TOP 10 Vacation rentals in Oakland, Maryland

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.

OffLake Realty & Rentals is a premier real estate and travel agency located in Oakland, Maryland. Our team of experienced professionals is dedicated to helping clients find the perfect property for their needs, whether it be a permanent residence or a vacation rental. With a prime location on Garrett Highway, we specialize in properties located near the beautiful Deep Creek Lake area. Let us help you find your dream home or vacation rental today!

Bear Paws Vacation Rental is a premier real estate and travel agency located in Oakland, Maryland. Situated at 18025 Garrett Highway, this institution offers a wide range of vacation rental properties for visitors looking to experience the beauty of the area. From cozy cabins to luxurious lakefront homes, Bear Paws Vacation Rental has something for everyone. With top-notch customer service and a commitment to providing unforgettable experiences, this agency is the perfect choice for your next getaway in Maryland. Book your dream vacation today with Bear Paws Vacation Rental.

Raccoon Lagoon Deep Creek Lake Front Vacation Rental is the perfect destination for a relaxing and adventurous getaway in Oakland, Maryland. This lakefront and ski house vacation rental offers 5 bedrooms and 4 bathrooms, with stunning views of Deep Creek Lake from the open floor plan living areas. Guests can enjoy boating, skiing, rafting, hiking, biking, or simply relaxing by the fireplaces or fire pits on the property. Each bedroom and common area is equipped with flat screen smart televisions and expanded cable, perfect for unwinding after a day of outdoor activities. The 8-person hot tub offers a relaxing spot to soak while enjoying views of the lake, and guests can stream music through Bose speakers.

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.

Love and Memories Deep Creek Lake Rental is a charming lodging institution located at 77 Meadow Court in Oakland, Maryland, United States. Situated in the Paradise Ridge Community at Deep Creek Lake, this home offers access to the Community Aquatic Recreation Center (CARC) with a gym and indoor pool for guests to enjoy during their stay. The layout of the home includes a Great Room, Kitchen, Dining Area, Screened-in Porch, Bedrooms with comfortable beds, and a Recreation Room with additional sleeping options. The fenced-in yard is perfect for guests with pets, providing a safe space for furry friends to roam. Guests can relax in the hot tub, gather around the fire pit, or enjoy games like skee ball and foosball. The house offers beautiful views and a peaceful atmosphere, making it a great spot for a relaxing vacation. While some aspects of the home may show signs of wear and tear, the cleanliness and functionality make it a comfortable choice for a getaway. With convenient access to local amenities and activities, Love and Memories Deep Creek Lake Rental is a wonderful place to create lasting memories with loved ones.

Mata's Rental Stays is a leading real estate agency located at 5000 Thayer Center in Oakland, Maryland, United States. We specialize in providing top-quality rental properties for short-term and long-term stays in the area. Our dedicated team of professionals is committed to ensuring a seamless and enjoyable rental experience for our clients. Whether you are looking for a cozy apartment, a spacious house, or a luxurious vacation rental, Mata's Rental Stays has the perfect property to suit your needs. Contact us today to find your ideal rental stay in Oakland, Maryland.

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.

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.

Red Run Cabin 3BR Lake Access is a charming vacation rental located at 156 Red Run Road in Oakland, Maryland. This cozy cabin offers three bedrooms and easy access to the beautiful nearby lake, perfect for a relaxing getaway with family or friends. Whether you're looking to enjoy the great outdoors or simply unwind in a peaceful setting, this property is the ideal choice. Contact our real estate and travel agency to book your stay at Red Run Cabin 3BR Lake Access today.

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.

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.

Timber Rock Village is a premier real estate and travel agency located at 45 Stanton Lane in Oakland, Maryland, United States. Our agency specializes in helping clients find their dream homes in the tranquil setting of Timber Rock Village, nestled in the picturesque mountains of Maryland. Whether you are looking to buy or rent a property, our experienced team is dedicated to providing personalized service to meet your needs. Additionally, we offer travel services to help you explore the beauty of the surrounding area and make the most of your time in this charming location. Contact us today to start your journey towards finding your perfect home or planning your next adventure in Timber Rock Village.

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.

Property Management Services Rent is a reputable real estate agency located at 104 East Oak Street in Oakland, Maryland, United States. We specialize in providing top-notch property management services for both residential and commercial properties. Our team of experienced professionals is dedicated to ensuring that your property is well-maintained and profitable. Whether you are a landlord looking to rent out your property or a tenant in search of a new home or business space, we are here to help. Contact us today to learn more about our services and how we can assist you with all of your property management 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.

Railey Realty is a reputable real estate agency located at 19567 Garrett Highway in Oakland, Maryland. With a strong presence in the local real estate market, Railey Realty is dedicated to helping clients buy, sell, and rent residential and commercial properties. Their team of experienced agents provides personalized service and expert guidance to ensure a smooth and successful real estate transaction. Whether you're looking to purchase your dream home or sell your current property, Railey Realty is committed to helping you achieve your real estate goals. Contact them today to learn more about their services and how they can assist you with all your real estate needs.

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.

April Sound at Deep Creek Lake is a premier real estate and travel agency located in Oakland, Maryland. Situated at 46 Hummingbird Court, this institution specializes in providing luxurious vacation rentals and properties around the stunning Deep Creek Lake area. Whether you are looking for a cozy cabin for a weekend getaway or a spacious lakeside home for a family vacation, April Sound has a wide range of options to suit every need. With their expert knowledge of the area and dedication to customer service, April Sound at Deep Creek Lake is your go-to destination for an unforgettable experience in this beautiful region of the United States.

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.