Vacation rentals in Oakwood

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Top-rated vacation rentals in Oakwood

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Guest favorite
The front porch is illuminated by the warm glow of sunset, highlighting the textured walls and inviting seating area. Lush greenery is visible along the edges, and a large tree stands in the yard, framed by a peaceful rural landscape.
Farm stay in Holtwood

NorthsideInn: near sight and sound & sickmans mill

Relax and unwind at Northside Inn. Located on a 122 acre working farm, it is great for couples, or spacious enough for groups, showers, or have a meeting at our 11.5ft table. This farm marks the highest elevation of tillable farm ground in Lancaster County, allowing you to enjoy all the views! From the wide open fields, to the gorgeous sunsets, then when the sun goes down look to the North and see the lights of Lancaster city. You will definitely see an Amish buggy pass by during your stay.

4.88 out of 5 average rating, 384 reviews
Top guest favorite
A single-story brick home is set against a bright blue sky, flanked by large trees. One side features a majestic flowering tree with pink blossoms, while the other is shaded by a leafy tree. Solar panels are visible on the roof.
Home in Rising Sun

“Home Away from Home” in Rising Sun, Maryland

PLEASE READ *BEDROOM 3 is a suite that can be added for an extra charge (see pics) * It includes a living area, king size bed, bathroom and kitchenette. Ask Karen for pricing to add. Without the suite there is a foyer leading to a large living room, kitchen with dining area, 2 bedrooms with queen beds and a full bath. This home is comfy and has a history room showing family collectibles dating back to 1854.... Children under 12 years of age are not suitable and No Pets are allowed.

4.96 out of 5 average rating, 336 reviews
Guest favorite
Home in Peach Bottom

Secluded home with 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. THE POOL IS HEATED ALL YEAR!! (So yes you may swim in the winter! ) 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!

4.96 out of 5 average rating, 135 reviews
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

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.

4.98 out of 5 average rating, 288 reviews
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

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.

5.0 out of 5 average rating, 129 reviews
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

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.

4.94 out of 5 average rating, 102 reviews
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

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.

5.0 out of 5 average rating, 220 reviews
Guest favorite
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

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.

4.89 out of 5 average rating, 125 reviews
Top guest favorite
A panoramic view showcases a cozy two-story house set against a serene waterfront backdrop. Colorful autumn foliage lines the shore, reflecting vibrant hues in the calm water. A grassy area with a small beach adds to the inviting outdoor space, perfect for relaxation.
Home in Perryville

Top of the Chesapeake - Private Waterfront Home

Our house is nestled between the shore of the NE River and the creek and marsh directly behind. The home is warm, unassuming and inviting; you'll feel right at home. Perfect for familes or groups, or a romantic weekend. Bird watchers will love the bald eagles, ospreys, kingfishers, mallards and cormorants, to name a few. The upstairs living room is a perfect place for the kids while the adults enjoy the lower area. You find our place warm, cozy and quiet.

4.92 out of 5 average rating, 248 reviews
Top guest favorite
Home in Whiteford

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.

4.96 out of 5 average rating, 105 reviews
Guest favorite
A cozy bedroom features a double bed with a light quilt and decorative pillows. Natural light filters through two sets of white wooden blinds, enhancing the calming blue walls. A bedside table with a small lamp is positioned next to the bed.
Home in Port Deposit

Port Right Side *easy stay near 95* Port Deposit

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). Safe neighborhood, short walk to local eateries, waterfront promenade, playground, fishing pier, dog park, and much more. Perfect for couples or families. Spacious 3 bedroom / 1 bathroom, well-stocked kitchen, beautifully decorated, and comfortable mattresses.

4.87 out of 5 average rating, 124 reviews
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

Syd 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.

4.98 out of 5 average rating, 321 reviews

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