TOP 30 Best Vacation accommodations in Oakland, Maryland

Deep Creek Vacation Rentals by Vacasa is a premier lodging, real estate, and travel agency located in Oakland, Maryland. Situated at 19509 Garrett Highway, this institution offers a wide range of vacation rental properties in the scenic Deep Creek Lake area. With a focus on providing exceptional customer service and high-quality accommodations, guests can expect a seamless and enjoyable vacation experience. Whether you are looking for a cozy cabin for a romantic getaway or a spacious lakefront home for a family retreat, Deep Creek Vacation Rentals by Vacasa has something for everyone. Book your next vacation with them and create lasting memories in this beautiful destination.

Once in a Blue Moon is a charming lodging institution located at 863 Paradise Heights in Oakland, Maryland, United States. Nestled in a picturesque setting, this cozy retreat offers a unique and unforgettable experience for guests looking to escape the hustle and bustle of everyday life. With comfortable accommodations and personalized service, Once in a Blue Moon is the perfect place to relax and rejuvenate. Whether you're seeking a romantic getaway or a peaceful retreat, this hidden gem is sure to make your stay a memorable one.

Welcome to Deep Creek Vacation Rentals by Vacasa, your premier destination for exceptional vacation rental experiences in the heart of Deep Creek Lake, Maryland. Nestled in the scenic town of Oakland, our agency specializes in offering a diverse range of vacation homes tailored to meet your every need. Whether you're planning a family getaway, a romantic retreat, or an adventure-filled trip, our extensive portfolio of properties ensures that you find the perfect home away from home.

Lazy Bear Lodge at Deep Creek Lake is a charming and cozy retreat located at 173 Bray Run Road in Oakland, Maryland. This institution offers a range of services including lodging, park amenities, real estate services, and travel planning. Nestled in the beautiful surroundings of Deep Creek Lake, guests can enjoy a peaceful and relaxing stay in the heart of nature. The lodge is perfect for those looking to unwind and escape the hustle and bustle of everyday life. Whether you're looking for a weekend getaway, a family vacation, or a romantic retreat, Lazy Bear Lodge has something for everyone. With its convenient location and comfortable accommodations, this institution is the ideal destination for those seeking a tranquil and rejuvenating experience.

Dock Holiday Cottage is a charming and cozy vacation rental located at 1465 Mayhew Inn Road in Oakland, Maryland. Situated in a picturesque setting, this cottage is the perfect destination for those looking to escape the hustle and bustle of everyday life. As a real estate and travel agency, we take pride in providing our guests with top-notch accommodations and exceptional customer service. Whether you're looking for a romantic getaway or a fun-filled family vacation, Dock Holiday Cottage has everything you need to make your stay unforgettable. Book your stay with us today and experience the beauty of Maryland's countryside.

Storch Deep Creek Lake Cabin Rentals is a premier lodging option located in Oakland, Maryland, United States. Situated at 231 Santa Fe Trail, this institution offers a variety of cozy and well-appointed cabins for rent, perfect for a relaxing getaway in the picturesque Deep Creek Lake area. As a real estate agency, Storch Deep Creek Lake Cabin Rentals also provides opportunities for those interested in purchasing a cabin of their own in this beautiful region. Additionally, their services as a travel agency can assist visitors in planning the perfect vacation experience, whether it be a family retreat, romantic escape, or outdoor adventure. With a focus on customer satisfaction and personalized service, Storch Deep Creek Lake Cabin Rentals is the ideal choice for a memorable stay in the heart of nature.

Fox Den Holiday Home is a charming lodging facility located at 137 Paradise Gardens Road in Oakland, Maryland, United States. Nestled in a peaceful and serene setting, this cozy holiday home offers guests a comfortable and relaxing retreat during their stay. The property features well-appointed rooms, modern amenities, and a welcoming atmosphere that makes guests feel right at home. Whether you're looking for a romantic getaway or a family vacation, Fox Den Holiday Home is the perfect destination for your next trip. Experience the beauty of Maryland while enjoying the comforts of this lovely accommodation.

Apple Cottage Holiday Home is a charming lodging located at 560 Glendale Road in Oakland, Maryland, United States. Nestled in a picturesque setting, this cozy cottage offers a peaceful retreat for guests looking to unwind and relax. The cottage features comfortable accommodations, modern amenities, and a welcoming atmosphere. Whether you're looking for a romantic getaway or a family vacation, Apple Cottage Holiday Home is the perfect destination for your next escape. Enjoy the beauty of nature, explore the nearby attractions, and make unforgettable memories at this lovely holiday home.

