Home Vacation Home Rentals By Owner In Oakland, MD

Showing 220 Of 363 Vacation Rentals
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Exceptional(13)

$685.14

/ Nightly
Private Vacation Home

Ferndale: New, Lake Access w. Dock Slip, Hot Tub, Dogs OK

Oakland, Maryland, United States

3 Bedrooms, 3.5 Baths, Sleeps 7, Dog Friendly with additional $100 fee/pet paid after booking brBed sizes: King, King, King and Daybed with Trundle brbrFerndale is designed to deliver the best experience for your family and friends. It offers three suites, indoor and outdoor living space, a private hot tub, and nearby lake access with a boat slip. Plus, it is dog friendly! Skiing and golf at Wisp Resort, Swallow Falls State Park, popular restaurants, and favorite activities are nearby. brbrTIMBER ROCK VILLAGE RESORT AMENITIES INCLUDED WITH YOUR STAYbrAs a Timber Rock Village guest, Ferndale comes with access to resort-level community amenities that no other Deep Creek Lake rental can match:brbr-The Reserve: 70'x20' saltwater pool with waterslide, large hot tub, covered pavilion with fireplace, showers, and ADA lift. Open Memorial Day through mid-October (weather permitting).br-Fitness facility: 24-hour gym with Life Fitness equipment, two treadmills, stationary bike, cable machine, free weights, and a massage room.br-On-site massage/wellness services through Mother Maiden Crone Bodywork Shop.br-The Lodge: on-site concierge, multiple fire pits (Solo wood-burning and gas), and seasonal events including wine tastings and children's activities.br-Complimentary kayaks, paddleboards, and an inflatable Reef lounge (reservations required, limited availability).br-Bocce ball, cornhole, and giant Jenga available for pickup at The Lodge.br brSPACIOUS INTERIOR brEach home in Timber Rock Village is thoughtfully designed and outfitted with all of the essentials for a truly carefree vacation. Ferndale promises to be a place where you will want to return year after year. brbrThe open concept main level features a great room with ample seating surrounding the cozy glow of the electric fireplace. It is a place where you will feel right at home as you unwind while streaming your favorite show. brbrSharing meals together is one of the best ways to make memories when traveling with family and friends. With seating at the dining table and kitchen island, it is easy to gather for good food and lively conversation. The kitchen is equipped with all the essentials and extras that make meal prep a breeze. You also have easy access to the deck and gas grill for summertime cookouts. br brEveryone will appreciate the privacy and comfort of the three en suites. One is on the main level and the others are upstairs. Two of them feature a king-sized bed, and a 42” TV (streaming). The third has a king-sized bed, 42 TV, and a daybed with a trundle. br brOUTDOOR LIVING SPACE brTucked among the trees, Ferndale has two covered porches where you can savor the sounds of nature no matter what the weather. Evenings are best spent toasting marshmallows at your fire pit under starry mountain skies. Take a soothing soak in your private outdoor hot tub after a day spent skiing, hiking, or biking – total relaxation awaits! br brCOMMUNITY LAKE ACCESS brA short walk leads you to the path for the community lake access. Fill sunny summer days with swimming, fishing, and kayaking. At the end of the day, you will be treated to a breathtaking sunset. br brBring your boat or rent one locally to take advantage of your assigned dock slip. It is the ultimate convenience allowing you to take a cruise any time you please. br brAREA ATTRACTIONS brExperiencing the best of Deep Creek Lake is a breeze with four seasons of fun at your fingertips. Wisp Resort's year-round adventures are within a ten-minute drive. Skiing, snow tubing, white water rafting, ziplines, and golf will keep everyone entertained. Popular restaurants, shops, and mini golf are also nearby. brbrSwallow Falls State Park is a must for any Deep Creek Lake vacation, and it is only four miles from Ferndale. Explore miles of trails that lead to three stunning waterfalls. This is a great spot to visit with your pet between Labor Day and Memorial Day when leashed dogs are allowed in the park. brbrSmall town charm can be found in abundance when you visit Oakland's historic downtown. The streets are lined with unique eateries, antique shops, museums, and stores featuring the work of local artists. brbrReserve today and make Ferndale your destination at Deep Creek Lake! brbrPlease note, there is an exterior security camera in the driveway.
Bed 3

Bed

Bath 3

Bath

Sleep 7

Sleeps

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Exceptional(5)

