The Best Holiday home rental in Oakland, Maryland

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.

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.

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.

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.

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!