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Best Vacation rentals and Airbnb offers in Oakland, MD
9.0 2 reviews
Oakland, MD
08/09 – 08/11
$322/nightTotal: $644 (2 )
B204 One Bedroom Lake View
1 2
apartment , Deer Park
The B204 - 1 Bedroom Lake View Suite at Lakefront Hotel is located in Oakland, a district in Deer Park, offering stunning lake views and a convenient distance from Morgantown Municipal Airport (45 miles away). The hotel has received excellent ratings for user experience, location, and cleanliness. This suite has one bedroom and one bathroom, and can accommodate up to four guests. Guests can enjoy amenities such as a private balcony with lake views, a fully equipped kitchenette, free Wi-Fi, free private parking, a 24-hour front desk, cable TV, and comfortable amenities.
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.
9.8 73 reviews
Oakland, MD
07/10 – 07/12
$217/nightTotal: $434 (2 )
Quiet 2 Bdrm Cottage W/firepit & Trees
1 2
cabin , Deer Park
This cozy cabin is located just minutes from a state park, Wisp Resort, and the town of Oakland, offering easy access to outdoor activities and attractions. The surrounding area is peaceful and wooded, providing a tranquil retreat from the hustle and bustle. The cabin features two bedrooms and one bathroom, comfortably accommodating up to five guests. Amenities include a fully equipped kitchen, a private fire pit, a hammock, a large deck with a gas fireplace, and a wood stove for cozy evenings.
Oakland, MD
08/09 – 08/11
$239/nightTotal: $478 (2 )
Enjoyable 2-bedroom Apartment In Lovely Oakland Near Local Hotspots
2 2
apartment , Oakland
This 2-bedroom apartment in Oakland provides direct access to Deep Creek Lake and Deep Creek Lake State Park, and is less than 2 miles from Wisp Resort, the Baltimore and Ohio Railroad Station, and Funland. This residence offers internet, a kitchen with a fridge and microwave, heating, an iron, and accommodates up to 3 guests with a queen bed and a twin bed, with a 11:00 AM check-out.
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.
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.
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.
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.
9.3 31 reviews
Oakland, MD
08/09 – 08/11
$250/nightTotal: $500 (2 )
A311 One Bedroom & Loft Lake View
1 2
apartment , Deer Park
This Deer Park hotel, located about 45 miles from Morgantown Municipal Airport, offers a convenient and comfortable stay for travelers. Guests consistently praise the hotel's excellent cleanliness and location. The A114 - 1 Bedroom Suite with Standard View, Private Bedroom, & Fireplace! features a separate bedroom for privacy and a fully equipped kitchenette for convenience. Guests can enjoy a range of amenities, including a private balcony, free parking, free Wi-Fi, a fireplace, a sauna, a spa, a fitness center, and a garden.
10 80 reviews
Oakland, MD
07/10 – 07/12
$197/nightTotal: $394 (2 )
Lil' Sumpin
1 2
cabin , Oakland
This renovated travel trailer, near Oakland, Maryland, sits half a mile off the road, providing easy access to Herrington Manor and Swallow Falls State Parks and Deep Creek Lake. The 1-bedroom, 1-bathroom tiny house sleeps two, features a fully equipped kitchenette with a cooktop, microwave, and coffee maker, a deck overlooking a creek, and a shared fireplace; nearby outdoor activities include hiking, biking, and boating.
9.9 196 reviews
Oakland, MD
07/10 – 07/12
$177/nightTotal: $354 (2 )
The Original Hob
1 2
cabin , Oakland
This charming cabin rental is located in Garrett County, near Oakland, within 5 miles of State Parks and Deep Creek Lake, offering a peaceful escape from city life. The property consistently receives excellent ratings for its cleanliness, location, and overall user experience. The property features two small cabins, each with unique features, perfect for a romantic getaway or a small family trip. Guests can enjoy a shared kitchen and bathroom, and the property boasts a hammock, swings, an outdoor shower, an outdoor fireplace, and water chairs for relaxing by the creek.