Gather Inn at Deep Creek Lake Maryland is a premier real estate and travel agency located at 307 Winding Trail Lane in Oakland, Maryland. Specializing in vacation rentals and property management services, Gather Inn offers a wide range of luxurious accommodations and personalized services to make your stay at Deep Creek Lake unforgettable. Whether you are looking for a cozy cabin for a romantic getaway or a spacious lakefront home for a family vacation, Gather Inn has the perfect property for you. With a team of dedicated professionals who are passionate about providing exceptional customer service, Gather Inn is committed to helping you find the perfect home away from home in the beautiful Deep Creek Lake area.

Absolutely Shore is a premier institution located at 1762 Paradise Point Road in Oakland, Maryland, United States. As a unique combination of a lodging facility, real estate agency, and travel agency, Absolutely Shore offers a one-of-a-kind experience for visitors looking to explore the beautiful shores of Maryland. Whether you are in need of a cozy place to stay, looking to buy or rent a property, or seeking assistance with planning your next vacation, Absolutely Shore has got you covered. With a team of dedicated professionals and a commitment to providing top-notch service, Absolutely Shore is the perfect destination for all your lodging, real estate, and travel needs.

Traditions On The Lake is a premier real estate and travel agency located at 20654 Garrett Highway in Oakland, Maryland. Situated along the picturesque shores of a tranquil lake, this institution specializes in providing clients with exceptional properties and vacation rentals in the area. Whether you are looking to buy a lakeside retreat or plan a relaxing getaway, Traditions On The Lake offers personalized service and expertise to help you find the perfect place to call home or escape to. With a focus on quality, comfort, and creating lasting memories, this institution is dedicated to helping clients make their dream of lakeside living a reality.

Some Kind of Wonderful is a charming lodging located at 8 Trailside Way in the picturesque town of Oakland, Maryland. This cozy retreat offers a warm and inviting atmosphere, perfect for travelers looking for a comfortable and relaxing stay. The institution boasts well-appointed rooms, friendly staff, and a convenient location near local attractions and outdoor activities. Whether you're visiting for a weekend getaway or an extended stay, Some Kind of Wonderful is the ideal choice for your accommodations in Oakland.

Bella Vista is a charming lodging institution located at 20254 Garrett Highway in Oakland, Maryland, United States. Nestled in the picturesque surroundings of the area, Bella Vista offers a serene and peaceful retreat for guests looking to escape the hustle and bustle of everyday life. The institution boasts comfortable accommodations, friendly staff, and a range of amenities to ensure a pleasant stay for all visitors. Whether you are looking for a romantic getaway, a family vacation, or a solo retreat, Bella Vista is the perfect destination for your next trip.

Serenity Ridge is a tranquil lodging institution located at 180 Roman Ridge Road in Oakland, Maryland, United States. Nestled in the heart of nature, this serene retreat offers a peaceful and rejuvenating escape for guests seeking relaxation and tranquility. With comfortable accommodations, breathtaking views, and a variety of amenities, Serenity Ridge is the perfect destination for a peaceful getaway. Whether you're looking to unwind in nature, explore the nearby attractions, or simply relax and recharge, Serenity Ridge provides a serene and welcoming environment for all.

The Suites at Silver Tree is a luxurious lodging institution located at 565 Glendale Road in Oakland, Maryland, United States. Nestled in the picturesque surroundings of Deep Creek Lake, this resort offers a serene retreat for guests looking to relax and unwind. The spacious suites are elegantly appointed with modern amenities and feature stunning views of the lake and surrounding mountains. Guests can enjoy a range of on-site facilities including a fitness center, indoor pool, hot tub, and a cozy fireplace lounge. Whether you're seeking a romantic getaway or a family vacation, the Suites at Silver Tree provides the perfect setting for a memorable stay.

Bears Lair is a cozy lodging institution located at 94 Lehman Lane in Oakland, Maryland, United States. Nestled in the heart of nature, this charming retreat offers a peaceful and relaxing atmosphere for guests to unwind and recharge. With comfortable accommodations and friendly staff, Bears Lair is the perfect destination for those seeking a tranquil getaway in the beautiful surroundings of Maryland. Whether you're looking to explore the nearby attractions or simply relax in the comfort of your room, Bears Lair has everything you need for a memorable stay.

