private wooded setting.brbrThe backyard is a haven for families, featuring a playground for kids, lush green grass, and ample space for running and playing. For the adults, the outdoor amenities include a fire pit, a hot tub for relaxing under the stars, and corn hole boards for some friendly competition. You'll also find two grills—one gas and one charcoal—perfect for cooking up delicious meals.brbrInside, the modern kitchen is well-stocked with everything you need to prepare a home-cooked feast. The cabin boasts five comfortable bedrooms, ensuring plenty of space for everyone to unwind and recharge.brbrLocated just a stone's throw from Swallow Falls State Park, Blooming Rose Cabin offers easy access to Maryland's largest waterfall and a variety of hiking trails. Whether you're exploring the great outdoors or simply enjoying the comforts of this beautifully appointed cabin, Blooming Rose Cabin is the perfect home base for your mountain adventure.brbrSleeping Arrangements: 1 king, 2 queen, 1 queen sleeper sofa in the living room brbrDog Friendly Notice: Maximum of two dogs per reservations. A $175/non-refundable fee will be added for each dog (not included in original rental price). 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 3

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Bath 3

Bath

Sleep 8

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Exceptional(13)

$356.08

/ Nightly
Private Vacation Home

Meant to Be | Pet Friendly + Serene Wooded Views & Fire Pit!

Oakland, Maryland, United States

Choose Meant to Be and you are destined to have a truly memorable Deep Creek Lake vacation! Surrounded by trees, this dog friendly getaway is off-the-beaten-path yet still within a short drive from favorite activities. brbr The spacious main level has warm, wood accents, hardwood floors, and charming mountain decor. High ceilings and lots of natural light create a welcoming ambiance in the great room. You won't hesitate to sink into comfy furnishings in front of a crackling fire when you are ready to unwind. brbr Fully equipped, the kitchen has everything you need to make homestyle meals to please your crew. You can eat together at the dining table, and there is additional seating at the breakfast bar. Great food is sure to be accompanied by good conversation and lots of laughs. Doors open to the deck, so cookouts are convenient too. brbr After a day filled with hiking, swimming, or skiing, retire to the main level bedroom with a queen bed. It is decorated with a good night's sleep in mind. You will wake up refreshed and ready to explore the area. brbr Upstairs, the primary suite is a private haven where you can enjoy a little quiet time. Furnished with a queen bed and a TV, it is a great place to unwind at bedtime. brbr The lower level family room adds to your living space. It is outfitted with a TV and has a daybed with a twin trundle that can accommodate any extra guests you may have. There is also a bedroom with two twin beds on this floor. It has a sliding door that allows you to get some fresh mountain air any time you please. brbr Meant to Be offers wonderful outdoor space with plenty of room for your pup or kids to play. Enjoy dining outdoors on the larger of the two decks, or relax on the covered deck, perfect for any weather. Unwind in the private hot tub or gather around the fire pit—ideal for s’mores, stargazing, and making memories. This property also includes an EV charger, making it convenient for guests with electric vehicles.brbr Swallow Falls State Park is less than five miles from your doorstep. This is one of the area's best-loved attractions. Three stunning waterfalls make the perfect backdrop for your photos. Scenic hiking trails wind through the pristine forest and wildlife is abundant. brbr A ten to fifteen-minute drive takes you to restaurants, shops, mini golf, and more. Stop by a local marina to rent a boat for the day, and experience on the water fun! It is one of the best ways to see the sights. brbr Wisp Resort is well known for year-round adventures. There is something for every age and interest. Skiing, golf, snow tubing, ziplines, and a mountain coaster are just a few ways they will keep you entertained. brbr When you are in the mood for a beach day, head to Deep Creek Lake State Park. They have a sandy beach for swimming, picnic tables in the shade, several playgrounds, and kayak and paddleboard rentals. brbr Meant to Be gives you a valued chance to unwind, unplug, and uplift your spirit! Plan your next trip to Deep Creek Lake today! brbr For your convenience, this home offers free wifi. Please note that this home has exterior security cameras.
Bed 3

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Bath 3

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Sleep 8

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Exceptional(10)

$821.67

/ Nightly
Private Vacation Home

Loch Nest | Lakefront, Private Dock, Dog Friendly!

