
Holiday houses in Oakwood
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Top-rated holiday rentals in Oakwood
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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
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Charming 3 bedroom home nestled in the woods
This charming home is just the place you are looking for with beautiful peaceful settings both inside and out. Relax in the spacious family room (sleeper sofa) next to the open kitchen stocked with all your needs! You will get a good night sleep in either the master bedroom with attached bathroom, or a second bedroom which is right next to a large bathroom with a tub that can also be shared with the third bedroom with 2 twin beds Enjoy your morning coffee on the porch in this peaceful wooded lot
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Quiet Cottage w/ Fresh Eggs near Sight & Sound
Escape to a quiet country cottage where mornings begin with fresh eggs from the chicken coop and evenings end around the fire pit beneath the stars. Updated with a modern farmhouse style, The Blue Cottage offers a peaceful retreat just minutes from Sight & Sound Theatre, Strasburg Railroad, Cherry Crest Adventure Farm, and many of Lancaster County's most popular attractions. Whether you're here to explore Amish Country or just unwind, our cottage is the perfect place to relax and reconnect.
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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.
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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.
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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!
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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.
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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.
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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.
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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.
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2 Bedroom winery retreat.
This 2 bedroom country house retreat shares its location with a beautiful local winery. Dove Valley Winery hosts a multitude of events year round for you and your company to enjoy. During your stay you will receive a free wine tasting voucher for each guest of age compliments of Dove Valley. Located 15 minutes from I95, Route 1, and one hour from Philadelphia and Baltimore. We may request a government issued ID upon booking.
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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.
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Popular amenities for Oakwood holiday rentals
Other great holiday rentals in Oakwood

Beautiful Creekside Cabin
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Secluded home pool & waterfall - Amish community
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Hill Top Cottage with Chickens!
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Sweet Little Farmhouse
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Creekside Cabin: Sauna | Hot Tub | Fire Pit |Cozy
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~Cedar Hill Cottage~
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Country Cape Cod, The Peddler House
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Applewood A-Frame Retreat + Hot tub
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Destinations to explore
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- Hersheypark
- M&T Bank Stadium
- Longwood Gardens
- Oriole Park at Camden Yards
- Federal Hill Park
- Johns Hopkins University
- Dutch Wonderland
- Hershey's Chocolate World
- Spooky Nook Sports
- CFG Bank Arena
- Betterton Beach
- University of Delaware
- Dover Motor Speedway
- French Creek State Park
- Roundtop Mountain Resort
- Marsh Creek State Park
- Patterson Park
- National Aquarium
- Greater Philadelphia Expo Center & Fairgrounds
- Valley Forge National Historical Park
- Ridley Creek State Park
- Arundel Mills
- Harbor East
- Elk Neck State Park





