Best apartment offers in Oakland, MD

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Oakland, MD apartments
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12 Holiday apartments Oakland, MD

Best family friendly Oakland, MD Holiday Apartments and Self Catering Accommodations

Among the 4 accommodations in Oakland, MD, here are the 4 best family friendly holiday apartments

Villages Of Wisp 33 Winding Way | Lake Access + Hot Tub - Oakland, MD
8.4 5 reviews
Oakland, MD
23/06 – 25/06
314 €/nighttotal: 628 € (2 )

Villages Of Wisp 33 Winding Way | Lake Access + Hot Tub

2 4
apartment , Accident
This three-storey townhome in McHenry, Maryland, offers ski-in/ski-out access (weather permitting) to Wisp Resort and is situated near Deep Creek Lake.
The 143 square metre property sleeps up to 10 guests, boasting three bedrooms, three bathrooms, a fully equipped kitchen with dishwasher, a hot tub, and multiple Smart TVs; nearby attractions include Deep Creek Lake State Park and Swallow Falls State Park.
Chill, Play & Enjoy Nature & Memories - Oakland, MD
9.3 40 reviews
Oakland, MD
23/06 – 25/06
421 €/nighttotal: 842 € (2 )

Chill, Play & Enjoy Nature & Memories

2 4
apartment , Swanton
This Swanton lakeside property, situated within 3.2km of Deep Creek Lake and Thousand Acres Lakeside Golf Course, and 19.3km from Deep Creek Lake State Park and the Savage River, offers stunning water views and easy access to local attractions.
This 112 square metre dwelling boasts two bedrooms, one bathroom, sleeps eight guests, and includes a fully equipped kitchen, jacuzzi, terrace, garden, spa, parking, and free Wi-Fi; nearby activities include an on-site arcade/game room and BBQ facilities.
Value Stay*lots Of Privacy W Hot Tub-firepit-games - Oakland, MD
Oakland, MD
24/06 – 28/06
568 €/nighttotal: 2272 € (4 )

Value Stay*lots Of Privacy W Hot Tub-firepit-games

5 2
apartment , Oakland
This Oakland dwelling is located in a peaceful area, a short drive from Deep Creek Lake and Wisp Resort, offering convenient access to outdoor pursuits.
This 232 square meter flat accommodates up to 14 guests, featuring a hot tub, garden, two indoor fireplaces, an outdoor fire pit, and WiFi, with free on-site parking.
Cabin In The Woods, Hot Tub, Pool Table, Fire Pit, Swing Set - Oakland, MD
10 40 reviews
Oakland, MD
24/06 – 28/06
417 €/nighttotal: 1668 € (4 )

Cabin In The Woods, Hot Tub, Pool Table, Fire Pit, Swing Set

4 2
apartment , Deer Park
This family-friendly house is located in the mountains of Oakland, just 1.8 kilometres from Deep Creek Lake, and within a 14.5 kilometre radius of Funland, Deep Creek Lake State Park, the Youghiogheny River, and Garrett Regional Medical Center. The property has received excellent user ratings.
This 255 square metre house has four bedrooms and three bathrooms, comfortably accommodating up to 10 guests. The house offers a range of amenities, including a fully equipped kitchen, a jacuzzi, a terrace, a garden, parking, and a fireplace, as well as family-friendly features like a games room and a barbecue.

Best Oakland, MD holiday apartments with a kitchen

Saved By The Summit | Hot Tub, Game Tables, Great Location - Oakland, MD
10 1 review
Oakland, MD
27/06 – 04/07
426 €/nighttotal: 2982 € (7 )