$533.94

/ Nightly
Private Vacation Home

Woodsy Retreat w/ Fire Pit, Hot Tub & Game Room

Oakland, Maryland, United States

Name: Happy Hoursss... Hideaway | Bedrooms: 5 | Bathrooms: 6 | Sleeps: 14 | Access: Lake Area | Pets Not Permitted | MUST BE 24+ YEARS TO RENT | Free WIFI ProvidedbrbrDESCRIPTION:brReady to relax Nestled in the Deep Creek woods, Happy Hoursss…Hideaway is the serene spot you’ve been looking for, and its many thoughtful amenities are just the cherry on top! Whether you’re planning a summer getaway or a winter retreat, this home is sure to please your family and friends. Grill up your favorites and enjoy delicious meals together at the family-style dining table or have your breakfast sunnyside-up at one of the outdoor tables. Lounge the days away in the outdoor swinging chairs, just a few steps from the fire pit to ensure you are still able to grab a s’more! With lawn games and a game room including a pool table, a classic arcade cabinet, and a shuffleboard table, a bit of friendly competition is inevitable. Once the score is settled, finish your day stargazing in the hot tub or curled up in front of the fireplace with your favorite movies. Then, enjoy sweet dreams of another fantastic day at Happy Hoursss...Hideaway. Your new home-away-from-home is waiting for you - book your stay today!brbrACCESS DETAILS:brNo additional details provided for this home.brbrCOMMUNITY/AREA DETAILS:brLocated in The View Community at Deep Creek Lake.brbrLAYOUT DETAILS:brMain Level:br- Kitchenbr- Great Roombr- Dining Areabr- Full Bath with Shower/Tubbr- Bedroom (Suite): King Bed, Attached Bath with Shower/Tubbr- Mud Room/EntrybrbrUpper Level: br- Bedroom (Suite): Queen Bed, Attached Bath with Shower and Separate TubbrbrLower Level:br- Den/Game Area with Wet Barbr- Full Bath with Shower/Tubbr- Bedroom: Queen Bed, Twin Bunk Bed, Access to Shared Bathbr- Bedroom (Suite): Queen Bed, Full Sleeper Sofa, Attached Bath with Shower/Tubbr- Bedroom (Suite): Queen Bed, Queen Sleeper Sofa, Attached Bath with Shower/Tubbr​​​​​​​- 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

Bed

Bath 6

Bath

Sleep 14

Sleeps

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Exceptional(1)

$279.65

/ Nightly
Private Vacation Home

Lakeview Retreat | Lakefront w. Amazing Views, Boat Slip

Oakland, Maryland, United States

Welcome to Lakeview Retreat, a lakefront townhome on Deep Creek Lake offering unobstructed water views and a peaceful setting for your next getaway. This unique split-level, three-bedroom, two-bathroom retreat comfortably accommodates up to eight guests and is designed to showcase the beauty of the lake from every level.brbrThe main living area features a spacious layout with a large sectional sofa, Smart TV, and a cozy wood-burning fireplace—perfect for relaxing after a day on the water. Step out onto the lakefront balcony to take in breathtaking sunrises over Deep Creek Lake and unwind with vibrant sunset views in the evening.brbrJust a few steps down, you’ll find the dining area with seating for eight and an open galley kitchen with stainless steel appliances, making it easy to gather and enjoy meals together. The thoughtful multi-level design continues upstairs to a loft-style living area with a sleeper sofa and Smart TV, offering additional space to relax or accommodate extra guests. This level also features a queen bedroom with a workspace desk and a full bathroom.brbrOn the lower level, two additional bedrooms provide comfort and convenience. The king bedroom includes a Smart TV, in-home stacked washer and dryer, and direct access to a lakefront patio—perfect for stepping outside and enjoying the view. The second bedroom offers a queen bed and a private exterior entrance, along with a full bathroom on this level.brbrGuests of Lakeview Retreat enjoy community lake access with a private boat slip, making it easy to spend your days boating, fishing, kayaking, or paddleboarding. Additional community amenities include a fire pit, basketball court, and tennis courts for even more ways to enjoy your time outdoors.brbrLocated in the heart of Deep Creek Lake, you’re just minutes from local dining, shops, and year-round activities—from hiking and golf to skiing at nearby Wisp Resort. Whether you’re seeking adventure or a quiet escape by the water, Lakeview Retreat offers the perfect balance of comfort, convenience, and stunning lakefront scenery.brbrBook your stay today and start making memories at Deep Creek Lake.
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

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Exceptional(6)

$1942.3

/ Nightly
Private Vacation Home

Grand Chestnut Lodge | Lakefront w/ Game Room, Hot Tub & Dock!