Oakland, Maryland, United States

This stunning chalet offers a prime lakefront location that you can enjoy with your entire family – including your pup! brStep inside the spacious main level where cathedral ceilings, wood accents, and a wall of windows create a welcoming atmosphere. Grab a seat on the massive sectional sofa in the great room to watch TV or unwind after a day on the water. On crips mountain nights, the wood burning fireplace will keep your crew cozy. brYou will love the open layout that makes it easy to spend quality time together. Beautifully updated, the kitchen has a large center island with seating, a gas range, and everything you need to make delicious meals. When it is time to eat, sit together at the table for great food and even better conversation. Doors open to the deck making cookouts a breeze.  brOffering access to the deck, the main level primary suite is your own private hideaway. It is furnished with a king bed and a TV. The private bath has a lovely tile shower along with a dual sink vanity. brUpstairs, the loft is a quiet spot where you can curl up with a book or use the desk to catch up on some work. There are two well-appointed suites on this level. Each is decorated with a good night’s sleep in mind. brFun for everyone comes easy in the lower-level family room. Play a game of pool or sink into comfy furnishings for a little TV time. You can keep your drinks cold and close by at the bar with a mini fridge. The gas fireplace adds the perfect ambiance for a leisurely evening at home. brThere is a roomy suite on the lower level along with a bedroom that is ideal for the kids in your group. Both have access to the deck. brExceptional outdoor living space will be a true highlight of your vacation. Two levels of decks give everyone room to spread out and enjoy the scenery. The screened porch is a fantastic bonus. It’s the best spot to savor your coffee in the morning as you make plans for the day.  brYou can’t beat staying lakefront with a private dock! Loch Nest has a platform with a swing where you can keep your gear while you swim, fish, kayak, or canoe. Bring your boat or rent one at a nearby marina to explore the lake’s miles of shoreline.  brWithin less than five miles, you will find Lodestone Golf Course, white water rafting at the Adventure Sports Center, and lots of outdoor recreation at Wisp Resort. Wisp is home to golf, skiing, snow tubing, ziplines, a mountain coaster, disc golf, and more! Restaurants, shops, mini golf, boat rentals, and more are within a ten-minute drive.  brLook no further - you have found the ultimate Deep Creek Lake vacation destination for fun, relaxation, and recreation. Reserve Loch Nest today! brbrPlease note that this home has exterior security cameras.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 5

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Bath 5

Bath

Sleep 14

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Exceptional(6)

