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Holiday houses in Oakwood

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Top-rated holiday rentals in Oakwood

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

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Top Guest favourite
A spacious family room features a comfortable sofa and a cozy armchair, with natural light flowing through a large skylight and sliding glass doors. The open kitchen is visible in the background, showcasing modern appliances and a welcoming layout. A neutral area rug enhances the warmth of the space.
Home in New Providence
5 out of 5 average rating, 109 reviews

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

Top Guest favourite
Cabin in Wrightsville
4.98 out of 5 average rating, 249 reviews

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

Top Guest favourite
Home in Quarryville
4.97 out of 5 average rating, 109 reviews

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.

Top Guest favourite
A modern kitchen area features stainless steel appliances, including a commercial stove range. A centrally positioned island is surrounded by bar stools. Natural light fills the space through two windows, while a cozy seating area with a gray sofa and a warm rug enhances the inviting environment.
Home in Aberdeen
4.96 out of 5 average rating, 203 reviews

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.

Guest favourite
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, 279 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 favourite
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 favourite
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, 127 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 favourite
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, 208 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 favourite
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 favourite
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
4.92 out of 5 average rating, 159 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.

Guest favourite
A welcoming living area presents a light-colored sofa and two upholstered chairs, arranged around a dark coffee table on a patterned area rug. Wall art features nature themes, and a stone accent wall adds texture. Natural light flows through the nearby windows.
Farm stay in Rising Sun
4.92 out of 5 average rating, 173 reviews

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.

Top Guest favourite
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, 318 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 holiday rentals