Home Vacation Rentals By Owner In Oakland, MD

Showing 537 Of 537 Vacation Rentals
Slider Thumb

$368.0

/ Nightly
Private Vacation Home

Dog-friendly house on the lake, central AC, & EV charger

Oakland, Maryland, United States

A Million Dollar ViewbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrDon’t miss the stunning sunsets over the water at this two-story lakefront home, the perfect spot for your next family vacation.brbrBegin your days with morning meditation or a yoga session on the spacious back patio, adorned with a beautiful garden and a soothing water feature. Lounge on the high-end outdoor furniture beneath the oversized umbrella, enjoying the tranquility of the outdoors. Outdoor fun awaits with a private gas grill for summer cookouts and a firepit for winding down the night with laughter and drinks.brbrInside, there’s plenty of room for everyone to enjoy their own activities. The upstairs living area features wood beams and abundant natural light from skylights and panoramic windows that frame breathtaking views of the lake. Curl up in the window seat with a good book and admire the scenery between chapters. Meanwhile, the downstairs family room offers an oversized sectional, perfect for cozy movie nights or game sessions.brbrTHINGS TO KNOWbrbrbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: There is free parking available for 3 vehicles.brbrSecurity camera details: Security cameras covering the entryways of the home.brbrDock details: Boats are not allowed, but guests may use the provided two-person kayak.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 3

Bed

Bath 3

Bath

Sleep 5

Sleeps

Slider Thumb

$217.31

/ Nightly
Private Vacation Home

Romantic Getaway near Swallow Falls State Park in Maryland

Oakland, Maryland, United States

This luxurious suite rental is located on a farm near Swallow Falls State Park in Maryland, and can provide two guests with an unforgettable romantic getaway. The suite features a plush king-size bed and a private bathroom with a shower, a sink, and a toilet. Linens, towels, and toiletries are kindly provided. brbr brbrThe suite exudes comfort, providing guests with a place to relax and enjoy each other's company after a busy day exploring the best of what Maryland has to offer. A mini-fridge keeps the champagne cool, ready to be enjoyed in the spectacular Jacuzzi tub found by the fireplace, for an evening of romance. Wrapped around the building is a shared deck, where guests can enjoy a morning cup of coffee in the sunshine while taking in the views. brbr brbrJust steps out the door are 65 acres of peace and tranquility, and the hosts also organize activities such as yoga and contra dancing. For outdoor adventures, there a national parks and forests in every direction, so guests should pack their outdoor gear. For those wanting something a bit more cultural, Pittsburgh, Baltimore, and Washington D.C. are within driving distance. brbr brbrThere is free Wi-Fi at the property, along with free parking and a Tesla charging station available. Guests are welcome to explore the fields that sprawl across the property and interact with the horses that roam them. To de-stress, there is a hammock that guests can rock in and an open fire ready for marshmallow roasting under the starlit sky. For indoor down time, there is a collection of board games, books, and magazines that any guest can borrow. All suites have air conditioning, although they are rarely necessary thanks to the property's high altitude and cooler temperatures. Each room has a fireplace to keep guests warm and cozy.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

Slider Thumb
Exceptional(2)

$333.63

/ Nightly
Private Vacation Home

A Beautiful View | Pet-Friendly Bungalow + Lake Views!

Oakland, Maryland, United States

Welcome to our quaint bungalow just steps from the lake! brbrA Beautiful View is the perfect retreat for a small family or group of friends looking to experience Deep Creek Lake and we are pet-friendly! With 2 bedrooms and 1 baths, our property can comfortably accommodate up to 6 guests.brbrThough it may be small, the large windows within A Beautiful View will flood the space with light and the windows in the upstairs bedrooms offer beautiful lake views!brbrThe interior of our home is tastefully decorated with splashes of color throughout and updated furniture and linens help to make your stay at the lake comfortable.brbrOutside, you’ll enjoy being across the street from the lake and within walking distance of popular eateries like Firewater Kitchen & Bar where you’ll enjoy handcrafted cocktails and Lakeside Creamery for a cold, tasty treat. You can also enjoy backyard BBQs on the grill and dine out on the umbrella-covered picnic table if you prefer to stay home.brbrDuring the summer months, you will be in the middle of the action to enjoy lake activities like swimming, paddleboarding, and fishing and are a short drive away from Deep Creek Lake State Park where you can enjoy the only sandy beach in the area. During the winter months, you’ll be a 10-minute drive away from Wisp Resort where you can hit the ski slopes or just enjoy the view from the lodge.brbrA Beautiful View is ready to make your next trip to Deep Creek Lake a memorable one for you and your guests.
Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(49)