Oakland, Maryland, United States

Retreat to the newly renovated Grand Chestnut Lodge (formerly Sunset Delight), where rustic lakefront charm and contemporary luxury come together. This gorgeous, lakefront home offers the ideal space for friend and family reunions, as well as corporate, church, and yoga retreats.brbrGrand Chestnut Lodge boasts five elegantly appointed suites on the main and upper levels, each with its own large, private full bath. Additionally, there are four bedrooms connected by Jack and Jill baths on the lower level. Most of the bedrooms boast king-size beds and are outfitted with additional beds allowing for maximum flexibility for families. Enjoy new bedding, decor, and televisions in each room. The romantic suite on the main floor also has a gas fireplace in the bedroom.brbrA new, gourmet chef's kitchen complete with an extraordinary 20-foot-long island keeps your whole group together right where they want to be! The kitchen is fully equipped with two double-door refrigerators, two dishwashers, a bar, an ice maker, and a double-stack oven. Meals can be enjoyed indoors on the massive island, at the great room dining table with a crackling fire in the background or taken outdoors on the spacious deck.brbrA wealth of amenities awaits, including a private Type A dock, extra-large hot tub, pool table, arcade games, and a 20-person fire pit.brbrStep into Grand Chestnut Lodge’s design-forward interiors, highlighted by a towering stone fireplace, two-story windows, and upscale décor. The oak-dappled lawn offers ample space to play and leads to your private dock. The large lawn is ideal for family activities, peaceful yoga sessions, or simply basking in the sun. A lakefront swing allows you to enjoy sunsets over the lake. The lakefront firepit is outfitted with plenty of Adirondack chairs and chaise lounge chairs for everyone.brbrThis location simply can’t be beat! Offering privacy on its massive lakefront lot, the property is conveniently located on a short paddle, boat ride, or drive from local attractions. Kayak a few docks over to enjoy dining and a playground for the kids. A five-minute drive in either direction will take you to restaurants, shops, a movie theater, and Deep Creek Lake State Park. Drive just a few minutes further to ski, golf, snow tube, mountain bike, and more at Wisp Resort. Enjoy hiking trails in the state park one mile from the house or pick from six other state parks to explore. Each park offers a portfolio of hiking trails, sandy beaches for swimming, stunning waterfalls, and abundant wildlife.brbrPet-friendly with space for two small dogs (under 25 lbs), Grand Chestnut Lodge invites you to reserve your stay now and experience the perfect synthesis of rustic charm and modern luxury. Don't miss the chance to immerse yourself in an extraordinary lakefront experience. Book now before your desired dates are taken!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 9

Bed

Bath 8

Bath

Sleep 24

Sleeps

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Exceptional(3)

$859.79

/ Nightly
Private Vacation Home

Cozy Lakefront Retreat w/Dock, Hot Tub & Fireplace

Oakland, Maryland, United States

Name: Lake Shore Landing | Bedrooms: 5 | Bathrooms: 4 | Sleeps: 12 | Access: Lake Front | Pets Not Permitted | MUST BE 24+ YEARS TO RENT | Free WIFI ProvidedbrbrDESCRIPTION:brTucked in the trees along Lake Shore Drive you will find this beautiful lakefront home. Enter the home to find stunning wood walls and ceilings highlighted by the panel of floor to ceiling windows over looking the lakefront. Enjoy the best of all seasons with ways to entertain no matter what the weather. In the summer and fall, gather on the upper section of the deck for dinner and grilling or on the lower section to catch some rays and relax. Follow the path down to the lake to enjoy fun on the lake or on the dock and come back to soak in the bubbles of the hot tub. On those rainy falls days or snowy winter ones, curl up on the sectional in the living room, throw on your favorite movie and feel the warmth of the fireplace as the snow cascades outside the windows or head downstairs and shoot a game on the pool table. Get out of the house to grab lunch or dinner at the local favorite restaurants before hitting up one of the arcades for games, laser tag, go-karts and more! Located near the heart of Deep Creek Lake, you will never run out of things to do all year round. Hurry and plan your next DCL vacay at Lake Shore Landing! We can’t wait to have you! brbrACCESS DETAILS:brLake Access and dock are located down the path from the back deck. 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.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 occupancy.brbrLAYOUT DETAILS:brMain Level:br- Kitchenbr- Dining Areabr- Living Areabr- Full Bath with Showerbr- Saunabr- Bedroom (Suite): King Bed, Attached Bath with Shower and Separate Tubbr- Laundry (located in Room off Garage)brbrUpper Level:br- Bedroom (Suite): King Bed, Attached Bath with Shower/Tubbr- Bedroom (Suite): 2 Full Beds with Twin Trundles, Attached Bath with Shower/Tubbr- Bedroom: Queen Bed br- Bedroom: Queen Bedbr- Full Bath with ShowerbrbrLower Level:br- Den/Game AreabrbrDISCLAIMERS: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

Bed

Bath 5

Bath

Sleep 12

Sleeps

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Exceptional(1)

