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12 available vacation rental offers
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Best Vacation rentals and Airbnb offers in Oakland, MD
8.6 6 reviews
Oakland, MD
07/01 – 10/01
$542/nighttotal: $49864 (92 )
328 M² House ∙ 6 Bedrooms ∙ 14 Guests
6 1
house , Oakland
Fir Reel, a spacious chalet near Deep Creek Lake in Maryland, provides easy access to Wisp Resort and Deep Creek Lake State Park, a short 5-10 minute drive away. This 3,520-square-foot vacation home boasts six bedrooms, five bathrooms, and sleeps fourteen guests, featuring a fully equipped kitchen, multiple primary suites, a lower-level family room with games, upper and lower decks with a hot tub, and a gas grill.
9.6 23 reviews
Oakland, MD
08/09 – 08/11
$330/nighttotal: $660 (2 )
A314 Studio & Loft Standard View
1 2
studio , Deer Park
A314 Studio & Loft, a 560-square-foot Oakland apartment, is located 45 miles from Morgantown Municipal Airport, offering convenient access to Deer Park while noting the travel distance. This one-bedroom unit features a kitchenette with a fridge, microwave, and dishwasher, plus a terrace, sauna, fitness center, and free parking; it comfortably sleeps one.
Oakland, MD
08/09 – 08/11
$303/nighttotal: $606 (2 )
Charming 3br Condo - Hot Tub - Lake View
3 2
house , Oakland
This vacation home in Oakland offers stunning lake views and is located approximately 43 miles from Morgantown Municipal Airport. This 1500 square foot residence features 3 bedrooms, 4 bathrooms, a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a jacuzzi, and a garden, accommodating up to 15 guests.
10 1 review
Oakland, MD
07/10 – 07/12
$424/nighttotal: $848 (2 )
48 M² Cabin ∙ 2 Bedrooms ∙ 5 Guests
2 2
cabin , Oakland
This cabin is located near Swallow Falls and the Youghiogheny River, offering direct hiking access and a short drive to Deep Creek Lake area attractions. This 520 square foot retreat accommodates up to 5 guests with 2 bedrooms, featuring a private hot tub, gas grill, gas fireplace, and a firepit area.
10 1 review
Oakland, MD
07/01 – 10/01
$146/nighttotal: $13432 (92 )
Cozy Home In The Mountains
3 1
apartment , Terra Alta
This Terra Alta apartment is located under 30 miles from Deep Creek Lake and just minutes from numerous state parks, offering a peaceful retreat with a genuine local experience. This 3-bedroom, 2-bathroom rental accommodates up to 5 guests and features a garden, a pond for fishing, a shooting range, and expansive deck space, with internet, air conditioning, and a full kitchen including a dishwasher and microwave.
8.7 44 reviews
Oakland, MD
08/09 – 08/11
$509/nighttotal: $1018 (2 )
Hidden Treasure
4 2
house , Oakland
Hidden Treasure is a vacation rental located in Oakland, Maryland, just a short drive from the Morgantown Municipal Airport and close to the Maryland region. The property has received very good user ratings, and excellent ratings for location and cleanliness. The house has four bedrooms and is 870 square feet in size. Guests can enjoy amenities such as a private patio, free private parking, a fully equipped kitchen, laundry facilities, satellite TV, and access to nearby skiing and cycling opportunities.
Oakland, MD
08/09 – 08/11
$332/nighttotal: $664 (2 )
A-frame Cabin - Minutes From Wisp
2 2
chalet , Oakland
This Oakland, Maryland mountaintop cabin sits on a one-acre forested lot, 5–15 minutes from Deep Creek Lake and Wisp Resort. The 1810-square-foot A-frame home features two bedrooms, one bathroom, and sleeps five, offering a fully equipped kitchen, a propane fireplace, smart TV, and pet-friendly accommodations (fee applies, limit two pets).
10 1 review
Oakland, MD
07/10 – 07/12
$497/nighttotal: $994 (2 )
Dizzy's Den--5 Minute Walk To Lake Access-rentals--formerly The "Love Shack"
3 2
chalet , Deer Park
This Deer Park cabin, centrally located in Yellowstone Village, is a 1000 square foot, 3-bedroom, 1-bathroom log home accommodating up to 6 guests, situated a short drive from Deep Creek Lake State Park and WISP, and within walking distance to the lake and a very short drive to restaurants and groceries. This pet-friendly accommodation features a newly renovated kitchen with a microwave and dishwasher, air conditioning, a year-round six-person hot tub, a gas outdoor fire pit, a wood-burning fireplace with free firewood, a loft bonus room, and a laundry center with a washer and dryer, with provided amenities including sheets, towels, kitchen spices, oils, bath products, and firewood.