$1384.59

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Private Vacation Home

Chic Lake Stay w/ Pool, Dock & Fireplaces

Oakland, Maryland, United States

Name: The Bear Necessities | Bedrooms: 5 | Bathrooms: 5.5 | Sleeps: 14 | Access: Lake Front | Pets Not Permitted | MUST BE 28+ YEARS TO RENT | Free WIFI ProvidedbrbrbrDESCRIPTION:brNestled on the shores of Deep Creek Lake, The Bear Necessities offers everything you’d ever need for a perfect vacation! Enter this stunning modern home to be greeted with the stunning waterfall feature in the foyer. Floor to ceiling windows in the great room and kitchen flood the home with natural light and make you feel like you’re staying in a magical tree house. The long open concept main level creates the perfect atmosphere for entertaining and coming together. The unique layout starts you out at the top of the home, with three total levels of living space as you work your way down. The indoor heated pool features a unique horse-shoe design that gets deeper as you swim around! In addition to the pool, you can gather in the home theater for a movie night. Rainy days will never be an issue here! Start or end your day on the lakeside deck breathing in the fresh air as you enjoy your morning coffee or an evening drink. On sunny summer days, hop in the boat to explore the lake or just relax on the private dock and go for a swim. Located on Lake Shore Drive, you are just minutes from all the action that the area has to offer. Fantastic restaurants, stylish boutiques, and an abundance of activities are just a short drive from the home! When you are ready to wind down after a day on the lake or on the slopes, you can come together in the great room to cozy up in front of the fire, or retreat to one of the 5 bedrooms for some quiet alone time. Whether you’re coming for a family getaway or a weekend away with your friends, a relaxing retreat or adventure-packed stay, The Bear Necessities has you covered! Book your stay today!brbrACCESS DETAILS:brLake Access and dock slip are located down from the back of the home. Please note that docks are only guaranteed from Memorial Day through Labor Day.brbrCOMMUNITY/AREA DETAILS:brThis home is located along Lake Shore Drive at Deep Creek Lake.brbrLAYOUT DETAILS:brMain Level: br- Kitchen br- Great Room br- Dining Room br- Powder Room br- LaundrybrbrLower Level 1: br- Study br- Indoor Poolbr- Bedroom (Suite): King Bed, Balcony/Deck,Attached Bath with Shower and Separate Tub br- Bedroom (Suite): Duo Bunk Bed, Attached Bath with Shower and Separate Tub br- Bedroom (Suite): King Bed, Attached Bath with Shower and Separate TubbrbrLower Level 2: br- Den/Game Area br- Powder Room br- Bedroom (Suite): King Bed, Attached Bath with Shower and Separate Tub br- Bedroom (Suite): Duo Bunk Bed, Attached Bath with Shower/Tub br- 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 5

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Bath 6

Bath

Sleep 14

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$1070.39

/ Nightly
Private Vacation Home

Bear on the Lake | Boat Dock, Hot Tub, Fire Pit

Oakland, Maryland, United States

Bear on the Lake is a brand-new vacation home on the shores of Deep Creek Lake, designed for comfort, relaxation, and unforgettable moments. This stunning three-story retreat features five bedrooms and four and a half bathrooms, offering plenty of space for families and friends. With three king-size suites, each with a private ensuite bathroom, everyone enjoys their own haven of comfort and privacy.brbrThe main level brings everyone together with its open floor plan, where a modern kitchen, inviting dining area, and cozy living room create the perfect gathering space. The kitchen features an espresso/cappuccino maker, two dishwashers for added convenience, and floor-to-ceiling windows frame lake views, filling the home with natural light and connecting you to the beauty outside. Step onto the deck to take in the scenery while sipping a freshly-made cappuccino, share a meal, or simply breathe in the fresh mountain air. The lower level family room features a game area with a pool table with a ping-pong top and convenient kitchenette with a second refrigerator! Upstairs, the loft offers panoramic treetop views — a serene spot to read, relax, or take in the scenery.brbrOutdoors, Bear on the Lake's private hot tub, lakefront fire pit, and furnished spaces make it easy to relax day or night. A private dock gives you direct access to the water, perfect for swimming, fishing, or heading out on the lake by boat. You’ll also find an indoor dog wash for your four-legged friends and an outdoor shower, ideal for rinsing off after lake time or a day of adventure.brbrLocated in the heart of Deep Creek Lake, you’ll be just minutes from favorite activities year-round, from hiking and golf to skiing at Wisp Resort. Several local favorite bars and restaurants are within walking distance - Uno's, Honi Honi, Acers Run, and Firewater. After a day of adventure, Bear on the Lake is your place to unwind, reconnect, and make lasting memories.brbrBe among the first to experience this brand-new lakefront getaway—book your stay today at Bear on the Lake and start planning the ultimate Deep Creek escape.
Bed 5

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Bath 5

Bath

Sleep 14

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$519.98

/ Nightly
Private Vacation Home

The Whiskey Barrel Lodge | Hot Tub & Firepit!