$255.72

/ Nightly
Private Vacation Home

Charming Lake Cottage with Hot Tub, Filtered Lake Views & Spacious Yard

Oakland, Maryland, United States

All Spruced UpbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrEscape to this inviting 3-bedroom, 2-bath lake cottage—the perfect getaway for family, friends, and furry family members. Comfortably sleeping up to 8 guests, this cozy retreat offers the ideal balance of relaxation, recreation, and convenience.brbrLocated just a short stroll from waterfront dining and marina, you’ll be perfectly positioned to enjoy everything Deep Creek Lake has to offer. Spend sunny days swimming or fishing at Deep Creek Lake State Park, or head to Wisp Resort for year-round adventure—from winter skiing, snowboarding, and tubing to summer mountain coasters and scenic chairlift rides. Don’t miss Swallow Falls State Park, where hiking trails lead to breathtaking waterfalls. There is also a nearby hidden “natural maze”—a local gem worth discovering.brbrAfter a day of outdoor fun, return to your private retreat to the deck or grill dinner and dine al fresco at the picnic table, and soak in the hot tub while taking in tranquil, filtered lake views. Inside, you’ll find a bright, updated interior featuring a TV in every room and a game and movie room for evening entertainment. brbrWhether you’re here to unwind by the lake or explore the mountains, this home offers the perfect blend of comfort, charm, and convenience.brBook your stay today and start making unforgettable memories at Deep Creek Lake!brbrThings to KnowbrCheck-in time: 4:00 p.m.Check-out time: 10:00 a.m.All guests shall abide by Vacasa’s good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.No smoking is permitted anywhere on the premises.4WD/traction is required in winter.Two dogs are welcome for a nightly fee There is a 13-night limit on reservations per local regulations, and reservations for more than 13 nights are prohibited and cannot be honored.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 3 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(20)

$556.79

/ Nightly
Private Vacation Home

Mountain-view home with hot tub, washer/dryer, central AC, fireplace

Oakland, Maryland, United States

Spacious Panoramic Deep Creek LodgebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThis spacious home sits on three peaceful acres with beautiful views of both the mountains and the water. As a guest, you'll enjoy membership at CARC, giving you access to a pool, hot tubs, and a gym.brbrInside, the home's warm and inviting atmosphere is complemented by high ceilings and large windows, making the space feel bright and airy. The open floor plan encourages togetherness, but when you seek a quiet moment, the deck offers a perfect retreat to soak in the views, or you can unwind in one of the well-appointed bedrooms.brbrThe kitchen features stainless steel appliances, wood cabinets, and a convenient breakfast bar. After gathering around the large dining table, relax in the cozy living room to watch a movie, or head to the deck for a soak in the hot tub under the stars.brbrAdditional highlights include a washer/dryer, a jetted tub in the primary bedroom, a spacious loft with extra sleeping space, and a ping pong table for some fun.brbrTHINGS TO KNOWbrGuests must use their own accounts to access streaming.brbrParking notes: There is free parking available for 8 vehicles.brbrSecurity camera details: This camera is pointing to the entrance of the driveway, in no way shows the home.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 5

Bed

Bath 6

Bath

Sleep 14

Sleeps

Slider Thumb
Exceptional(5)