$738.11

/ Nightly
Private Vacation Home

Secluded Lake Escape w/ Dock, Fire Pit & Views

Oakland, Maryland, United States

Name: Sylvan Sweet | Bedrooms: 5 | Bathrooms: 4.5 | Sleeps: 14 | Access: Lake Front | Pets Not Permitted | MUST BE 24+ YEARS TO RENT | Free WIFI ProvidedbrbrDESCRIPTION:brLooking for a serene vacation destination Then look no further as Sylvan Sweet is the home for you! Thoughtfully located along the lakefront, this well-appointed home sits nestled away amongst the trees providing you with unlimited privacy while still being right on the water. After a day of travelling arrive to your home away from home where you are welcomed by rustic décor with ample seating areas and large windows allowing in the warm sunlight. No matter the season there is plenty to do! On a cool fall evening make sure to enjoy the walking trail that runs along the lakefront or on warm summer days walk down to your designated dock slip and take a dip in the cool refreshing water. When you’re ready to go out to explore, you’re only a few miles from many activities including Fork Run Recreation Area, Swallow Falls State Park, and Wisp Resort — along with all the other shops, restaurants, and attractions on Garrett Highway. Come home for the evening and take advantage of the many amenities including a family game night on the pool table or ease those muscles in the warm bubbles of the hot tub. Finish off in front of the outdoor firepit roasting smores and sharing your favorite vacation memory! Book your stay 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 DETAILS:brLocated in the Stockslager Community at Deep Creek Lake.brbrLAYOUT DETAILS:brMain Level:br- Kitchenbr- Living Roombr- Dining Roombr- Powder Roombr- Sitting Areabr- Full Bath with Shower/Tubbr- Bedroom: 2 Full Bedsbr- Bedroom: Queen Bedbr- Bedroom (Suite): Queen Bed, Attached Bath with Shower/Tubbr- Bedroom (Suite): King Bed, Attached Bath with Shower/Tubbr- LaundrybrbrUpper Level:br- Loft Areabr- Bedroom (Suite): King Bed, Attached Bath with Shower/TubbrbrAbove Garage:br- Game AreabrbrDISCLAIMERS: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

Bed

Bath 4

Bath

Sleep 14

Sleeps

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Exceptional(1)

$523.61

/ Nightly
Private Vacation Home

Rustic Elegance w/ Hot Tub, Game Loft & Fireplace

Oakland, Maryland, United States

Name: Blended | Bedrooms: 4 | Bathrooms: 4 | Sleeps: 12 | Access: Lake Access | Pets Not Permitted | MUST BE 24+ YEARS TO RENT | Free WIFI ProvidedbrbrDESCRIPTION:brWelcome to Blended, your luxurious retreat nestled amidst the serene landscape of Deep Creek Lake. Located in the Blakeslee Community, this expansive vacation rental boasts spacious living areas adorned with modern furnishings and rustic accents, creating an atmosphere of cozy elegance. Gather with loved ones in the inviting living room, where a stone fireplace invites cozy evenings. The fully equipped kitchen and adjacent dining area provide the perfect setting for memorable meals together. Step outside onto the expansive deck and immerse yourself in the tranquility of your surroundings, whether soaking in the bubbling hot tub under the stars or grilling up a feast for al fresco dining. For recreation, indulge in the ultimate entertainment experience in the above garage game space, featuring a pinball machine, arcade games, and an air hockey table. Additionally, embark on outdoor adventures right from your doorstep, from boating and fishing on the lake to hiking and biking through the lush forests. In winter, hit the slopes at nearby Wisp Resort for exhilarating skiing and snowboarding. Enjoy the community amenities of an indoor pool, playground, tennis courts, and quiet roads perfect for a morning or evening stroll. After a day of exploration, retreat to the comfort of the home and indulge in relaxation with a rejuvenating soak in the hot tub or a soothing evening by the outdoor fire pit, sharing stories and s'mores beneath the night sky. With its idyllic setting and convenient access to both nature and local attractions, Blended offers the ultimate Deep Creek Lake experience for your unforgettable getaway. Book your stay today and discover the perfect blend of luxury, entertainment, and natural beauty at Blended.brbrACCESS DETAILS:brLake access can be found at three dock structures located throughout the community grounds. Please note that docks are only guaranteed from Memorial Day through Labor Day.brbrCOMMUNITY/AREA DETAILS:brThis home is located in the Blakeslee Community at Deep Creek Lake.brCommunity Indoor Swimming Pool: Open Thurs.- Fri. 12:00p.m. - 8:00p.m., Sat.- Mon. 10:00a.m. - 6:00p.m., Closed Tues. and Wed.brbrLAYOUT DETAILS:brMain Level:br- Kitchenbr- Living Room: Full Sleeper Sofabr- Dining Roombr- Bedroom: Queen Bedbr- Full Bath with Showerbr- Bedroom (Suite): King Bed, Daybed with Trundle, Attached Bath with Showerbr- Mud Room with LaundrybrbrLoft/Area Above Garagebr- Game/Den Areabr- Full Bath with ShowerbrbrUpper Level:br- Loft Spacebr- Full Bath with Shower/Tubbr- Bedroom: Queen Bedbr- Bedroom: Queen BedbrbrDISCLAIMERS: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

Bed

Bath 4

Bath

Sleep 12

Sleeps

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Exceptional(10)