Oakland, Maryland, United States

Close to Deep Creek Lake and within walking distance of Honi Honi Bar and other area attractions, The Whiskey Barrel Lodge puts you at the center of everything. Surrounded by trees and mountains, this private vacation home replete with rustic charm has room for your whole group in an unbeatable location. The surrounding area is loaded with opportunities for nature lovers, from skiing at nearby Wisp Resort to golfing at Lodestone Golf Course to hiking in Deep Creek Lake State Park. Close to historic downtown Oakland with its many shops, museums, restaurants, festivals and more, The Whiskey Barrel Lodge offers both relaxation and endless options for entertainment all year round.brbrWith five bedrooms and two full bathrooms, The Whiskey Barrel Lodge is just right for extended family get-togethers or gatherings of good friends. The main level features the original hardwood flooring throughout, four comfortable, beautifully made up bedrooms (one with a queen-size bed, two with sprawling king-size beds, and kid’s bedroom with two twin-size bunk beds), a full bathroom with shower/tub combo and kitchenette complete with wet bar. The living room and bedrooms all have their own smart TVs so everyone can watch what they like. The ground floor offers extra privacy for families traveling together thanks to a second living room with smart TV, fifth bedroom with queen-size bed and smart TV, full bathroom with shower/tub combo and full kitchen with stainless steel appliances and everything you need to prepare and serve anything from a quick breakfast to a lavish meal on nights you want to eat in. An attached sunroom is a great spot to relax and enjoy listening to the songbirds, or you can step out onto the patio and fire up the gas grill for an old-fashioned family barbecue.brbrThe Whiskey Barrel Lodge’s many amenities include a bubbling hot tub perfect for soothing away real-world cares, free Wi-Fi to keep you connected and AC so you’re always comfortable. All towels and linens are provided, and a washer and dryer ensure you can refresh your wardrobe in a hurry.brbrCombining comfort and convenience in a fabulous location, The Whiskey Barrel Lodge will ensure your group makes memories that will last a lifetime. Book your Deep Creek Lake vacation today!
Bed 5

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Bath 2

Bath

Sleep 12

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$536.91

/ Nightly
Private Vacation Home

Endless Lake Views | Hot Tub + Game Room

Oakland, Maryland, United States

Endless Views- 4 BR Home w/ Hot Tub, Pool Table, Fireplace & Deck at Deep Creek LakebrbrEndless Views lives up to its name, offering breathtaking panoramic views of Deep Creek Lake. This spacious 4-bedroom, 4-bath home comfortably sleeps up to 10 guests and is perfect for families or groups looking for a relaxing lake getaway. Step into the main living area and be greeted by stunning floor-to-ceiling windows framing the lake and a cozy fireplace. The updated kitchen opens to the dining area, making it easy for everyone to enjoy meals together.brbrOutside, the expansive deck is the star of the show—take in the endless views of Deep Creek Lake while enjoying outdoor dining or grilling out. The lower level offers a second living area with another fireplace, along with a pool table and foosball for hours of entertainment. You'll also find a washer and dryer for your convenience. To complete your mountain-lake retreat, unwind in the private outdoor hot tub after a day on the lake or exploring the area. With incredible views, multiple gathering spaces, and great amenities, Endless Views is the perfect place to make unforgettable Deep Creek Lake memories.brbrIMPORTANT TO KNOW:br*This home's kitchen is equipped with a standard and k-cup style coffee pot.br*Max parking spaces for this home is 4; garage access is not availablebr*This home does not have cable tv (streaming is available using your own account)br*This home has exterior camera(s)br*This is a non-smoking/vaping propertybr*Check-in is between 4 pm- 9 pm; Check-out is by 10 am.br*Minimum age to rent is 25.brbrWHAT TO BRING:brPlease plan to bring your own supplies. One bath towel and one washcloth per person will be provided. Homes are equipped with cookware, dishes, drinkware, utensils, and bed linens for the max occupancy of the home. Propane will be provided for all propane grills; any refill requests can be made during normal business hours. Some items NOT provided include: paper products, food/spices, coffee filters, trash bags, detergents, soaps, toiletries, beach towels, firewood and makeup remover wipes (recommended to avoid fees for towel damage). brbrPETS:brThis home is not pet-friendly. Undisclosed pets will be charged a fee equal to 3x the standard pet fee, per pet. brbrWINTER RESERVATIONS:brA 4WD vehicle is required to access rentals between November through April. Private driveways will not be snow-plowed unless and until there is 5 inches of snow.brbrRESERVATION PROCESS: brWITHIN 24 HRS OF BOOKING, sign the Rental Agreement to begin receiving your pre-arrival information. (Door Codes will NOT be released without an e-signed agreement.) Once completed, your check-in instructions and door code will be automatically sent ONE DAY PRIOR TO ARRIVAL. If you do not receive this info, please check your spam folder first. If it is still missing, contact us before 4 pm to ensure a smooth check-in. *A non-refundable processing fee applies to all reservations.*brbr brBook your stay today and start making unforgettable memories in the beautiful Deep Creek Lake area!
Bed 4