$249.22

/ Nightly
Private Vacation Home

3-bed, charming modernized cottage tucked into wooded hillside in Deep Creek, MD

Oakland, Maryland, United States

Cozy up this winter at our charming, modernized cottage decorated for Christmas and tucked into the wooded hillside. brbrWith an open layout, stone fireplace, and plush furnishings, Pop-a-Top Inn is the place to return to after a busy day around the area. Located just minutes from multiple State Parks, fantastic restaurants, and the four season Wisp Resort, you’ll never run out of things to keep you entertained. Enjoy your morning coffee on the front or back deck, catch up on some reading on the upper level balcony, or curl up in front of the fireplace in the living room. Enjoy some swimming, fishing, or kayaking at the lake access point less than a quarter mile away or head out to see what all the area has to offer. Let the friendly competition play out over a round of mini golf or a couple laps around the go-kart track, or head to Honi Honi to sunbathe on their large lakeside yard while enjoying each others company. As the day winds down, make sure to stop a Creamery for a delicious treat before returning to the home! As the sun starts to set, gather in front of the glow and warmth of the campfire for hot dogs, s’mores and stories before drifting off to sleep in the plush and cozy beds. brbrIn the winter, hit the slopes for skiing and snowboarding or the state parks for cross-country skiing and snowshoeing. brbrTucked in the trees you’ll be immersed in the winter wonderland that is the snowy Deep Creek area! When you are finished with your cold and snowy adventures, allow the hot tub to soothe any aches and pains from the day. brbrFrom sunny summer days, to cozy winter nights, and every moment in between, Pop-a-Top is the place to be!brbrVirtual Tour: https://tour.TruPlace.com/property/1876/78010/
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(26)

$936.86

/ Nightly
Private Vacation Home

Beautiful lakefront home with hot tub, game room, washer/dryer & private dock

Oakland, Maryland, United States

Luxury LakebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThis stunning lakefront property with breathtaking views is located in the prestigious Blakeslee community on a quiet cove of Deep Creek lake, the perfect getaway for your group or family.brbrLocated just minutes from Wisp Ski Resort, Adventure Sports Center, and Downtown Oakland, you'll find endless activities and attractions nearby. Blakeslee community amenities include a clubhouse with a pool table, a heated indoor pool, and courts for basketball, tennis, and pickleball. Outdoor enthusiasts will love fishing, paddleboarding, and kayaking on the lake or taking advantage of the private dock with two wave runner/jet ski spots. The immaculately landscaped backyard is an oasis, featuring a hammock, porch swing, firepit, and stunning sunset views. After a day of activities, unwind in the private hot tub and let your cares melt away.brbrStep inside to be greeted by bright, sunlit spaces and a warm, welcoming ambiance. The living area boasts floor-to-ceiling windows, offering magnificent lake views, while the plush seating around the stone fireplace invites relaxation. The gourmet kitchen, with state-of-the-art stainless steel appliances and a floating island breakfast bar, is a dream for any chef. Enjoy meals or competitive board games at the formal dining table, and head to the second-floor game room for a fun Ping-Pong match.brbrEach of the spacious bedrooms ensures a restful night’s sleep, with en suite bathrooms for added convenience. The main bedroom offers a private entrance to the backyard, an electric fireplace, and a TV for personal relaxation. Kids will love their own bunk bed space, making it a special retreat just for them. Plus, you'll find washer/dryer units on both floors and a large mudroom, perfect for storing winter or ski gear.brbrCreate unforgettable memories at this one-of-a-kind lakefront retreat—an ideal setting for your next vacation.brbrTHINGS TO KNOWbrTo use streaming services, guests must log in with their own credentials.brAn outdoor shower is provided; please rinse off after coming back from the lake.brbrParking notes: There is free parking available for 6 vehicles.brbrDock details: There is a private 25-foot dock with a type A permit behind the home that guests may use for boats up to 26 feet or pontoons up to 30 feet. The water is about five feet deep, and guests must provide their own ropes or other equipment.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 4

Bed

Bath 5

Bath

Sleep 12

Sleeps

Slider Thumb
Exceptional(2)