Saved By The Summit | Hot Tub, Game Tables, Great Location

5 1
apartment , Accident
This five-bedroom residence is situated in McHenry, placing it within easy reach of Deep Creek Lake and Wisp Resort, with Funland and the Baltimore and Ohio Railroad Station also in the vicinity.
This spacious 324 square metre holiday home, accommodating up to 12 guests, features a fully equipped kitchen, multiple sitting areas, a downstairs family room with entertainment options, and outdoor amenities including a private hot tub and gas grill, all ideal for exploring the nearby lake and recreational activities.
Peaceful Rustic Chalet W/ Hot Tub & Fireplace - Oakland, MD
9.1 58 reviews
Oakland, MD
23/06 – 25/06
632 €/nighttotal: 1264 € (2 )

Peaceful Rustic Chalet W/ Hot Tub & Fireplace

5 4
apartment , Oakland
This five-bedroom holiday home is located just under a kilometre from Deep Creek Lake and three kilometres from Swallow Falls State Park, offering a peaceful retreat surrounded by natural beauty. The property has received excellent ratings for its location, cleanliness, and overall experience.
The 270 square metre home comfortably accommodates up to 14 guests and features a fully equipped kitchen, a spa, a terrace, a garden, parking, and a fireplace, providing ample opportunity for relaxation and entertainment.
708h Studio Loft One Bath - Oakland, MD
9.7 6 reviews
Oakland, MD
23/06 – 25/06
253 €/nighttotal: 506 € (2 )

708h Studio Loft One Bath

1 4
studio , Deer Park
This studio apartment is located in Oakland, California, just a short distance from Deer Park, offering easy access to the area's attractions. It consistently receives excellent ratings for its location, cleanliness, and overall guest experience.
The studio features a separate bedroom and seating area, providing a comfortable space for relaxation. Guests can enjoy a range of amenities including a private terrace and balcony, a swimming pool, a jacuzzi, a sauna, and a fitness centre, ensuring a relaxing and enjoyable stay.
A214 Studio Standard View - Oakland, MD
8.9 2 reviews
Oakland, MD
09/08 – 11/08
258 €/nighttotal: 516 € (2 )

A214 Studio Standard View

1 2
studio , Deer Park
This Oakland apartment is situated approximately 72 kilometres from Morgantown Municipal Airport, a location noted for its proximity to various attractions in the surrounding area, though not specifically Deer Park.
This 35-square-metre self-catering studio sleeps one, boasting a kitchenette with dishwasher, microwave and fridge, a balcony, terrace, sauna, fitness centre, parking, and free Wi-Fi and private parking.

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Best Oakland, MD holiday apartments with air conditioning

A213 Studio Lake View - Oakland, MD
Oakland, MD
09/08 – 11/08
286 €/nighttotal: 572 € (2 )

A213 Studio Lake View

1 2
studio , Deer Park
This studio apartment is situated in Deer Park, approximately 72 kilometres from Morgantown Municipal Airport.
This 35 square metre self-contained apartment offers a fully equipped kitchenette, air conditioning, complimentary WiFi, and on-site parking, with a restaurant and fitness centre available for guest use.
License To Chill | Lake Access + Outdoor Space - Oakland, MD
8.4 5 reviews
Oakland, MD
27/06 – 04/07
440 €/nighttotal: 3080 € (7 )

License To Chill | Lake Access + Outdoor Space

5 1
apartment , Swanton
This five-bedroom Waterfront Greens holiday home in Swanton is situated 0.5km from Deep Creek Lake and 2.6km from Deep Creek Lake State Park, with Thousand Acres Lakeside Golf Course approximately 14.5km away.
The 307 square metre property boasts a Jacuzzi, terrace, garden, parking, and a fully equipped kitchen including a fridge, microwave, and dishwasher; it sleeps families or groups and offers free Wi-Fi.
A318 One Bedroom & Loft Standard View - Oakland, MD
8.5 2 reviews
Oakland, MD
10/07 – 12/07
311 €/nighttotal: 622 € (2 )

