Vacation rentals in Oakwood

The Roundtop Chalet (romantic couples retreat)

Indulge in a getaway to our charming cabin, the perfect retreat for all your special celebrations - be it anniversaries, birthdays, or simply a much-needed escape from routine. Perfectly designed for romantic getaways, this cabin seamlessly blends rustic charm with modern comforts. Savour the warmth of a cozy fireplace, unwinding in a hot tub,and indulge with unlimited lattes, crafted by our Breville Touch Espresso Machine. Embrace serenity at its finest and make memories that will last forever

Hillside Haven |Hot Tub & Sauna

Kick back & relax in this newly built A-frame cabin with an outdoor space featuring a large deck overlooking the hillside. Enjoy the custom made cedarwood sauna, hot tub, firepit with hanging egg chairs while listening to the beautiful waterfall feature. Inside, there is a fully stocked kitchen including nespresso machine, air fryer, blender and more. King size bed with a Helix Hospitality mattress dressed with luxe Brooklinen linens & pillows. Spacious bathroom with a large stand up shower.

Tranquil Carriage House*MCM *Country *Wildlife

The Aberdeen Carriage House is in a country setting with a country road. We are near city limits and have most of your needs right here. You have a grocery store, dollar store, Target, Walgreens, Planet Fitness, and restaurants in five minutes. Historic Havre de Grace, Ripken Stadium, Vineyards, Boating, and Golfing, only ten minutes. Baltimore and Stadiums are only 35 minutes down I95. The house is spotless and fully loaded with all the comforts of home—pet and chemical-free space.

Waterfront Log Cabin with Hot Tub

Situated on the water's edge of Muddy Creek, this newly renovated log cabin offers a unique, luxury getaway for those seeking a stay immersed in all that nature has to offer. While relaxing on the spacious outdoor deck, you will be treated with a panoramic view of Muddy Creek complete with an occasional sighting of the neighborhood eagle. Perfectly set up for a romantic getaway for two, The Log Cabin on Muddy Creek was created to provide a space for couples to rest and reconnect.

Peaceful Paradise

Welcome to beautiful, southern Lancaster County! Our guest suite is a perfect spot for a relaxing get-away. If you are looking for a peaceful place to unwind and enjoy lovely country views or just looking for a nice place to rest after a long day of sightseeing and hiking- you have come to the right place. Take breath-taking back roads through Amish country to historic Strasburg or Lancaster city. Great shopping, golfing, and parks are nearby. We look forward to hosting you!

Waterfront cabin home - 9+ private wooded acres

Gunpowder Cabin is a peaceful getaway set on 9+ wooded acres and a private drive in Northern Maryland, just an hour from Baltimore. With a half mile of hiking trails, and over 600 feet of frontage on Octoraro Creek, there are numerous options for taking in the natural beauty: warm up by our two firepits, lounge in a hammock, take a dip in the river, or fish for trout from the shoreline. A secluded retreat that feels remote, but moments from the civilization you came to escape.

Conowingo Creek Casual

Kick back and relax in this handicap accessible, clean and stylish country charm efficiency apartment, complete with two outdoor seating spaces, walking paths and beautiful scenery located in rural southern Lancaster County. The area is surrounded by country and Amish charm with nearby hiking trails, while a 30 minute drive will have you in downtown historic Lancaster City where you can stroll, shop and on Tuesday, Friday and Saturday visit the historic Central Market.

Waterfront Retreat w/ Hot Tub, Games & Views

Escape to River Haven, a 7,000+ sq. ft. waterfront retreat on the Susquehanna River, perfect for groups of up to 20. Relax in the hot tub, play pickleball, pool, ping-pong, and air hockey, or unwind on expansive decks with scenic views. The home features a fully equipped kitchen, spacious bedrooms, 4.5 baths, and family-friendly amenities. With a kayak launch nearby, trailer parking, and a whole-house generator, River Haven is made for memorable getaways.

Delightful 12x16 Glamping Gazebo/Tent

Rustic/Glamping Gazebo/Tent situated privately on our property (backyard) of 1.5 acres in a residential neighborhood. As it says Rustic and “Glamping”..meaning an upgraded camping experience, but by no means can we offer the same comfort temperature wise as an indoor setting. A fun stop for the night, or enjoy a full evening with a movie and firepit. Also, there are plenty of restaurants to choose from in the area, as well several local breweries.

South Acres

Unplugged retreat. Great for birders, piano players, gardening fans, antiquers. Twenty minutes from historic Havre de Grace. Nearby gardens include: Longwood Gardens; Chanticleer Garden; Winterthur Museum, Garden, and Library; and LaDew Topiary Gardens. Small kitchen with microwave, sink, fridge, and coffee maker. Private entrance. Smoke detectors, hair dryer. No WiFi. No stove.

Brick Hill farm guesthouse

Come stay on the farm where we aim to create an atmosphere of relaxation. It’s an opportunity to get away from the hustle and bustle of life. Start your day with a fresh cup of coffee or tea and enjoy the scenery from the rocking chairs on the porch. End the day gathering around the campfire if you wish. Whether you like the outdoors or not we hope you van rest & relax!

The River Cottage

Take it easy in this unique cottage built in the 1800s nestled upon the Granite Cliffs of Port Deposit Maryland. While enjoying your tranquil get away you’re minutes from local shops, local dining, local wineries, local breweries and a local marina. There is plenty of sightseeing and wildlife. If you enjoy fishing and kayaking it’s just a short distance away.