Select Dates for Price

Spacious Lake Escape w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

Name: Camp CAJAR | Bedrooms: 5 | Bathrooms: 4 | Sleeps: 12 | Access: Lake Front | Pets Not Permitted | MUST BE 24+ YEARS TO RENT | Free WIFI ProvidedbrbrDESCRIPTION:brNestled among the trees, Camp CAJAR is a spacious and meticulously designed rental home that welcomes families, groups of friends, and anyone looking to get away from the hustle and bustle. The large open concept main level is great for entertaining, and the fully equipped kitchen is perfect for the culinary expert in the group. Step onto the large deck to breathe in the fresh mountain air as you sip your morning coffee and gaze at the lake views. On bright sunny summer days, the deck is also the perfect place to catch a tan and soak in the sun. Located along Lake Shore Drive, Camp CAJAR is close to all the action that Deep Creek has to offer. Just minutes from fantastic restaurants, a myriad of activities on and off the water, and the four-season Wisp Resort, you will never run out of things to do! There are two boat slips to park your boat or jet skis so you can access the lake throughout the day, then enjoy a soak in the bubbling hot tub which also has amazing lake views. In the evenings, gather around the fire pit for campfire stories, star gazing, and s’mores. On rainy days, head to the lower level for a gaming day with a shuffleboard table, an arcade game table, and dartboard or challenge your friends to a game of billiards in the game room off the main floor living room or watch a movie in front of the stunning stone fireplace. Whether you are looking for a trip of relaxation, adventure, or a little bit of both, Camp CAJAR has you covered! Book your stay today!brbrACCESS DETAILS:brLake Access and Dock are located down the path from the back of the home. Please note that docks are only guaranteed from Memorial Day through Labor Day.brbrCOMMUNITY/AREA DETAILSbrThis home is located on Lake Shore Dr. in 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/Tubbr- Bedroom: Queen Bedbr- Bedroom: Full Bedbr- Game RoombrbrUpper Level:br- Loft Areabr- Bedroom (Suite): King Bed, Attached Bath with ShowerbrbrLower Level:br- Den/Game Areabr- Bedroom: Full over Queen Bunk Bed, Access to Shared Bathbr- Full Bath with Showerbr- Bedroom (Suite): Queen 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 5

Bed

Bath 4

Bath

Sleep 12

Sleeps

Slider Thumb
Exceptional(8)

$284.1

/ Nightly
Private Vacation Home

Rustic hideaway with hot tub, pool table, wood fireplace, firepit - dog-friendly

Oakland, Maryland, United States

Nimba CabinbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNo matter the season, Nimba Cabin offers a peaceful wilderness retreat for you and your loved ones. Nestled near numerous outdoor recreation hotspots, your stay promises unforgettable memories. In winter, head to nearby Wisp Resort for excellent skiing and snowboarding. During warmer months, explore the beauty of Deep Creek Lake State Park, Swallow Falls State Park, Thousand Acres Lakeside Golf Club, and Deep Creek Lake itself.brbrBack at the cabin, continue enjoying the Maryland landscape with a soak in the hot tub, a cookout on the gas grill, or roasting marshmallows over the firepit under the stars.brbrInside, rustic charm meets modern convenience. The living room exudes cozy comfort with its stone-lined wood-burning fireplace, large smart TV, and oversized sofa. For even more space to relax, a second hangout room features a pool table, large TV, bar, and plenty of seating.brbrThe kitchen is well-equipped with stainless steel appliances and a spacious breakfast bar, perfect for whipping up meals and snacks to fuel your adventures.brbrAs evening falls, you’ll rest easy in the cozy bedrooms, each cooled by mini-split AC units and outfitted with soft linens for a comfortable night’s sleep.brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by Vacasa’s good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises. brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 4 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 3

Bed

Bath 4

Bath

Sleep 10

Sleeps

Slider Thumb
Exceptional(11)