9.8 38 reviews
Oakland, MD
07/10 – 07/12
$370/nighttotal: $740 (2 )
Lovely Terra Alta Cabin < 1 Mi To Alpine Lake
3 2
cabin , Terra Alta
This three-bedroom vacation home near Terra Alta, West Virginia, is conveniently located approximately 40 miles from Morgantown Municipal Airport. This 1500-square-foot cabin sleeps up to 10 guests and boasts a fully equipped kitchen with dishwasher, in-house laundry, cable TV, free Wi-Fi, a private garden, and a tennis court.
8.8 11 reviews
Oakland, MD
07/10 – 07/12
$371/nighttotal: $742 (2 )
Bearadise 3br W/loft Cabin W/ Game Room, Fire Pit & Resort Amenities
2 2
cabin , Terra Alta
This lakefront lodge in Terra Alta, West Virginia, is conveniently located within 12 miles of Cranesville Swamp Preserve, Cranesville Swamp Natural Area, Herrington Manor State Park, and Herrington Manor Recreation Area Reservoir. This four-bedroom, two-bathroom vacation rental sleeps up to ten guests and boasts a fully equipped kitchen, indoor pool, terrace, and BBQ grills, perfect for enjoying the nearby Glades Park.
9.4 12 reviews
Oakland, MD
08/09 – 08/11
$244/nighttotal: $488 (2 )
A118 Studio Standard View
1 2
studio , Deer Park
A118 Studio, a pet-friendly apartment in Oakland, offers convenient access to Deer Park and is located 45 miles from Morgantown Municipal Airport. This 380-square-foot unit features one bedroom, one bathroom, a kitchenette with a dishwasher and microwave, a private terrace, free parking, and access to a fitness center, sauna, and spa.
10 2 reviews
Oakland, MD
07/10 – 07/12
$465/nighttotal: $930 (2 )
Mountainside Cabin 51r-dog Friendly
1 2
cabin , Accident
This McHenry cabin rental near Deep Creek Lake in Accident, Maryland, offers easy access to Deep Creek Lake State Park and Wisp Resort. The 580-square-foot duplex suite sleeps six, features two queen beds, a pull-out couch, a kitchenette, a gas fireplace, and a balcony; pets are welcome.
Choose the Right Family-Friendly Vacation Rentals in Oakland, MD
These kid-friendly vacation rentals in Oakland, MD keep you close to top city attractions for a stress-free family vacation.
8.6 86 reviews
Oakland, MD
08/09 – 08/11
$578/nighttotal: $1156 (2 )
Cedarwoods
3 2
house , Oakland
This golf vacation home in Mountainside is conveniently located 1.4 miles from Deep Creek Lake and within 6 miles of popular attractions like Deep Creek Lake State Park and Funland, in the scenic Mountainside district, offering stunning views. With a very good user rating, this house has 3 bedrooms and 1550 square feet of floor area. It features a fully equipped kitchen, air conditioning, a Jacuzzi, a terrace, a garden, a spa, a restaurant, a fitness center, a tennis court, and parking.
10 3 reviews
Oakland, MD
07/10 – 07/12
$432/nighttotal: $864 (2 )
Minutes To The Wisp, Private, Kid & Pet Friendly Ranch
3 2
apartment , Oakland
This 1190 sq ft, 3-bedroom, 2-bathroom apartment in Oakland accommodates up to 7 guests and features a kitchen with a fridge and microwave, internet, and parking. The property offers a garden, spa, and is family and pet-friendly, located 3 miles from Deep Creek Lake and Fork Run Recreation Area, with winter sports opportunities nearby.
10 1 review
Oakland, MD
07/10 – 07/12
$588/nighttotal: $1176 (2 )
120 M² Cabin ∙ 3 Bedrooms ∙ 8 Guests
3 2
cabin , Swanton
Camp Valentine is a secluded wooded cabin located in Swanton, offering peace and quiet just minutes from the state park, local dining, and area attractions. This 1290 square foot cabin accommodates up to 8 guests with 3 bedrooms, features a full kitchen, a swimming pool, a jacuzzi, a fireplace, and a deck with a grill, and requires a 4WD vehicle for winter access.
9.6 24 reviews
Oakland, MD
07/10 – 07/12
$951/nighttotal: $1902 (2 )
Happyplace Hideaway
4 2
house , Accident
This four-bedroom cottage located in Accident is perfect for a family getaway or a group of friends looking for a relaxing retreat. The cottage is situated in the scenic McHenry district, offering stunning views of the surrounding mountains and forests. It is also just a short drive from Lodestone Golf Club (1.1 mi) and Deep Creek Lake (1.6 mi). The cottage has an excellent user rating, location rating, and cleanliness rating. It features a private outdoor pool and spa tub, a spacious balcony, a cozy fireplace, and a fully equipped kitchen. The cottage also has free WiFi, air conditioning, a tennis court, and parking.
