TOP 10 Best Luxury vacation packages 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.

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.

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.

Western Trails is a premier travel agency located at 4009 Mayhew Inn Road in Oakland, Maryland, United States. With a focus on providing exceptional travel experiences, Western Trails offers a wide range of services to help clients plan their dream vacations. Whether you're looking to explore the great outdoors, relax on a tropical beach, or immerse yourself in a new culture, Western Trails has the expertise and resources to make your travel dreams a reality. Contact us today to start planning your next adventure!

Wisp Away Cabin is a charming real estate and travel agency located at 83 Boston Post Road in Oakland, Maryland, United States. Specializing in vacation rentals and property sales in the picturesque Wisp Resort area, Wisp Away Cabin offers a wide range of cozy cabins and luxurious homes for visitors looking to escape and unwind in the beautiful mountains of Maryland. With a dedicated team of professionals, Wisp Away Cabin ensures a seamless and unforgettable experience for all clients, whether they are looking to rent a vacation property or purchase their dream mountain home. Plan your next getaway with Wisp Away Cabin and let the magic of the mountains whisk you away.

Lure of the Lake is a charming institution located at 410 South Blakeslee Road in Oakland, Maryland, United States. As a unique blend of lodging, real estate agency, and travel agency, Lure of the Lake offers a one-of-a-kind experience for visitors looking to explore the stunning beauty of Deep Creek Lake and its surrounding areas. Whether you are seeking a cozy cabin rental, interested in purchasing a lakefront property, or in need of expert guidance for planning your next adventure, Lure of the Lake has you covered. With a team of knowledgeable professionals and a passion for all things lake-related, Lure of the Lake is your gateway to an unforgettable experience in this picturesque region.

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.

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 A206, a cozy 1 bedroom suite located at 565 Glendale Road in Oakland, Maryland, United States. This charming lodging option offers a standard view, a comforting fireplace, and a private balcony where you can step outside for some fresh air and enjoy the scenic surroundings. Perfect for a romantic getaway or a relaxing solo retreat, A206 provides all the amenities you need for a comfortable stay. Book your stay now and experience the tranquility of this beautiful location.

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.

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.

Pleasant Valley Dream Rides is a premier travel agency located at 1689 Pleasant Valley Road in Oakland, Maryland, United States. Our agency specializes in creating unforgettable travel experiences for our clients, offering a wide range of exciting and unique adventures. From luxury cruises to exotic getaways, we are dedicated to making your travel dreams a reality. Let us help you plan your next unforgettable journey and create memories that will last a lifetime.

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.

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.

Little Branch Lodge is a charming real estate and travel agency located at 153 Roman Ridge Road in Oakland, Maryland, United States. Our friendly and knowledgeable staff are dedicated to helping clients find the perfect property or plan the ultimate vacation getaway. Whether you're looking to buy a new home, rent a cozy cabin in the mountains, or book a dream vacation, Little Branch Lodge is here to make your real estate and travel dreams a reality. With a personalized approach and attention to detail, we strive to provide exceptional service and create unforgettable experiences for our clients. Visit us today and let us help you find your little piece of paradise.

Almost Heaven 5BR Lakefront is a premier real estate and travel agency located at 2150 Stockslager Road in Oakland, Maryland, United States. Offering luxurious lakefront properties with five bedrooms, this institution provides a truly heavenly experience for those looking to escape the hustle and bustle of everyday life. Whether you are seeking a peaceful retreat or a fun-filled vacation, Almost Heaven 5BR Lakefront has the perfect property for you. With stunning views, top-notch amenities, and exceptional customer service, this institution is dedicated to making your stay unforgettable. Book your dream getaway with Almost Heaven 5BR Lakefront today and experience a slice of paradise in Maryland.

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!

180 Degrees is a premier real estate and travel agency located at 121 Timberloft Lane in Oakland, Maryland, United States. With a team of experienced professionals, we offer top-notch services in buying, selling, and renting properties, as well as planning unforgettable vacations and travel experiences. Our mission is to provide our clients with 180 degrees of exceptional service, ensuring their real estate and travel needs are met with efficiency and expertise. Visit us today and let us help you turn your dreams into reality.