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Bath 4

Bath

Sleep 10

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Exceptional(118)

$510.13

/ Nightly
Private Vacation Home

Peaceful Lakefront! Private deep water dock, evening sun, quiet dead end street!

Oakland, Maryland, United States

Welcome to a truly special lakefront experience on the shores of Deep Creek Lake. Located in a private community on a peninsula at the Northern end of the lake, our home offers peaceful relaxation far away from busy roads and traffic. Families with children or pets will especially appreciate the one lane road cul de sac location with no through traffic. brbrThe property features almost 100 feet of western exposure lakefront in a quiet cove with a large private dock. The dock is ideal for relaxing on sunny days, fishing, or swimming. Please note that the dock is only available from Memorial Day through the end of September. Sunsets are spectacular with sunshine lasting into the late summer evening hours. After sunset, you'll enjoy using the fire pit near the lakes edge. brbrThe house itself features a beautifully renovated kitchen and dining area with stainless steel appliances and maple cabinets. The house features a master bedroom with full bath, and two other bedrooms and a renovated hall bath, with beautiful ceramic tiles, new cabinetry and a jetted tub. The living room will evoke memories of classic lake lodges with its cathedral ceilings and stone fireplace and wonderful views of the secluded lakefront. brbrFor the ultimate in relaxation, there is an outdoor hot tub with a wonderful view of the lake. brbrThe house features a nice game room featuring a pool table, Smart TV and reclining sofa and chair. Across the front of the house is a large deck where you will enjoy barbecuing on the gas grill, dining outdoors on the patio furniture, or relaxing on the swing, all with a beautiful view of the lakefront and yard. brbrThe house sleeps 8 people, offering 3 queen size beds, and a queen size futon. We accept credit cards and require one half of the rent in advance to confirm the booking. Access to nearby restaurants, arcades, state parks, skiing, and whitewater rafting are a close drive away. brbrPlease note that from mid June through the end of August rentals are on a weekly basis. Check in is on Saturday and Check out the following Saturday.brbrPartial week rentals are available at all other times of the year.brbrKeywords: House
Bed 4

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Bath 2

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Sleep 8

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Exceptional(134)