$594.44

/ Nightly
Private Vacation Home

Elevated Dog Friendly Escape w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

Name: Morning Star | Bedrooms: 6 | Bathrooms: 5.5 | Sleeps: 16 | Access: Lake Area | Dogs Welcome Max. 2 | MUST BE 24+ YEARS TO RENT | Free WIFI ProvidedbrbrDESCRIPTION:brMorning Star is a beautiful home with an amazing level of quality! This mountain-top retreat was meticulously crafted with the vacation experience in mind, offering an unrivaled retreat at the lake. You’ll love how the modern design and spacious layout enhances the time spent together with family and friends! Whether you are simmering in the outdoor hot tub or enjoying morning coffee out on the deck, you are guaranteed days full of rest and relaxation. Love to golf Morning Star has you covered! Located near Wisp Resort’s Lodestone Golf Course, it's easy to get in a round or two during your vacation.brbrACCESS DETAILS:brLocated less than one mile from the entrance to Lodestone Golf Course. This golf course is one of the largest on the East Coast with sweeping lake and mountain views.brbrCOMMUNITY/AREA DETAILS:brLocated in the Greenbrier 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 occupancy.brbrLAYOUT DETAILS:brMain Level:br- Living Areabr- Dining Areabr- Kitchenbr- Bedroom (Suite): King Bed, Attached Bath with Showerbr- Half Bathbr- Laundry Areabr- Bedroom (Suite): King Bed, Attached Bath with ShowerbrbrUpper Level:br- Loftbr- Bedroom: King Bedbr- Bedroom: King Bedbr- Full Bath: Shower/Tubbr- Sitting Area: Queen Sleeper Sofabr​​​​​​​brLower Level:br- Den: Bar, Game Roombr- Bedroom (Suite): King Bed, Attached Bath with Shower/Tubbr- Bedroom: King Bedbr- Full Bath: 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.brbr​​​​​​​DOG 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. You can view this restriction list and our full policy regarding dogs at https://www.deepcreek.com/contact-railey under “Pet Policies”.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 6

Bed

Bath 5

Bath

Sleep 16

Sleeps

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Exceptional(23)

$458.98

/ Nightly
Private Vacation Home

Elegant Home Away: Hot Tub, Game Room, Kid Friendly!

Oakland, Maryland, United States

The perfect location for your Deep Creek escape! Enjoy a quiet retreat in this custom-built oasis near the golf course! Amenities galore: ping pong, foosball, arcade HeadsUp poker, hot tub, disc golf, basketball, golf driving net, kids’ tree fort and play room! Relax by the gas fireplace or in the hot tub after a day of hiking or skiing. Easy access to the fun of Deep Creek (10 min to Herrington/Broadford, 2 min to historic downtown, easy drive to DCL/Swallow Falls/WISP ski resort)! brbrThe spacebrYou’ll have full access to every part of this 4-acre property with a 3-hole disc golf course on site.brbrThe charm of this custom-built home shines from every carefully-planned area:brbr-Newel post at the bottom of the stairsbrcame from gazebo in downtown Oakland in the late 1800sbr- Arched front porch matches the interior arches in the kitchen and represents the flow of the Youghiogheny Riverbr- Stacked stone indoor gas fireplace carries same arch; represents the flowing riverbr-Cherry floors and cabinets made from the cherry trees on the property when cleared to buildbrbrWork from home as desired in your private office or escape from work playing ping pong, foosball, or darts in the game room.brbrGolf is across the street! Wisp Ski Area is a short drive, Swallow Falls and Herrington Manor are just two gorgeous State Parks within a few miles. Deep Creek Lake is less than 5 miles. Oakland is 2 minutes away to hit the farmer's market and great shopping or to savor the eclectic food and brewery options. This property is the perfect location for your Deep Creek vacation! Please reach out if you are interested in a chartered tour of the lake on a pontoon boat or wake surfing boat during your stay! (Upon request, subject to availability.)brbrOther things to notebr4x4 strongly recommended for winter stays. The driveway and surrounding areas are difficult to traverse in wintry weather.
Bed 4

Bed

Bath 3

Bath

Sleep 14

Sleeps

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Exceptional(2)

$388.39

/ Nightly
Private Vacation Home

Sidetracked | Luxe Details, Backyard Pavilion, Fire Pit + Convenient Location!