8.9 15 reviews
Oakland, MD
08/09 – 08/11
$419/nightTotal: $838 (2 )
206a Efficiency One Bath
1 2
house , Deer Park
This Deer Park house is located in Oakland, just 45 miles from Morgantown Municipal Airport. The property has received excellent ratings for location, cleanliness, and user experience. This one-bedroom vacation rental features a separate seating area and a fully equipped kitchenette with a microwave and fridge. Enjoy the outdoor space with a terrace and balcony, relax by the fireplace, and take advantage of amenities like a swimming pool, jacuzzi, sauna, and fitness center.
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.
10 1 review
Oakland, MD
07/10 – 07/12
$834/nightTotal: $1668 (2 )
278 M² House ∙ 5 Bedrooms ∙ 12 Guests
5 2
house , Oakland
This spacious 5-bedroom vacation rental is located in the Deep Creek Lake area, offering convenient access to hiking trails, ski slopes, boating, and restaurants. This pet-friendly house spans 2990 square feet with a three-level layout, featuring a game space with a pool table and foosball, comfortably accommodating up to 12 guests with amenities like a hot tub and firepit.
10 3 reviews
Oakland, MD
08/09 – 08/11
$415/nightTotal: $830 (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.
8.2 18 reviews
Oakland, MD
08/09 – 08/11
$418/nightTotal: $836 (2 )
183 M² House ∙ 4 Bedrooms ∙ 10 Guests
3 2
house , Oakland
Wooded Bliss, a spacious Oakland house rental near Deep Creek Lake, is located less than four miles from Swallow Falls State Park and a fifteen-minute drive from Wisp Resort. This 1960-square-foot home features three bedrooms, two bathrooms, sleeps ten guests, and includes a fully equipped kitchen, private boat slip, stone fireplace, outdoor deck with fire pit, and proximity to local restaurants and shops.
9.8 267 reviews
Oakland, MD
08/09 – 08/11
$498/nightTotal: $996 (2 )
Charming, Eco-friendly Cabin Retreat, Heart Of Deep Creek
3 2
cabin , Oakland
This family-friendly cabin is located just 1.1 miles from Deep Creek Lake and within 6 miles of attractions like Funland, Deep Creek Lake State Park, Wisp Resort, and Lodestone Golf Club, offering easy access to a variety of activities. Guests consistently rate this vacation rental excellent, making it a popular choice for families and groups. The cabin features 3 bedrooms and 2 bathrooms, comfortably accommodating up to 9 guests. Amenities include a fully equipped kitchen, a game room, a fireplace, a spa tub, a terrace, and a garden, perfect for a relaxing getaway.
Best Oakland, MD vacation rentals with parking
8.6 71 reviews
Oakland, MD
08/09 – 08/11
$473/nightTotal: $946 (2 )
Home Sweet Cabin
5 2
cabin , Oakland
Home Sweet Cabin is located in Oakland, Maryland, a short drive from Deep Creek Lake and about 47 miles from Morgantown Municipal Airport. The cabin has consistently received high ratings for its cleanliness, location, and overall experience. This 4-bedroom vacation home offers 1400 square feet of space. The cabin comes equipped with a fully equipped kitchen, a patio, free Wi-Fi, and free private parking, as well as access to nearby skiing and cycling opportunities.
10 5 reviews
Oakland, MD
07/10 – 07/12
$333/nightTotal: $666 (2 )
A206 One Bedroom Standard View
1 2
apartment , Deer Park
The A206 One Bedroom Standard View suite is located in Oakland, a short drive from Deer Park and about 45 miles from Morgantown Municipal Airport. This apartment receives excellent ratings for location, cleanliness, and overall user experience. The suite offers 480 square feet of space, accommodating up to four guests in one bedroom and one bathroom. Enjoy amenities like a private balcony, fireplace, free parking, a fully equipped kitchenette, air conditioning, a fitness center, and a sauna.
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.
8.6 5 reviews
Oakland, MD
08/09 – 08/11
$434/nightTotal: $868 (2 )
139 M² House ∙ 4 Bedrooms ∙ 10 Guests
4 2
house , Oakland
This Oakland house rental, near Deep Creek Lake State Park, offers easy access to outdoor recreation including swimming, hiking, and skiing within a 5–10 minute drive. This 1490-square-foot vacation home boasts four bedrooms, three bathrooms, and accommodates up to ten guests, featuring a fully equipped kitchen, hot tub, swimming pool, and multiple decks.