$626.71

/ Nightly
Private Vacation Home

5 STAR OWNER Managed, Lake Xcess, dock, Pool, Pickle-ball, Home Theater, firepit

Oakland, Maryland, United States

****4 KING BEDS!!!!**** brbrCHECK OUR REVIEWS - PRIVATE OWNER MANAGED FOR 9+ YEARS! Lure of the Lake is a spacious (4000+ SQUARE FEET) and peaceful five bedroom, four bath, three level, air-conditioned home. Featuring a wall of windows and cathedral ceilings in the great room, as well as a cozy sun porch. This unique chalet brings the outdoors in with outstanding results. brbrThe spacious layout, casual décor and 2 master suites ensures comfort and ease for a gathering of family or friends, and puts your soul at ease and provides peace and quiet for your vacation. No matter what the weather, the covered porch invites you to sit back, relax and enjoy your view of the surrounding woodlands. The great room includes a 4K HD big screen TV with Blue-Ray player and gas fireplace - no need to carry wood! A cozy sectional relaxes you with electric recliners so comfortable you will fall asleep in them! Enjoy the fully equipped, gourmet kitchen, including all new appliances, that is perfect for family gatherings, that includes both a Keurig and regular coffee pot. The large dining room table seats up to 12 with counter stools to seat an additional three guests. While your family is enjoying a meal together, your view through the sun-room is of the surrounding woodlands full of wildlife. brbrThe private upper level MBR suite includes a king bed, private balcony, flat screen TV, and large bathroom including a two person Jacuzzi tub and separate shower. The second MBR suite is located on the main level with a king bed and private bath and is separated from other bedrooms (perfect for the in-laws!). A third bedroom on the main level also has a king bed and is adjacent to the main bathroom. The fourth bedroom also features a king bed and is adjacent to a full bath and bunk room, all on the lower level. The bunk room has two sets of bunk beds, one twin over twin and the other twin over full. This level also features a spectacular game room/home theater, including an Ohlhausen pool table, Pub/game table, Foosball table, bar, and 1080p HD home theater with a 100 screen, Blue-ray player and surround sound system.brbrIn addition to the home theater, 4 bedrooms include flat screen TV's with DVD players. The home is equipped with high speed wireless internet so that you can keep in touch or stream your favorite show, and there is a private work area upstairs for those people that must bring their work with them. Soak your worries away in the 7 person hot tub that is professionally cleaned after every guest stay. Warm your feet or even make s'mores by the outdoor firepit. Let the grill masters cook everyone dinner on the Weber gas grill. Full size washer, dryer, extra mini fridge, iron and ironing board in laundry room.brbrLocated in the Blakeslee community, a prestigious community because of its quiet, serene setting, and the numerous amenities available. The large, wooded lots provide a feeling of privacy and plenty of play area for the family. Walk or bike to the dock in a few minutes (the home is closer to the lake than what VRBO says!!!)...boat rentals are available at Bill's Marina. The community is fairly level and arranged in a circular (1.6 miles) fashion which makes it perfect for biking, jogging or just an afternoon stroll. In addition, there are 5 miles of hiking trails within the community, as well as trails for snowmobiles and ATV's. Deer, wild turkeys and other wildlife are often seen in the fields by the entrance to the community. The indoor 25' x 50' pool is located in the Community Center (closed on Tuesdays and Wednesdays and open Thursdays and Fridays from Noon to 8PM, and Saturdays, Sundays and Mondays from 10AM - 6PM) and includes a large club room with TV, comfortable chairs, tables and chairs and pool table. Two tennis courts and two pickle-ball courts, basketball court, soccer field and outdoor playground are all adjacent to the community center. The Community Center is literally across the street from the end of our driveway!!!brbrYou can visit many state parks close to our home. You can hike through Swallow Falls, swim at Muddy Creek Falls, use the boat ramp at the Deep Creek State Park, or enjoy the sand beach at the park. brbrAll of Wisp Mountain's skiing, snowboarding, snow tubing, mountain coaster, Segway tours, whitewater rafting and many other activities are within 15 minutes.brMovie theater, restaurants, golf, horseback riding and shopping are all within 5-10 minutes. The famous Honi Honi bar is only 5 miles away. And Deep Creek’s oldest pub, Pawn Run, with craft cocktails and signature small plates is a 5 minute drive.brbrOakland - There is a nice blend of retail businesses and services including antiques, high quality men and women’s clothing, locally owned full service pharmacies and even an old-fashioned soda fountain. There you can order a milk shake made the old fashioned way!br Oakland, Maryland is also the home to a restored 1884 train station, the new Transportation Museum and the County’s Historical Society Museum.
Bed 5

