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Holiday rentals in Oakwood

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Top-rated holiday rentals in Oakwood

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Guest favourite
An aerial view captures the spacious 4BR home surrounded by lush greenery and meadows. The multi-level decks and an outdoor dining area are visible, along with a fenced yard. The property features scenic farmland and trees, enhancing the rural landscape.
Home in Peach Bottom
4.89 out of 5 average rating, 109 reviews

Spacious, Quiet & Peaceful

Experience life in the country while staying in this beautiful 4BR home. Children totally love it here. ( 1.5 Acre fenced in yard to play in ) A fully functional kitchen & dining room. ( 2.5 Baths ) Spacious Family room, Living room, Children's playroom, & Spare room Located in real Amish farm country, A perfect spot for family or group events. A small creek in the backyard, ( Perfect for wading ) Multi-level decks w/ Weber grill overlooking the backyard & creek. 2 Horses & 3 Steers in meadows.

Top guest favourite
A serene waterfront view is captured at sunset, highlighting the calm water and a colorful sky filled with clouds. Several chairs are arranged near the water's edge, framed by lush trees and grassy areas.
Home in Perryville
4.97 out of 5 average rating, 151 reviews

Upper Chesapeake Getaway

Come relax with expansive views of the Upper Chesapeake with family or friends. Tucked away in Carpenter's point, you'll find peace watching boats pass by and local wildlife. The newly renovated home features newly 3BR, 1.5 Bath with a fully functional kitchen. You'll enjoy the beautiful sunrise views, water access, kayaks and deck. Local amenities include Great Wolf Water Park, Elk Neck State Park, local restaurants, and Perryville Casino. We welcome you to join the relaxing experience!

Top guest favourite
A rustic cabin is nestled among trees, elevated on a wooden deck. The vibrant red roof contrasts with the surrounding greenery. Four red chairs are arranged on the deck, providing a view of the natural landscape. Sunlight filters through the leaves, creating a serene ambiance.
Cabin in Airville
4.98 out of 5 average rating, 112 reviews

"ON THE ROCKS CABIN" the perfect getaway for 2!

Cabin is very charming, but rustic. Kitchen has full size frig, microwave, toaster oven, hot plate, toaster+ keurig. Coffee, condiments, soap & shampoo provided. There is a gas grill. Guests provide their qs sheets, towels, campfire wood & drinking water. A variety of dvd’s & games, hot water in & outside shower & tub. Tubes for floating provided, swim your own risk. Fire pit, creek is stocked. Steps to deck overlooking the creek.Trash goes home with guests, smoking on the decks only.

Top 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, 258 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 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, 113 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, 180 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.

Guest favourite
Cottage in Charlestown
4.96 out of 5 average rating, 259 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 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, 144 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
Home in Peach Bottom
4.97 out of 5 average rating, 117 reviews

Peaceful secluded home w/ heated pool & waterfall

Welcome to Quiet Brook Oasis Treat yourself to a relaxing weekend in this beautiful secluded creekfront home nestled in the woods that has a private inground pool, with a waterfall opened and heated all year. Located in peaceful Amish country, southern Lancaster county this newly remodeled home is sure to offer a relaxing and peaceful getaway. This is a perfect retreat for family or a couples romantic weekend. Find us on social media!

Top guest favourite
A wooden retreat is nestled among tall trees, showcasing a dark exterior with warm light glowing from within. An expansive deck extends in front, while a staircase leads down through lush greenery to the ground level, inviting access to the natural surroundings.
Cabin in Airville
4.98 out of 5 average rating, 152 reviews

Secluded Creek Cabin | Hot Tub + Firepit

✨Secluded Modern Creekside Cabin w/ Hot Tub✨ Escape to this luxury retreat in Airville, PA. Perfectly located for guests from NYC, Philadelphia & Baltimore. Unwind in the private hot tub, gather around the fire pit, and enjoy peaceful creek views. Featuring 3 queen beds, luxury linens, and spa-style amenities, this cozy, private cabin offers boutique comfort, ideal for romantic getaways or relaxing nature retreats.

Guest favourite
A bright and serene bedroom features a spacious bed with a light-colored quilt and decorative pillows. Two large windows offer natural light and views of lush greenery outside. A vintage dresser sits beside the bed, complemented by a nearby radiator.
Townhouse in Port Deposit
4.95 out of 5 average rating, 248 reviews

Quarry Landing • River Views in Historic Town

Enjoy easy access to everything from this perfectly located home. Quarry Landing is a turn-of-the-century Duplex filled with charm and beauty. Located on High Street in the quaint small town of Historic Port Deposit, (Maryland), perfect for couples or families. Great location in a safe neighborhood, short walk to local eateries, waterfront promenade, playground, fishing pier, dog park, and much more.

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, 312 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

  1. Airbnb
  2. United States
  3. Maryland
  4. Cecil County
  5. Oakwood