Oakland, Maryland, United States

Welcome to Sidetracked, located in the charming neighborhood of Mountainside, West Deep Creek Lake, Maryland. This incredible rental property offers a one-of-a-kind vacation experience surrounded by scenic serenity.brbrIn the heart of nature, Sidetracked brings together the comforts of a luxury vacation with the peace of a secluded getaway. The property features a covered backyard pavilion & fire pit, perfect for unwinding after a day of exciting nearby outdoor activities. The spacious balcony and patio provide ample room to indulge in picturesque wooded views.brbrThe home's interior offers a cozy refuge for your stay. With air conditioning, heating, fireplace, and smart TVs, you'll want for nothing during your stay. The precisely equipped kitchen, which includes a coffee maker, dishwasher, and an array of cookware, makes meal preparation a breeze.brbrOffering three bedrooms that comfortably sleep up to eight guests, each room beautifully captures the spirit of this stunning rental property. Linens are provided for every room and bath towels for each of the three sparkling bathrooms.brbrSituated conveniently near a variety of attractions, Sidetracked offers an array of experiences at your fingertips. Try your hand at fly fishing, explore state parks, get competitive on the golf course, or visit local museums. With so many options, your adventure is simply a few steps away.brbrTake time off the beaten path and give yourself the vacation you deserve. Book your stay at Sidetracked today to enjoy nature in comfort and style.brbr**Please Note: This property's gas fireplace is turned off for the summer season**brbr*Please Note: A 4WD vehicle is required in winter months (November - March).
Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps

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Exceptional(2)

$398.52

/ Nightly
Private Vacation Home

Private Dog Friendly Mountain Cabin w/ Hot Tub

Oakland, Maryland, United States

Name: Howie's Landing | Bedrooms: 3 | Bathrooms: 2 | Sleeps: 6 | Access: Lake Area | Dogs Welcome: Max 2 | MUST BE 24+ YEARS TO RENT | Free WIFI ProvidedbrbrDESCRIPTION: brYour mountain vacation awaits you, and your family here at Howie’s Landing! This home is the perfect location if you are looking for privacy and seclusion, yet it is still only a few miles away from all the fun activities here at Deep Creek. You also can bring along your furry friends! When you arrive, you are greeted by beautiful foliage surrounding the home. Walk in and be welcomed with a rustic, country décor with modern accents. Begin your morning out on the deck breathing in the mountain air or take a small walk down the road enjoying the nature all around. Kick off your vacation right no matter the season! In the Summer rent a boat and take the family tubing, and then take a break and dock at the array of family restaurants along the lake. Explore the nearby State parks, or head over to the Four Seasons Wisp Resort and ride the mountain coaster! Coming in the Winter season Pack your snow gear and spend the day on the slopes skiing, snowboarding or tubing. Take your family to the local movie theater or check out the Deep Creek Fun Zone for arcade games, laser tag, and more family fun. Then come home and start up the grill for a dinner on the picnic table. After that take time to unwind in the warm bubbles of the hot tub, then finish the evening out by the fire pit sharing your favorite vacation memory! It’s time to kick back and relax, book your stay today!brbrACCESS DETAILS: brNo additional details provided for this home. brbrCOMMUNITY/AREA DETAILS: brThis home is located along Lake Shore Drive at Deep Creek Lake.brbrLAYOUT DETAILS: brMain Level: br- Kitchenbr- Living Roombr- Dining Areabr- Full Bath with Shower/Tubbr- Bedroom: King Bedbr- Bedroom: Full BedbrbrUpper Level:br- Bedroom (Suite): King Bed, Balcony, Attached Bath with ShowerbrbrLower Level:br- Den Areabr- 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.brbrThere is a working wood fireplace available for use, however firewood is not provided. Locally available for purchase.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 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

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Exceptional(2)

$815.83

/ Nightly
Private Vacation Home

Charming Dog Friendly Cottage w/ Modern Touches

Oakland, Maryland, United States

Name: Middleton Cottage | Bedrooms: 4 | Bathrooms: 3 | Sleeps: 12 | Access: Lake Access | Dogs Welcome (Max. 2) | MUST BE 24+ YEARS TO RENT | Free WIFI ProvidedbrbrDESCRIPTION:brNestled in the highly sought-after Blakeslee Community, Middleton Cottage is truly a unique home. Enter the home to be amazed at the stylish modern interior that combines rustic elements with sleek aesthetics. Walk through the home and take in all the unique elements that the home has to offer like the swinging couches and beds, stunning stone fireplaces, and an oversized open concept main level. Outside the home, the details continue. With a large warping porch with couch swing perfect for your morning coffee, outdoor dining table, outdoor shower, and more this home has something for everyone to enjoy! In the evenings gather around the fire pit and share stories under the starry sky or enjoy a soak in the hot tub. If you can pull yourself away from this stylish home, venture out to explore the community amenities like the pool, playground, lake access, and quiet roads perfect for an evening stroll. Or go further to take in all that the lake area has offer like fantastic restaurants, cute shops, arcades, the four-season Wisp Resort and so much more! Return home at the end of a busy day and curl up on the couches in front of the immaculate stone fireplace for a relaxing evening or gather around the pool table for a game before retiring to the bedrooms for a peaceful and restful nights sleep. If you are looking for a peaceful retreat at the house or an adventure-packed stay, Middleton Cottage is ready to host you! Book now and create unforgettable memories in this stunning cottage!brbrACCESS DETAILS:brLake access can be found at three dock structures located throughout the community grounds. Dock Slip is located at Dock Area #2. Please note that docks are only guaranteed from Memorial Day through Labor Day.brbrCOMMUNITY/AREA DETAILS:brThis home is located in the Blakeslee Community at Deep Creek Lake.brCommunity Indoor Swimming Pool: Open Thurs.- Fri. 12:00p.m. - 8:00p.m., Sat.- Mon. 10:00a.m. - 6:00p.m., Closed Tues. and Wed.brbrLAYOUT DETAILS:brMain Level:br- Kitchenbr- Living/Game Roombr- Dining Roombr- Full Bath with Shower/Tubbr- Bedroom: King Bedbr- Sitting Roombr- Bedroom (Suite): King Bed, Attached Bath with Shower and Separate Tubbr- LaundrybrbrbrUpper Level:br- Bedroom: Queen Bed, 3 Twin Beds, Access to Shared Bathbr- Full Bath with Shower/Tubbr- Bedroom: King Bed, Twin Bunk BedbrbrDISCLAIMERS: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 4

