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Vacation rentals in Oakwood

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Top-rated vacation rentals in Oakwood

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A single-story cottage is surrounded by lush greenery and vibrant flower beds. A wooden deck extends around the front, providing access to the home. The well-maintained lawn features a variety of plants and shrubs, enhancing the inviting outdoor space.
Cottage in North East
4.98 out of 5 average rating, 701 reviews

Persimmon Pastures

A quiet country setting in North East MD..located on a 7 acre horse farm with easy access to I95. Enjoy all the serenity of the country yet close to the shopping, marinas, and within 50 mile access to Baltimore, Wilmington and Philadelphia. The property is also within 30 minutes of Fair Hill Natural Resources Area with 5,500+acres and 80+ miles of trails for hiking, biking, and beautiful scenery. Pets are allowed. A pet (dog/cat) fee of $5/night/pet will be requested the day of your arrival.

Top guest favorite
An A-frame cabin is surrounded by lush greenery, featuring large glass windows that reflect the surrounding trees. A wooden deck extends from the cabin, complemented by a wooden fence that provides privacy. A gravel pathway leads to the entrance, enhancing the outdoor setting.
Cabin in Narvon
4.98 out of 5 average rating, 234 reviews

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.

Top guest favorite
A historic stone exterior is showcased, featuring a dark green door adorned with a circular wreath. Two rectangular windows with individual panes complement the textured stone walls. Planters with greenery are seen beneath the windows, adding a touch of nature to the entrance.
Home in Pequea
4.97 out of 5 average rating, 117 reviews

1700’s historic waterfront cottage

Be a part of history while staying on this waterfront property of the Ironmaster's Mansion. The two-story stone guesthouse, steps away from the mansion, was built in the year 1715. The timeless character of the home, paired with the peaceful property creates an escape that feels like you've gone back in time, all while being only 20 minutes outside of Lancaster City. The mansion was home to the first treasurer of the US, General Edward Hand’s daughter, and President Buchanan’s fiance.

Top guest favorite
The exterior view of the log cabin is set amidst a lush, wooded landscape. A stone path leads to the cabin, which features a spacious outdoor deck adorned with plants and seating. The serene ambiance of the surrounding nature invites relaxation.
Place to stay in Airville
4.98 out of 5 average rating, 281 reviews

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.

Top guest favorite
A welcoming seating area features two comfortable recliners and a cozy couch, adorned with decorative pillows. A wooden table is positioned nearby, and a bright flower arrangement adds a lively touch to the space. Light enters through framed windows dressed with elegant curtains.
Apartment in Peach Bottom
4.98 out of 5 average rating, 123 reviews

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!

Top guest favorite
A wooden deck is presented with two rocking chairs, positioned on a textured area rug. Surrounding trees offer a lush backdrop, enhancing the natural setting. The rustic log construction of the cabin complements the peaceful ambiance of the outdoor space.
Cabin in Cecil County
5 out of 5 average rating, 128 reviews

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.

Top guest favorite
A two-story brick home is set on a grassy lawn surrounded by trees. Large windows allow natural light to fill the front rooms, while a welcoming front door is framed by a small porch. The peaceful rural setting enhances the house's charm.
Home in Darlington
4.96 out of 5 average rating, 100 reviews

Country Cape Cod, The Peddler House

Come stay in a country Cape Cod close to wildlife and water. Nearby Peddler Run flows into the lake above the Conowingo Dam. It's just a short walk down a country road where fishing, boating, birding, kayaking, hiking and photography abound. This area is a respite for nature lovers and a popular nesting place for eagles and osprey. The Susquehanna State Park and Mason Dixon trails are close by. This lovingly restored home features elements of retro charm found throughout.

Top guest favorite
A spacious room features a king-sized bed framed by framed photographs. A wooden chair sits beside a small table with a plant. Sliding glass doors open to a private balcony, allowing natural light to fill the space.
Guest suite in Peach Bottom
5 out of 5 average rating, 212 reviews

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.

Top guest favorite
Cottage in Charlestown
4.96 out of 5 average rating, 291 reviews

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

Top guest favorite
Home in Whiteford
4.96 out of 5 average rating, 105 reviews

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.

Top guest favorite
A rustic gazebo is illuminated softly at night, showcasing a cozy sleeping area with a Queen bed dressed in warm linens. A wooden cafe table and chairs are positioned beside the bed, while decorative lanterns and fairy lights create a welcoming ambiance throughout.
Place to stay in Havre de Grace
4.93 out of 5 average rating, 160 reviews

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.

Top guest favorite
A fox stands in a grassy meadow, with a historic building located nearby. The background reveals a tranquil lake and distant hills, under a softly lit sky.
Guest suite in Darlington
4.98 out of 5 average rating, 319 reviews

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.

Popular amenities for Oakwood vacation rentals