Mountaintop Condos is a premier real estate and travel agency located at 66 Meadow Court in Oakland, Maryland, United States. As a member of the Pocahontas County Chamber of Commerce, we are committed to providing exceptional service and accommodations for our clients. With dynamic pricing on all channels including Booking.com, Expedia, Airbnb, and more, we ensure that our clients receive the best deals and options for their stay. Whether you are looking for a cozy mountain retreat or a luxurious condo with breathtaking views, Mountaintop Condos has something for everyone. Book your next vacation with us and experience the beauty of the mountains in style and comfort.

Mountain Escape at Yough Mtn Resort is a premier real estate and travel agency located in the picturesque town of Oakland, Maryland, United States. Situated at 327 Birchwood Drive, our institution offers a range of luxurious mountain escape properties within the stunning Yough Mountain Resort. Whether you are looking for a cozy cabin for a weekend getaway or a spacious vacation home for your family, our experienced team is dedicated to helping you find the perfect escape in this tranquil mountain setting. With unparalleled customer service and a deep knowledge of the local area, Mountain Escape at Yough Mtn Resort is your go-to destination for a memorable and relaxing retreat.

The Barn on Lake Shore is a charming institution located at 562 Lake Shore Drive in Oakland, Maryland, United States. This unique establishment offers a combination of lodging, real estate, and travel services. Nestled by the picturesque Lake Shore, guests can enjoy a peaceful and serene atmosphere while staying in cozy accommodations. Whether you are looking for a relaxing getaway, interested in purchasing real estate in the area, or planning your next travel adventure, The Barn on Lake Shore has something to offer for everyone. Experience the beauty of Oakland, Maryland at this one-of-a-kind institution.

Deep Creek Paradise is a stunning lake-front home located at 1738 Paradise Point Road in Oakland, Maryland. This dreamy retreat is perfect for nature lovers, offering beautiful wooded areas, a private dock, and plenty of spots for sunbathing right outside your door. From swimming and boating on the lake to relaxing on the raised deck with a cup of coffee, this property has everything you need for a peaceful getaway. Inside, you'll find cozy amenities like fireplaces, a jetted bathtub, and multiple TVs, as well as a pool table for entertainment. With private lake access and a dock slip, you can enjoy all that Deep Creek Lake has to offer. Plus, guests have free access to the Community Aquatic Recreation Center for fitness and wellness activities. Whether you're planning a summer vacation, holiday celebration, or weekend escape, Paradise at Deep Creek is the perfect destination. Book your stay today and experience true paradise in Maryland!

Herrington Manor State Park is a picturesque park located at 222 Herrington Lane in Oakland, Maryland, United States. This popular tourist attraction offers visitors a peaceful retreat surrounded by lush forests, serene lakes, and scenic hiking trails. Outdoor enthusiasts can enjoy activities such as camping, fishing, boating, and picnicking in this beautiful natural setting. The park also features cozy cabins for overnight stays and is the perfect destination for a relaxing weekend getaway or outdoor adventure. With its tranquil atmosphere and stunning landscapes, Herrington Manor State Park is a must-visit destination for nature lovers and outdoor enthusiasts alike.

Will O' the Wisp Condominiums is a charming lodging option located at 20160 Garrett Highway in Oakland, Maryland, United States. Nestled in the heart of nature, this institution offers cozy and comfortable condominium units for guests to enjoy a relaxing getaway. With picturesque views of the surrounding landscape, guests can unwind and rejuvenate in this serene setting. Whether you are looking for a romantic escape or a family vacation, Will O' the Wisp Condominiums provides a peaceful retreat for all.

Shiver Me Timbers is a charming store located at 80 Whitetail Court in Oakland, Maryland, United States. This true oasis in a cabin shell offers accommodation for twelve guests in four bedrooms. The open layout of the home allows for group activities such as cooking, dining, and entertaining in the lofty great room. The warm glow of rich wood gives the cabin a feeling of rustic splendor. Guests can enjoy the bonus room with a hot tub, fireplace, television, and conversation set, perfect for entertaining. The home provides 2 seasonal state park passes for access to nearby state parks. Located in the Yellowstone Community at Deep Creek Lake, this home features a main level with a kitchen, living area, dining area, and two bedroom suites. The upper level has a loft and another bedroom suite, while the lower level includes a den/game area, wet bar, and bedroom. Guests have praised the cozy and welcoming atmosphere of the house, as well as its proximity to outdoor activities and amenities. Overall, Shiver Me Timbers is a perfect retreat for families and groups looking to relax and enjoy the beauty of Deep Creek Lake.