$289.16

/ Nightly
Private Vacation Home

Tranquil lake retreat with private hot tub, fire pit, deck, & incredible views

Oakland, Maryland, United States

Lake DazebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThis magnificent multi-level townhome, nestled in the serene surroundings of Deep Creek Lake, offers an abundance of amenities and breathtaking views to inspire an unforgettable vacation.brbrPerfectly located for year-round outdoor fun, you'll find Wisp Resort less than five miles away, offering zip-lining and mountain biking in the summer and world-class skiing and snowboarding in the winter. Both Deep Creek Lake State Park and Swallow Falls State Park are within 10 miles, where you can enjoy boating, fishing, and hiking among peaceful waterfalls. For a more relaxed day, Oakland Golf Course provides leisurely rounds amidst scenic vistas, and you're just a short walk from local coffee shops and eateries.brbrStep inside this inviting retreat and feel right at home in the sunlit, open-concept living area. Plush seating, rustic decor, and deck access seamlessly blend comfort and nature. Stream your favorite movies on the smart TV or gather around the fireplace for board games and cocoa. The well-appointed kitchen features modern appliances and plenty of storage, making meal preparation effortless. Share home-cooked meals and laughter at the adjacent dining table, or head out to the patio to sip local brews while grilling the catch of the day in the sunshine.brbrAfter a day full of adventure, the cozy bedrooms welcome you with soft linens, additional TVs, and peaceful nature views. The primary en suite bathroom’s jetted tub offers a spa-like retreat, perfect for unwinding. As evening falls, relax in the private hot tub (complete with a movie screen and projector!) or gather around the firepit to roast s'mores under the stars, setting the stage for another day in this lakeside paradise.brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by Vacasa’s good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises. brbrParking notes: There is free parking available for 5 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(47)

$248.06

/ Nightly
Condo

Charming home with furnished deck & lake view - walking distance to shops

Oakland, Maryland, United States

High Mountain VillabrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNestled in the highly sought-after Trader's Landing community, High Mountain Villa is your perfect Deep Creek Lake escape. This charming retreat offers stunning seasonal views of the lake and surrounding mountains, with easy access to local favorites like Trader’s Coffeehouse, Brenda’s Pizzeria, and kayak rentals—just a short walk away.brbrAs you step into the condo, you’ll be greeted by an inviting living space designed for comfort and connection. The main level features a cozy living room with comfortable seating, a wood-burning fireplace, and large windows that offer breathtaking views of the surrounding scenery. Modern amenities abound, including multiple streaming TVs with cable, USB charging stations, and high-speed internet to keep you connected and entertained. The fully stocked kitchen makes it easy to whip up family meals or prepare snacks for your outdoor adventures.brbrThe main level also includes two queen bedrooms, offering restful accommodations for guests, along with a well-appointed bathroom.brStep outside to enjoy the fresh mountain air from comfortable seating on the deck, soak in the private hot tub, or fire up the propane grill for cookouts against a scenic backdrop. The outdoor area has a seating hot tub and an outdoor streaming TV.brBack inside, descend the spiral staircase to find a third bedroom with a full-sized bed and its own bathroom, providing additional privacy.brbrFamilies traveling with little ones will appreciate thoughtful touches like a high chair, baby gate, and Pack 'n Play. Partial air conditioning and a convenient washer/dryer add to the ease of your stay.brbrWhether you're enjoying the lake, hiking the trails, or skiing in the winter months, High Mountain Villa is the ideal home base for every season.brbrbrTHINGS TO KNOWbrThere is a 13 night limit on reservations per local regulations. Reservations over 13 nights are prohibited and cannot be honored.brbrParking notes: There is free parking available for 3 vehicles.brbrDock details: brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(7)