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Bath 4

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Sleep 12

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$436.32

/ Nightly
Private Vacation Home

A Cozy Hot Tub Hideaway w/ Fire Pit & Games

Oakland, Maryland, United States

Name: Dancing Bear Retreat | Bedrooms: 4 | Bathrooms: 3 | Sleeps: 11 | Access: Lake Area | Pets Not Permitted | MUST BE 24+ YEARS TO RENT | Free WIFI ProvidedbrbrDESCRIPTION:brIf you’re searching for the classic Deep Creek Lake log cabin, Dancing Bears Retreat is your perfect match. Nestled in a tranquil wooded community, this charming cabin offers the ideal blend of seclusion and convenience, just minutes from lake activities, skiing, and the natural beauty of the whole area. The open-concept main level is a showstopper, featuring large windows that invite the beauty of the outdoors inside. Gather in the great room by the cozy stone fireplace for a cozy movie night or to simply kick back and relax. The lower level family room is a haven for fun, packed with entertainment options to keep everyone engaged. Enjoy TV time, a game of shuffleboard, or a round of pool. Just outside, the bubbling hot tub invites you to soak and unwind in the crisp mountain air. The partially covered deck offers a serene spot to relax and take in the sounds of nature no matter the weather. As night falls, gather around the fire pit for s'mores and stargazing. Conveniently located to offer peace and privacy but never far from all the action, a short drive brings you to all of Deep Creek’s must-do activities, including the four-season Wisp Resort. Dancing Bears Retreat is the perfect destination for your next Deep Creek Lake getaway. Book your stay today!brbrACCESS DETAILS:brNo Additional Details Provided for this Home. brbrCOMMUNITY/AREA DETAILS:brLocated in the Deerfield Community at Deep Creek Lake.brbrLAYOUT DETAILS:brMain Level:br- Kitchenbr- Living Roombr- Dining Roombr- Bedroom: Queen Bedbr- Full Bath with Shower/Tubbr- Bedroom: Queen BedbrbrUpper Level:br- Loftbr- Bedroom (Suite): King Bed, Attached Bath with Shower/TubbrbrLower Level:br- Den/Game Areabr- Bedroom (Suite): Twin Bunk Bed, Duo Bunk Bed, Attached Bath with Showerbr- 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 4

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Bath 3

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Sleep 11

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Exceptional(5)

$1285.71

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Private Vacation Home

Dog Friendly, Private Dock, Fire Pit & Cozy Interiors

Oakland, Maryland, United States

Name: Paradise at Deep Creek | Bedrooms: 7 | Bathrooms: 5.5 | Sleeps: 18 | Access: Lake Front | Dogs Welcome (Max. 2) | MUST BE 24+ YEARS TO RENT | Free WIFI ProvidedbrbrDESCRIPTION:brWhat’s better than Paradise This dreamy lake-front home is the nature lover’s haven, with beautiful wooded areas, a private dock, and endless spots for sunbathing just steps from your door. Spend sunrise to sunset swimming and boating on the lake with no commute time, or pass the morning marveling at Deep Creek’s stunning nature from the raised deck, coffee in hand. Bring along your resident grillmaster to show off their skills and enjoy their delicious creations at the outdoor dining areas. Then, gather around the fire pit or take a dip in the hot tub while the calming sounds of the lake move around you. Once inside, the relaxation only continues - 2 fireplaces, an oversized jetted bathtub, and 6 TVs make for incredibly cozy evenings, and the pool table is just the cherry on top! Truly an escape, Paradise at Deep Creek has everything your group needs for the perfect vacation, whether you are planning to enjoy summer on the water, celebrate the holidays, or escape for the weekend. Book your stay in Paradise today!brbrACCESS DETAILS:brThis property comes with private lake access and a private dock slip located on the property. Please note that docks are only guaranteed from Memorial Day through Labor Day.brbrCOMMUNITY/AREA DETAILSbrLocated in the Paradise Point Community at Deep Creek Lake.brbrLAYOUT DETAILS:brMain Level:br- Great Roombr- Kitchenbr- Dining Roombr- Sunroombr- Bedroom (Suite): King Bed, Attached Full Bath with Showerbr- Powder Roombr- Laundry AreabrbrUpper Level:br- Loft Areabr- Bedroom (Suite): King Bed, Attached Full Bath with Showerbr- Bedroom: Queen Bedbr- Full Bath with Shower/Tubbr- Bedroom: King BedbrbrLower Level:br- Den/Game Area: Queen Sleeper Sofabr- Bedroom (Suite): King Bed, Attached full Bath with Shower and Separate Tubbr- Bedroom: Duo Bunk and Twin Bunk, Access to Shared Bathbr- Bedroom: Queen Bedbr- Full Bath with Shower/TubbrbrDISCLAIMERS: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.brbrDOG BREED LIMITATIONS: Even in dog-friendly homes, it’s prohibited to bring any dog with a history or instance of aggressive or reactive tendencies. We welcome any dog which you know to be well-socialized, trained, and friendly in any situation involving others, both human and canine, as there may be nearby dogs at neighboring properties. However, due to restrictions in place by homeowner insurance policies, breeds listed as most aggressive are banned from all rentals, regardless of the training and temperament of the individual dog. For a list of restricted breeds and our full policy regarding dogs, please contact us directly.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 7