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.
9.6 16 reviews
Oakland, MD
08/09 – 08/11
$427/nightTotal: $854 (2 )
Will O' The Wisp: 206a Efficiency/one Bath
1 2
apartment , Deer Park
This Deer Park apartment is located just a short walk from Deep Creek Lake, offering easy access to scenic views, water activities, and nearby attractions like Deep Creek Lake State Park and Funland. Guests consistently rate this rental as excellent. This one-bedroom, one-bathroom apartment comfortably sleeps three guests. Amenities include a fully equipped kitchen, a terrace, a swimming pool, a jacuzzi, a sauna, a spa, a fitness center, and a concierge service.
10 7 reviews
Oakland, MD
08/09 – 08/11
$197/nightTotal: $394 (2 )
Couples Retreat: The Hayloft- Rustic Escape For 2
1 2
farm , Crellin
This renovated barn apartment near Oakland, Maryland offers a unique glamping experience on a 26-acre farm, providing easy access to Deep Creek Lake and Garrett County's hiking trails. This 500-square-foot rental features one bedroom, one bathroom, and accommodates two guests, complete with a kitchen (fridge, microwave), air conditioning, a terrace, parking, and excellent guest reviews; enjoy on-site vegetable picking and scenic sunset views from a private deck.
9.0 49 reviews
Oakland, MD
07/10 – 07/12
$958/nightTotal: $1916 (2 )
Trail's End - Dog-friendly 5br W/ Hot Tub, Pool Table Near Wisp
5 2
apartment , Accident
This lakefront home in Accident, Maryland, is less than a mile from Funland, Deep Creek Lake, and Wisp Resort, and 2.5 miles from the Garrett County Dog Park. This 2,520-square-foot vacation rental boasts five bedrooms, four bathrooms, sleeps ten guests, and features a Jacuzzi, terrace, and fully equipped kitchen with a dishwasher, plus free Wi-Fi and a fireplace.
8.6 9 reviews
Oakland, MD
08/09 – 08/11
$631/nightTotal: $1262 (2 )
218 M² House ∙ 4 Bedrooms ∙ 12 Guests
4 2
house , Oakland
Lucky 12, a spacious house in Oakland's Mountainside Community, is minutes from Deep Creek Lake State Park and Wisp Resort. This 2,340-square-foot vacation rental boasts four bedrooms, three bathrooms, sleeps twelve, and features a pool, hot tub, tennis court, and multiple entertainment options including billiards and karaoke.
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.
Oakland, MD
08/09 – 08/11
$432/nightTotal: $864 (2 )
Charming 4br Home - Hot Tub - Oakland
4 2
house , Oakland
This vacation rental is located in Oakland, 37 miles from Morgantown Municipal Airport. This 2460 square foot house offers four bedrooms, three bathrooms, and a guest capacity of 19, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, a hot tub, and a fireplace.
This McHenry, Maryland cabin is located near Deep Creek Lake and Deep Creek Lake State Park, offering easy access to Wisp Resort. This pet-friendly 580-square-foot duplex suite features a king bed, jetted tub, gas fireplace, 55" smart TV, kitchenette, and accommodates two guests, with a connecting door option for groups.
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.
9.0 14 reviews
Oakland, MD
08/09 – 08/11
$266/nightTotal: $532 (2 )
Historic Alpine Lakeside Manor
4 2
cabin , Terra Alta
Alpine Lakeside Manor, a historic 1920s hunting lodge on Alpine Lake in Terra Alta, offers a unique lakefront location closer than other properties due to its pre-zoning construction, near Deep Creek Lake and Cranesville Swamp. This 19,380-square-foot retreat boasts three bedrooms, three bathrooms, and sleeps nine, featuring a master suite with a whirlpool tub, access to resort amenities (including a heated indoor pool and fitness center), and proximity to Swallow Falls State Park and Hovatter's Zoo.