Best Oakland, MD vacation rentals with parking
9.2 13 reviews
Oakland, MD
07/10 – 07/12
$410/nighttotal: $820 (2 )
105a Efficiency One Bath
1 2
house , Deer Park
This Deer Park house is located in Oakland, a district just 45 miles from Morgantown Municipal Airport, offering easy access to the area's attractions. Guests consistently rate this home excellent for its location, cleanliness, and overall experience. The house features a separate bedroom and seating area, providing both privacy and space for relaxation. Amenities include a kitchen with a fridge and microwave, a fireplace, air conditioning, a terrace and balcony, a swimming pool, a jacuzzi, a sauna, a fitness center, and free parking.
10 27 reviews
Oakland, MD
07/10 – 07/12
$493/nighttotal: $986 (2 )
Cozy Cabin With Hot Tub, Fire Pit, Game Room -Near Deep Creek Lake
3 2
cabin , Gorman
This Gorman, Oakland cabin rental is conveniently located within 6 miles of Loch Lynn Heights Town Hall, Bayard Park, and Mountain Lake Park Town Hall, and 9 miles from the Baltimore and Ohio Railroad Station and Broadford Park. This three-bedroom, two-bathroom getaway sleeps six and boasts a fully equipped kitchen, Jacuzzi, private garden with barbecue grills, tennis court, free Wi-Fi, and a patio; enjoy nearby hiking and explore the area's historical sites.
10 7 reviews
Oakland, MD
08/09 – 08/11
$262/nighttotal: $524 (2 )
A122 Studio Standard View
1 2
studio , Deer Park
This Deer Park studio apartment, located approximately 45 miles from Morgantown Municipal Airport, offers convenient access to the area. The 380-square-foot unit features one bedroom, one bathroom, a kitchenette with a fridge, microwave, and dishwasher, plus a private terrace, sauna, and access to a fitness center and free parking.
Oakland, MD
07/01 – 10/01
$676/nighttotal: $62192 (92 )
Beautiful Cabin With Lake Access, Hot Tub, And All The Amenities
4 1
apartment , Deer Park
This Deer Park lodge is located in Oakland's Paradise Point neighborhood, offering private Deep Creek Lake access and proximity to Wisp Resort. This 4-bedroom, 3-bathroom accommodation sleeps 10 guests and features a fully equipped kitchen with granite counters, a wood-burning fireplace, a hot tub, and an indoor shuffleboard table.
Frequently Asked Questions about vacation rentals in Oakland, MD
What are some interesting places to visit in or near Oakland, MD?
You should definitely check out the Garrett County Historical Society Museum for a look into local history. If you're looking for some natural beauty, there are some great spots nearby like the Deep Creek Lake State Park and the Swallow Falls State Park, which features a 53-foot waterfall. If you're looking for something unique, check out the Oakland Arts Center which features rotating exhibits and local art.
What are the best Airbnb and vacation rentals in Oakland, MD?
Which walking or cycling routes are the best in Oakland, MD?
The Great Allegheny Passage is a popular choice for cyclists and walkers. It's a 150-mile rails-to-trails route that runs right through Oakland. There's also the scenic Blackwater Trail, a 10-mile paved path that follows the Blackwater River. If you're looking for something shorter, there's a nice walking loop around the Oakland Lake.
What sports or outdoor activites can visitors enjoy in and around Oakland, MD?
You can find all kinds of outdoor activities here. Deep Creek Lake is a great place for boating, swimming, and fishing. The area is also popular for hiking, biking, and kayaking. In the winter, you can go skiing at Wisp Resort. There are also a few golf courses in the area.
What are the best vacation rentals with a pool in Oakland, MD?
What other towns or cities can be easily accessed from Oakland, MD?
You can easily get to Cumberland, MD, which is about 20 miles away. It's a bigger city with more restaurants and shops. You can also get to the city of Frostburg, MD, in about 30 minutes. It's a nice small town with a university and some historic buildings. If you want to go further, you can get to the city of Hagerstown, MD, in about an hour and a half.
What are the best rentals for families and kids in Oakland, MD?
What amenities are commonly available in vacation rentals in Oakland, MD?
Most vacation rentals here will have basic amenities like a kitchen, bathroom, and bedrooms. Many also come with things like a washer and dryer, a fireplace, and a deck or patio. Some rentals even have hot tubs or swimming pools. It really depends on what you're looking for.
What are the best rentals or Airbnbs with a jacuzzi in Oakland, MD?
What time of year is best to rent a vacation rental Oakland, MD?
The best time to visit is really dependent on what you want to do. If you're looking for warm weather and swimming, the summer months are perfect. If you're looking for fall foliage, September and October are beautiful. If you enjoy winter activities like skiing, then December through February is the best time to come.