A318 One Bedroom & Loft Standard View

1 2
apartment , Deer Park
The A318 One Bedroom & Loft Standard View is located in Oakland, a short distance from Deer Park and approximately 45 miles from Morgantown Municipal Airport. This accommodation has received very good user ratings and excellent ratings for both location and cleanliness.
The apartment offers a separate bedroom and loft, providing additional space and privacy for up to 6 guests. It comes with a fully equipped kitchenette, free Wi-Fi, air conditioning, a terrace, a garden, a sauna, a fitness centre, and free private parking.
Private Unit On Farm With Kitchen &  Balcony - Oakland, MD
9.8 130 reviews
Oakland, MD
10/07 – 12/07
189 €/nighttotal: 378 € (2 )

Private Unit On Farm With Kitchen & Balcony

1 2
apartment , Oakland
The Herrington Suite is a private apartment located on a 65-acre inn and retreat centre just 1.5 kilometres from Deep Creek Lake, offering a peaceful farm setting with views of the surrounding countryside. The suite is highly rated by guests, achieving excellent scores for cleanliness, location and overall experience.
The apartment has one bedroom and one bathroom, accommodating up to two guests. The suite includes a full kitchen, a sitting area with an electric fireplace, a king-sized bed, a private bathroom with a jetted tub and walk-in shower, a balcony overlooking the pond, and access to a garden, parking, and free Wi-Fi.

Best pet-friendly Oakland, MD holiday apartments

Among the 4 accommodations in Oakland, MD, here are the 4 best pet friendly holiday apartments

Rustic 3br Farmhouse - Fire Pit- Oakland - Oakland, MD
Oakland, MD
10/07 – 12/07
202 €/nighttotal: 404 € (2 )

Rustic 3br Farmhouse - Fire Pit- Oakland

3 2
apartment , Oakland
Still Meadows is a secluded farmhouse retreat located in the tranquil hills of Oakland, Maryland, offering sweeping mountain views just a short drive from the town's amenities. This pet-friendly cottage for six guests spans 73 square metres and features three bedrooms, a full kitchen, a wood-burning fire pit, and a propane grill, with 4-wheel drive recommended for access.
Cozy Dog Friendly Cabin Near State Park W/ Hot Tub - Oakland, MD
9.6 7 reviews
Oakland, MD
23/06 – 25/06
550 €/nighttotal: 1100 € (2 )

Cozy Dog Friendly Cabin Near State Park W/ Hot Tub

3 4
apartment , Oakland
This luxurious lakeside property near Oakland, Maryland, is situated less than 1.6km from the Youghiogheny Wild River Natural Environmental Area and Youghiogheny River, and under 5km from Swallow Falls State Park.
This 265 square metre house boasts three bedrooms, three bathrooms, sleeps up to ten guests, and features a Jacuzzi, tennis court, and free Wi-Fi, alongside access to on-site barbecue grills and laundry facilities.
Elegant Home Away: Hot Tub/game Room/kid-friendly - Oakland, MD
9.8 47 reviews
Oakland, MD
24/06 – 28/06
514 €/nighttotal: 2056 € (4 )

Elegant Home Away: Hot Tub/game Room/kid-friendly

1 2
apartment , Oakland
This four-bedroom, three-bathroom dwelling is situated near Oakland, Maryland's golf course, under 8 kilometres from Deep Creek Lake and a short drive from Wisp Ski Area.
The spacious property, boasting a private office, jacuzzi, fitness centre and extensive recreational amenities including a three-hole disc golf course, comfortably accommodates up to 14 guests.
Walnut Cellars | Great Views, Fire Pit, Large Yard - Oakland, MD
9.6 5 reviews
Oakland, MD
24/06 – 28/06
272 €/nighttotal: 1088 € (4 )

Walnut Cellars | Great Views, Fire Pit, Large Yard

3 2
apartment , Deer Park
Walnut Cellars, a lakeside property near Oakland, Maryland, offers a four-bedroom dwelling with lake access and proximity to Deep Creek Lake State Park and Wisp Resort.
This 176 square metre (1890 square feet) holiday home sleeps six, boasting three bathrooms, a fully equipped kitchen including dishwasher, smart TVs, and a garden with parking; guests can enjoy jet skiing and fishing nearby.
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