El Canelo Motel is a cozy lodging option located at 12678 Garrett Highway in Oakland, Maryland, United States. This charming motel offers comfortable and affordable accommodations for travelers looking to explore the scenic beauty of the area. With easy access to nearby attractions and outdoor activities, El Canelo Motel is the perfect choice for those seeking a relaxing getaway. The friendly staff and convenient location make this motel a top choice for visitors to the Oakland area.

Wild Yough Glamping Huts offers a unique and luxurious camping experience in the scenic mountains of Garrett County, Maryland. Located on the banks of the Youghiogheny River, our huts provide a comfortable and stylish way to enjoy the great outdoors without sacrificing modern amenities. Our owners, who have traveled extensively and stayed in glampgrounds around the world, have brought their expertise to create a one-of-a-kind experience in the Appalachian wilderness. Conveniently located near public lands, lakes, and rivers, Wild Yough is the perfect base for outdoor adventures. Whether you're hiking, fishing, or simply relaxing by the campfire, our huts provide a cozy retreat at the end of the day. With options for pets and additional amenities like A-Frames and firewood, booking your stay is simple and hassle-free.

Oak - Mar Motel is a charming lodging establishment located at 208 North 3rd Street in Oakland, Maryland, United States. This cozy motel offers comfortable accommodations for travelers looking to explore the beautiful surroundings of Oakland. With its convenient location, guests can easily access nearby attractions and activities. The Oak - Mar Motel provides a warm and welcoming atmosphere, making it the perfect place to relax and unwind after a day of adventure. Whether you are visiting for business or pleasure, this motel is the ideal choice for your stay in Oakland.

Riverside Suites is a charming lodging establishment located at 1503 Maryland Highway in Oakland, Maryland, United States. Nestled along the picturesque riverside, this cozy retreat offers comfortable accommodations and stunning views of the surrounding natural beauty. Guests can enjoy a peaceful and relaxing stay in well-appointed suites, complete with modern amenities and thoughtful touches. Whether you're seeking a romantic getaway or a family vacation, Riverside Suites provides a tranquil setting for your next escape. Experience the beauty of Maryland's countryside while staying at Riverside Suites.

Welcome to the Quaint Inn & Suites, a charming lodging option located at 2704 Deep Creek Drive in McHenry, Maryland, United States. Our cozy inn is the perfect retreat for those looking to explore the nearby Wisp Ski Resort, just two miles away. Offering budget-friendly accommodations, we provide a warm and inviting atmosphere for your next ski getaway. Situated just a mile from the popular tourist destination Deep Creek Lake, our location is ideal for those seeking outdoor adventures. The Adventure Sports Center International, known for their whitewater rafting courses, is also close by. Explore the beauty of Garrett County, with its 90,000 acres of scenic state land featuring lakes, waterfalls, mountains, and farms. Don't miss the opportunity to visit the Deep Creek Lake Discovery Center, just minutes away.

The Inn at Deep Creek is a charming lodging establishment located at 19638 Garrett Highway in Oakland, Maryland. Nestled in the heart of the beautiful Deep Creek Lake area, this inn offers cozy accommodations and warm hospitality for guests looking to relax and unwind in a serene setting. With comfortable rooms, modern amenities, and a convenient location near outdoor activities and attractions, the Inn at Deep Creek is the perfect destination for a peaceful getaway in the United States.

Serenity Summit is a peaceful retreat nestled in the heart of Oakland, Maryland. Located at 308 Winding Trail Lane, this tranquil lodging institution offers a serene and rejuvenating escape from the hustle and bustle of everyday life. Surrounded by the beauty of nature, guests can unwind and relax in the comfortable accommodations while taking in the breathtaking views of the surrounding landscape. Whether you are looking for a romantic getaway, a family vacation, or a solo retreat, Serenity Summit provides a tranquil setting for all. Immerse yourself in the serenity of the mountains and experience a truly peaceful stay at this charming institution.