TOP 30 Family friendly vacation rentals in Oakland, Maryland

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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.

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.

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.

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.

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.

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.

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.

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.

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.

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!

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.

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.

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.

Kare Bear Cabin is a cozy lodging establishment located at 158 Glendale Road in Oakland, Maryland, United States. Nestled in a picturesque setting, this charming cabin offers a peaceful retreat for guests looking to unwind and reconnect with nature. The cabin features comfortable accommodations, modern amenities, and a warm, inviting atmosphere. Whether you're seeking a romantic getaway or a family vacation, Kare Bear Cabin provides the perfect setting for a memorable stay in the beautiful Maryland countryside.

Welcome to Owls Nest, your premier destination for real estate and travel services in Oakland, MD. Conveniently located at 240 Penelacre Ln, Owls Nest is dedicated to helping you find your dream home or plan your perfect getaway. As a dual-purpose agency, we specialize in providing comprehensive real estate solutions, whether you're buying, selling, or renting, as well as offering expert travel planning services to ensure your vacations are memorable and stress-free. Our team of experienced professionals is committed to delivering personalized service and expert advice tailored to meet your unique needs. Discover the difference at Owls Nest, where your home and travel dreams take flight.

"Logged and Loaded Cabin" is a charming and rustic retreat nestled in the picturesque surroundings of Oakland, Maryland. Situated at 214 Gallatin Dr, this cozy cabin offers an ideal getaway for those looking to escape the hustle and bustle of everyday life and immerse themselves in the tranquility of nature. The cabin boasts a warm and inviting atmosphere, with carefully curated decor that combines the charm of traditional log cabin aesthetics with modern comforts. Guests can enjoy spacious living areas, comfortable bedrooms, and a fully-equipped kitchen, making it perfect for families, couples, or groups of friends.