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Bath 5

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Sleep 18

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Exceptional(14)

$466.32

/ Nightly
Private Vacation Home

Iconic Cabin! Hot tub, fire pit, lakefront, dock, pet friendly and more!

Oakland, Maryland, United States

Lake Haven just listed with Red Barn Vacations. The home was previously five star-rated. 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!brbrLake Haven is the perfect home for your lake getaway! With 100ft of amazing, level lake front that is exclusively yours to enjoy; you can hop into your boat from the private dock in seconds to explore the lake, or sit inside and take in the expansive lake views from any room. While the boat photographed in the gallery is not available for renter use, the home does comes with a canoe and a kayak for your use! (The boat will be moored in the dock slip, but renters do have use of the dock and may dock a boat to the side of the dock)brbrLocated in a quiet cove that is a fishing enthusiast's delight, you can take in the sunrise views and get some fishing done, or take a leisurely swim around the cove anytime you please. It has two tables for outdoor dining, and a grassy lawn that has plenty of room for the kids to run and play. At the end of the day, you can wind down around the glow of the fire pit by the lakeshore or relax in the hot-tub with a view of the lake and the starry mountain skies above you. brbrThe interior is bright and airy, and decorated in a charming cottage style that is immediately inviting. The single-level floor plan is ideal for sharing quality time with your favorite people. Gather together in the great room to enjoy lake views from the comfort of the sectional sofa or cook up a storm in the adjacent, eat-in kitchen that features a farmhouse sink, ample counter space and all the essentials for making delicious meals. You can also cook on the grill outdoors, and eat at the picnic table as you watch boats cruising by.brbrAdding to your living space is a family room where you can watch TV on the wall-mounted flat screen TV while the kids play foosball. A pass through window to the kitchen makes it easy to serve drinks and snacks for a relaxed evening at home.brbrAll bedrooms have views of the lake, and attention to detail guarantees a good night's sleep in each of the rooms. The spacious primary suite with a queen bed has its own entrance so that guests can come and go as they please. Grab a book off the shelf and settle in to one of the rocking chairs to lose yourself in a story. A second bedroom with two bunk beds is the perfect spot for the kids, and they will love having their own space! The third bedroom is furnished with a queen bed and a reading nook by the window to take in the lake views.brbrWhen you stay at Lake Haven, you are off-the-beaten path yet about ten minutes from favorite restaurants like Dutch's at Silver Tree and Uno Pizzeria & Grill. You can also easily reach marinas, shops, mini golf, and more. Circle R Ranch down the road offers horseback Trail Rides and Horse Drawn Sleigh Rides through old apple orchards and the beautiful countryside. br​​​​​​​brYear-round fun at Wisp Resort is just twenty-minutes away. Wisp is well-known for skiing, golf, snow tubing, zip lines, and more. Plus, they operate the world's only mountaintop white water rafting course. brIf you enjoy hiking or mountain biking, you will be minutes away from Deep Creek Lake State Park and Swallow Falls, where you can enjoy breathtaking waterfalls and scenic trails. Ohiopyle State Park is a short drive away, with some of the best whitewater rafting in the eastern U.S.! Also near Ohiopyle you will find two homes designed by renowned architect, Frank Lloyd Wright - Fallingwater and Kentuck Knob. brFrom the beautiful décor, to the lake steps away, and a choice of activities to enjoy all around, Lake Haven will make your vacation a true pleasure!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. * 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 3

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Bath 2

Bath

Sleep 8

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