Bed

Bath 3

Bath

Sleep 12

Sleeps

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Exceptional(8)

$574.76

/ Nightly
Private Vacation Home

Modern Dog Friendly Cabin w/ Pool & Hot Tub

Oakland, Maryland, United States

Name: Blue Skies | Bedrooms: 5 | Bathrooms: 4 | Sleeps: 14 | Access: Lake Area | Dogs Welcome (Max. 2) | MUST BE 24+ YEARS TO RENT | Free WIFI ProvidedbrbrDESCRIPTION:brLocated just minutes from all the action, Blue Skies offers convenience and comfort all in one place! Step inside and be greeted by a warm and inviting atmosphere. The open concept main level features rustic yet modern furnishings, creating a comfortable and cozy space to unwind after a day of exploration. Snuggle up by the crackling fireplace in the spacious, sunken living room, or gather around the dining table for a delicious home-cooked meal prepared in the fully equipped kitchen. The upper loft is great for an afternoon hangout and the lower level den and game area is perfect for evenings when you just want to stay home. The large bar is great for whipping up your favorite drinks while shooting a game of pool with your friends. The outdoor spaces are just as great as the interior. Sit on the covered front porch with your morning coffee breathing in the fresh air as you listen to the birds chirping. Or gather around the fire pit for storytelling as the fire crackles in front of you before heading up to the deck to enjoy a soak in the bubbling hot tub. When you are ready to get out and explore, this home is perfectly situated close to all the action while still allowing plenty of privacy. Head to the state park for a hike or a day at the beach, rent a boat for the day and see the lake by water before stopping at one of the lakefront restaurants for lunch or dinner. In the winter head to the northern tip of the lake to the Wisp Resort for tubing, skiing, or snowboarding. No matter the season, Blue Skies is here to make sure you vacation is one to remember! Book today!brbrACCESS DETAILS:brNo additional details provided for this home.brbrCOMMUNITY/AREA DETAILS:brLocated along Zeddock Miller Rd 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 occupancy. brbrLAYOUT DETAILS:brMain Level:br- Kitchenbr- Living Roombr- Dining Roombr- Full Bath with Shower/Tub and Laundrybr- Bedroom: Queen Bedbr- Bedroom: King BedbrbrUpper Level:br- Loft Space: Queen Sleeper Sofabr- Bedroom (Suite): Queen Bed, Attached Bath with Shower/Tubbr- Bedroom: Duo Bunk Bed, Twin Bunk Bedbr- Full Bath with Shower/TubbrbrLower Level:br- Den/Game Area with Bar: Queen Sleeper Sofabr- Full Bath with Showerbr- Bedroom: Queen BedbrbrDISCLAIMERS: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.brbrbrDOG 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 5