$806.0

/ Nightly
Private Vacation Home

Vibrant Lakeview Chalet w/ Huge Deck

OAKLAND, Maryland, United States

Name: Tamaqua Lodge | Bedrooms: 6 | Bathrooms: 5 | Sleeps: 15 | Access: Lake Front | Pets Not Permitted | MUST BE 24+ YEARS TO RENT | Free WIFI ProvidedbrbrColorful, vibrant, and fun! That’s Tamaqua Lodge- check out the large deck and stunning lakefront!brbrDESCRIPTION:brJoyful and uplifting, Tamaqua Lodge will elevate your spirits to new heights! Beautifully appointed rooms accented with eye-catching flair and style provide ample space for your family and friends. Although outstanding views can be seen throughout the interior of the home thanks to ample floor-to-ceiling windows, be sure to escape to your expansive deck to take full advantage of the mesmerizing view. Located along a quaint country lane and tucked against the tress, this lake home boasts an utterly ideal location, just minutes from restaurants, state parks, and other favorite mountain-lake activities. Tamaqua Lodge is a celebration of the beauty of western MD! Experience the magic for yourself-- book today!brbrACCESS DETAILS:brPrivate Lake Front with Dock on property. Please note that docks are only guaranteed from Memorial Day through Labor Day.brbrCOMMUNITY/AREA DETAILS:brLocated in the Paradise Heights 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): Queen Bed br- Bedroom: Queen Bedbr- Full BathbrbrUpper Level:br- Loft: Sitting Areabr- Bedroom (Suite): King Bed, Attached Bath with ShowerbrbrLower Level:br- Game Roombr- Bedroom (Suite): Queen Bed br- Bedroom: Duo Bunk Bedbr- Full Bathbr- Bedroom: Queen Bed brbrDISCLAIMERS: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.brbrDISCLAIMERS: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.brThere 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 6

Bed

Bath 5

Bath

Sleep 15

Sleeps

Slider Thumb
Exceptional(80)

$234.4

/ Nightly
Private Vacation Home

Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough River

Oakland, Maryland, United States

Still MeadowsbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrExperience the best of country living in this cozy, two-level Oakland cabin, nestled on a grassy property near Deep Creek Lake. With a private deck, firepit, air hockey table, and dog-friendly accommodations, this three-bedroom home is ideal for families and nature enthusiasts alike.brbrEnjoy nearby outdoor wonders, with Swallow Falls and the Yough River only a mile away. Spend your days hiking in Swallow Falls State Park, exploring the beach and boat launch at Deep Creek Lake State Park, or hitting the slopes at Wisp Resort, just six miles north.brbrBack at the cabin, unwind beneath the shade of mature trees on the deck, cook on the gas grill, and gather around the firepit for s’mores under the stars. Inside, you’ll find a well-equipped kitchen with stainless steel appliances, free WiFi, and a game room with air hockey to keep everyone entertained.brbrPlan your Oakland escape today and discover the scenic beauty of this Maryland gem!brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by Vacasa’s good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.br4WD/traction is required in winter.brThere is a 13-night limit on reservations per local regulations, and reservations for more than 13 nights are prohibited and cannot be honored.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 3 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(2)

$296.45

/ Nightly
Private Vacation Home

3 Bears Lodge | Enjoy a Private Hot Tub & Lake Access!

Oakland, Maryland, United States

Take a well deserved retreat to 3 Bears Lodge, located in the serene surroundings of Deep Creek Lake. This octagon-style home, situated in a tranquil community, beckons you with its charm and comfort. The private dock provides seamless lake access to indulge in swimming, fishing or kayaking. Picture perfect summer days can be spent at the community pavillion.brbrThis inviting getaway features three bedrooms, three full bathrooms and accommodates up to six guests. After a day filled with adventures, unwind i the private hot tub, perfect for soothing relaxation and even a bit of stargazing.brbrThe great room, bathed in natural light and offering enchanting lake views, creates a warm ambiance with comfortable furnishings and hardwood floors. Whether you're catching up on a good book or enjoying your favorite show on the Smart TV, the space is designed for ultimate comfort. Step out onto the spacious balcony from the main living room to savor scenic views and mountain air. An additional living room on the first floor, complete with a Smart TV and a covered patio, provides an additional retreat space.brbrThe fully equipped kitchen, featuring stainless steel appliances and granite countertops, invites culinary enthusiasts to create memorable meals shared with loved ones. With both eat-in and dining room seating, there's plenty space for everyone to gather and enjoy each other's company.brbrThe primary suite, located on the main level, offers a king-size bed, smart TV and picturesque lake views. The private bathroom includes a tub shower and an elegant granite countertop vanity. Two additional bedrooms on the first floor, each with queen-size beds and private updated bathrooms, ensure a comfortable stay for all.brbrConveniently located, 3 Bears Lodge is within ten to fifteen minutes from the area's best activities, attractions, restaurants and shops. Deep Creek Lake State Park, just four miles away, promises a day filled with playgrounds, sandy beaches, hiking trails and kayak rentals.brbrNo matter the season, Wisp Resort beckons with a variety of adventures, from disc golf and ziplines to skiing, snowboarding and snow tubing. For a more leisurely pace, historic downtown Oakland offers charming shops, antique stores, restaurants and museums.brbr3 Bears Lodge is not just a vacation home - it's a promise of cherished memories and special moments with family and friends. Secure your reservation today and begin the countdown to your Deep Creek experience.brbr*Please Note: A 4WD vehicle is required in winter months (November - March).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