Destinations nearby
Guest-Favorite Vacation Rentals with a Terrace in Oakland, MD
Elevate your stay in Oakland, MD with a vacation rental featuring a private balcony and stunning city skyline views.
8.7 6 reviews
Oakland, MD
07/10 – 07/12
$394/nighttotal: $788 (2 )
106a Efficiency One Bath
1 2
house , Deer Park
This Deer Park vacation home is conveniently located 45 miles from Morgantown Municipal Airport in Oakland, offering easy access to area attractions. This one-bedroom, one-bathroom rental boasts a private balcony, indoor pool, sauna, fully equipped kitchenette, free Wi-Fi, and free private parking.
8.4 2 reviews
Oakland, MD
08/09 – 08/11
$403/nighttotal: $806 (2 )
234 M² House ∙ 4 Bedrooms ∙ 10 Guests
4 2
house , Oakland
Home Sweet Cabin, located in a quiet Oakland, Maryland cove near Wisp Resort and Swallow Falls State Park, offers easy access to Deep Creek Lake State Park. This 2,520-square-foot house features four bedrooms, two bathrooms, sleeps ten guests, and includes a game room, expansive wraparound deck, outdoor hot tub, and in-ground swimming pool, plus a provided State Park pass for summer access to local parks.
9.2 4 reviews
Oakland, MD
08/09 – 08/11
$457/nighttotal: $914 (2 )
170 M² House ∙ 4 Bedrooms ∙ 8 Guests
4 2
house , Oakland
The Butterfly Retreat, a Deep Creek Lake house rental in the Mountainside community, is a 10-minute drive from Wisp Resort and close to local shops and restaurants. This 1820-square-foot vacation home offers four bedrooms, two bathrooms, a bonus room with games, two living areas, a fully equipped kitchen, a private hot tub, and accommodates up to eight guests, with access to community amenities including tennis courts.
Oakland, MD
08/09 – 08/11
$405/nighttotal: $810 (2 )
Pet-friendly, Hot Tub, Beautiful Mountain Cabin
3 2
apartment , Oakland
This cabin, located in Yough Mountain Resort, is a 20-minute drive from Deep Creek Lake and Oakland, offering a wooded setting with direct access to ATV and snowmobile trails, and is 9 miles from Swallow Falls State Park and 7 miles from Herrington Manor State Park. This 1100 square foot rental accommodates up to 8 guests with 3 bedrooms, 1 bathroom, a full kitchen, a private hot tub, an indoor fireplace, an outdoor fire pit, a playground, and an on-site washer and dryer.
Top-Rated Pet-Friendly Vacation Rentals in Oakland, MD
Discover pet-friendly vacation rentals in Oakland, MD that prioritize comfort for both you and your dog.
9.0 2 reviews
Oakland, MD
08/09 – 08/11
$617/nighttotal: $1234 (2 )
Owl's Nest
3 2
house , Oakland
Owl House, located in Oakland, offers mountain views and is 42 miles from Morgantown Municipal Airport. This three-bedroom house sleeps eight, boasts 1320 square feet of space, a fully equipped kitchen, a jacuzzi, and a relaxing patio; nearby skiing opportunities are available.
9.3 22 reviews
Oakland, MD
07/10 – 07/12
$260/nighttotal: $520 (2 )
Pet Friendly Cabin Close To Alpine Lake
1 2
cabin , Terra Alta
This pet-friendly cabin near Alpine Lake in Terra Alta, West Virginia offers easy access to seasonal kayaking, swimming, and fishing. Sleeping up to eight guests, this three-bedroom, two-bathroom lodge boasts a fully equipped kitchen with dishwasher, a private garden, swimming pool, and parking; firewood and charcoal are not provided.
9.9 75 reviews
Oakland, MD
07/10 – 07/12
$420/nighttotal: $840 (2 )
Centrally Located | Mountain View | Private 1 Acre
1 2
cabin , Oakland
Red Run Retreat is a private cottage located near Oakland, Maryland, within easy driving distance of Swallow Falls State Park, Wisp Resort, and Deep Creek Lake. This cottage has consistently received excellent ratings for its location, cleanliness, and overall experience. This three-bedroom, two-bathroom cottage can comfortably accommodate up to eight guests. The cabin offers a fully equipped kitchen, air conditioning, a garden, parking, and outdoor living spaces, including a porch, deck, and firepit.
Oakland, MD
07/10 – 07/12
$550/nighttotal: $1100 (2 )
Mountainside Cabin 51l
1 2
cabin , Accident
This McHenry, Maryland cabin is located near Deep Creek Lake and Deep Creek Lake State Park, providing easy access to Wisp Resort and various outdoor activities. The 580-square-foot duplex suite sleeps six, featuring two queen beds, a pull-out couch, a gas fireplace, kitchenette, 55" Smart TV, and a private garden; pets are welcome.