Bed

Bath 4

Bath

Sleep 14

Sleeps

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$504.27

/ Nightly
Private Vacation Home

Cozy Deep Creek Cabin w/ Hot Tub & Fireplace

Oakland, Maryland, United States

Name: Beary Relaxing | Bedrooms: 5 | Bathrooms: 4.5 | Sleeps: 10 | Access: Lake Area | Pets Not Permitted | MUST BE 28+ YEARS TO RENT | Free WIFI ProvidedbrbrDESCRIPTION:brWelcome to Beary Relaxing, a charming vacation rental nestled in the serene surroundings of Deep Creek. This cozy retreat offers a perfect blend of comfort and tranquility, making it an ideal choice for your next getaway. As you step inside, you'll be greeted by a warm and inviting atmosphere. The tastefully decorated living area features plush furnishings, creating a cozy space to unwind after a day of adventure. Curl up on the comfortable sofa and enjoy a movie night with your loved ones, or simply bask in the glow of the fireplace during colder evenings. The fully equipped kitchen is a haven for culinary enthusiasts, complete with modern appliances and ample counter space. Prepare delicious meals and gather around the dining table to savor them together. Step onto the deck to sip your morning coffee while listening to the sounds of birds chirping, or soak in the private hot tub and let your worries melt away. Conveniently located, Beary Relaxing offers easy access to a variety of outdoor activities. Whether you're interested in hiking, fishing, or renting a boat for the day to explore the lake, there's something for everyone to enjoy. Book your stay at Beary Relaxing and experience the perfect blend of comfort, serenity, and adventure. Create lasting memories with your loved ones in this idyllic vacation rental.brbrACCESS DETAILS:brNo additional details provided for this home.brbrCOMMUNITY/AREA DETAILS:brLocated in Timberlake Village, a tranquil community of Duplex Villas. The community enforces Garrett County's noise ordinance and quiet time from 11pm to 8am as required by TVRU's Licensing Ordinance.brbrLAYOUT DETAILS:brMain Level:br- Great Roombr- Kitchenbr- Dining Areabr- Bedroom: Queen Bed, Attached Bath with Shower/Tubbr- Powder RoombrbrUpper Level:br- Bedroom: Queen Bed, Attached Bath with Shower/Tubbr- Bedroom: Queen Bed, Attached Bath with ShowerbrbrLower Level:br- Den Areabr- Bedroom: Queen Bed, Access to Jack and Jill Bathbr- Bedroom: Queen Bed, Access to Jack and Jill Bath br- Full Jack and Jill Bath: Shower/Tubbr- Laundry AreabrbrDISCLAIMERS: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

Bed

Bath 4

Bath

Sleep 10

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Exceptional(17)

$276.65

/ Nightly
Private Vacation Home

Windy Acres | Dog Friendly + Hot Tub & Great Views!

Oakland, Maryland, United States

Get ready to escape to a destination like no other at Windy Acres. This stunning chalet-style log cabin located in Herrington Manor State Park offers a unique rustic charm that is perfect for those looking for a true mountain getaway to rejuvenate and unplug from the daily grind. Plus, we are pet-friendly! brStep inside to the warmth of the open-concept main living area and feel your stress fade away! Large windows flank the wood-burning stone fireplace and the smell of leather and wood transports you into a Yellowstone experience you won’t have the pleasure to enjoy elsewhere in Maryland!brTaxidermy mounts, wood accents and vintage flare complement the plush leather seating and serene views from the living area. The adjoining kitchen offers all the essentials you need and a large kitchen island for additional workspace that also serves as your eating area indoors. Lean in to having that stress free vacation and cook up simple hearty meals and one-pot wonders during the colder months. In the summer, dine al fresco on the large deck as you overlook the prairie of the local horse farm of Herrington Manor State Park.brUpstairs, you will find your private master suite with vaulted ceilings, queen-sized bed and luxurious modern bathroom with separate standing shower and soaking tub. You will wake up refreshed and ready for your next adventure in the great outdoors!brTwo additional bedrooms are located on the main level along with a full-sized bath. Both bedrooms provide a comfortable full-sized bed and tasteful decorations for a restful sleep. brKids and teens will feel right at home in their own bonus room on the lower level. This room features a full-sized futon along with twin bunks and a smart TV for plenty of late-night movie watching. The third bathroom is also located here and features a custom antique dresser vanity and vessel along with a standing shower.brExceptional outdoor living space will truly enhance your vacation! The deck is made for afternoon barbecues and peaceful mornings with your coffee and a good book. The seclusion of Windy Acres is perfect for connecting with your family and friends or simply soaking in the sounds of nature and spotting local wildlife. You will especially enjoy taking a dip in the hot tub under a star-filled sky without the city lights interfering. You may just catch a shooting star or two!brWithin a 15-minute drive, you can reach the best of the Deep Creek Lake area and the historic charm of downtown Oakland is a mere 3 miles away! Just minutes from the popular Swallow Falls State Park, venture down the road to view Maryland’s highest free-falling waterfall, Muddy Creek Falls! If you are an outdoor enthusiast, Windy Acres is the perfect cabin for you to explore Garrett County’s best sights and attractions!brHerrington Manor is a 365-acre state park with a 53-acre lake located at its heart. The park offers many outdoor activities to guests including swimming, canoeing, kayaking, biking, and hiking trails, tennis, and basketball courts, and more! Popular winter activities are cross-country skiing. Ski and snowshoe rentals are provided as conditions permit and fat tire bike rentals are offered year-round. brGet ready for the laid-back cabin lifestyle and outdoor adventures you’ve been seeking and reserve your stay in Deep Creek Lake at Windy Acres.
Bed 3

Bed

Bath 3

Bath

Sleep 11

Sleeps

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