Bed

Bath 3

Bath

Sleep 10

Sleeps

Slider Thumb
Exceptional(43)

$249.81

/ Nightly
Cottage

Quaint dog-friendly retreat near the lake w/ wood stove, gas grill, & large yard

Oakland, Maryland, United States

IncognitobrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrTucked away in peaceful seclusion and surrounded by lush foliage, this charming retreat offers the perfect escape for those seeking tranquility while staying close to all the action. Start your mornings and end your evenings by the warmth of the wood stove, sipping your favorite beverage as you fully embrace vacation mode. The full kitchen, complete with a cozy breakfast nook, is perfect for whipping up home-cooked meals before heading out for a day of adventure. After a fun-filled day, the inviting living area provides a great spot to unwind, with free WiFi, cable, and four flatscreen TVs offering plenty of entertainment. For a more rustic evening, gather around the firepit under a starlit sky.brbrWhat's nearby: Despite its secluded feel, this home is ideally located near all that Deep Creek Lake has to offer. Spend your summer days swimming, fishing, boating, or hiking at Deep Creek Lake State Park, or enjoy dining at one of the many lakeside restaurants. For a night out, catch a movie at Garrett 8 Cinemas or head to McHenry for even more fun and entertainment.brbrThings to know:brWood stove (wood not provided)br4WD/traction is required in winter.br* Please note that this home has a Ring doorbell security camera that is pointed out at the front yard.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 3 vehicles.brbrSecurity camera details: The home has a Ring door bell camera that is pointed at the front yardbrbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(9)

$284.67

/ Nightly
Cabin

Cubs Den - Hot Tub- Walk to Lake-Fire Pit -Kayaks

Oakland, Maryland, United States

Summary:brRustic cabin livin’ in a great location. Walk down the hill to public access on Deep Creek Lake! Just minutes from Wisp Resort! brBring your cubs or have a couples getaway at a charming, cozy log cabin nestled in the woods—yet minutes from Wisp and all fun Deep Creek Lake activities. brOur Cub’s Den has 3 bedrooms that can sleep a total of 8. It is completely renovated and remodeled, and has a brand new Hot Tub!brbrThe Space:brThis is a charming, newly remodeled cabin (renovated March, 2021). Literally every wall, floor, fixture and appliance is brand new. The 2 bedrooms downstairs are queen and full. Uostairs has a queen and two cubby twin beds. There is one full bath with a bathtub and tile shower. Granite kitchen with stainless steel appliances. Fire pit in back and hot tub on front porch with peekaboo view of lake. Walk down to public lake access and take one of our kayaks!brbrGuest Access:brYou will be alone and have access to everything. You can also borrow the two kayaks and take down to the lake.brbrThe Neighborhood:brJust a couple houses on the street. Wooded area close to the lake.brbrGetting Around:brThere is no public transportation in Garrett County. brbrI’m the winter 4x4 is high key recommended. The street getting yo to the house is steep.brbrOther Things to Note:brThis is a No-Smoking property. brbrNo loud music past 10p. brbrMaximum of 8 sleeping capacity. brbrPlease no glass around hot tub. Please clean grill after each use.brbrInteraction with Guests:brYou are alone. Your host, Drew and his team will be available by messaging through the Airbnb app.
Bed 3

Bed

Bath 1

Bath

Sleep 8

Sleeps

Home Most popular vacation rentals in Oakland