Vacation rentals in Oakwood

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Top-rated vacation rentals in Oakwood

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Guest favorite

An open kitchen area features a dark countertop and modern stainless steel appliances. Light cabinetry contrasts with a decorative brick column. Three wooden bar stools are positioned at the kitchen island, and natural light enters through the nearby door and window.

Home in Dayton

4.94 out of 5 average rating, 172 reviews

TOP AIRBNB IN DAYTON! | SOUTH PARK | FENCED YARD

Stunning Three Bedroom Historical South Park bungalow - located just steps away from UD, downtown Dayton, and Miami Valley Hospital. This home features an open concept living space with white oak hardwood flooring through-out. The kitchen is fully equipped with all the modern amenities: stainless steal appliances, soft close cabinetry, granite countertops. Two Gorgeous bathrooms w/ custom tile work including a master w/ walk-in shower. Completely fenced in rear yard w/ privacy. Magical space!

Top guest favorite

A spacious multi-level home is nestled among lush trees, surrounded by greenery. Large glass doors provide views of outdoor seating areas and the natural landscape. Decks and patios seamlessly integrate outdoor living with the serene woodland setting.

Home in Kettering

4.98 out of 5 average rating, 119 reviews

GORILLA HOUSE DAYTON

Private Spacious Multi-level 4 Bed 2/2 Bath Home on Wooded Lot. Walkout basement with bath, refrigerator, & wet bar. Fully equipped kitchen with everything you need to host family & friends. Perfect for dinner parties, SMALL events, special occasions, or just escaping for a getaway. NO CONGREGATING ON DRIVEWAY—be mindful of neighbor. Safe/quiet area. Pets considered with references, daily rate, & refundable deposit. Minutes from everything. EVERY STAY WE DONATE TO JANE GOODALL FOUNDATION.

Superhost

The kitchen features modern appliances, including a refrigerator and oven. A round table with two chairs is positioned by a window, allowing natural light to brighten the space. Light-colored cabinets and a ceiling fan enhance the airy atmosphere.

Home in Hamilton

4.82 out of 5 average rating, 112 reviews

Home Away From Home -Min to Downtown l Spooky Nook

Adorable newly remodeled house one block away from charming downtown Hamilton and only few min from Spooky Nook Sports Complex. This small community is the perfect mid western staycation destination with a bundle of cute small businesses within walking/biking distance. House offers super comfy new furniture and all the amenities to make your stay easy and enjoyable. Perfect for any group combination of friends or family, set up to accommodate children, no pets. Off street parking available.

Top guest favorite

Home in Hamilton

4.96 out of 5 average rating, 139 reviews

Cozy Cottage With A Pool

Kingston Cottage, centrally-located boho chic home in a quiet nook of Hamilton. We travel a lot and know what is important to make you feel safe and have a great adventure. Conveniently located to 4 major grocery stores, an abundance of uniquely amazing restaurants, Spooky Nook Sports Complex, downtown Hamilton, Miami University Hamilton and Miami University Oxford. Our home is the ideal place to unwind in a private relaxing oasis. We tried to think of everything for you, so you don't have to.

Guest favorite

The entryway features a vibrant blue door framed by large windows, allowing natural light to brighten the space. A stylish light fixture hangs from the ceiling. A wooden coat rack stands nearby, with a console table and decorative accents along the walls.

Home in Yellow Springs

4.92 out of 5 average rating, 158 reviews

*TOP Yellow Springs BnB*+Pet Friendly

The Wildflower House BnB offers an unbeatable location in the heart of downtown Yellow Springs, making it the perfect spot for your stay. Just steps away from the town’s best restaurants, unique shops, Glen Helen Nature Preserve, and the YS Fire House, it’s also directly across from the charming Mills Park Hotel. As the only rental home in the Village’s Business District, this exclusive retreat provides both convenience and character, immersing you in the vibrant energy of Yellow Springs.

Top guest favorite

A shaded front porch features two white rocking chairs positioned beside a vibrant flower pot filled with sunflowers. Green grass stretches beyond the railing, while trees create a serene backdrop.

Cottage in Springfield

4.97 out of 5 average rating, 177 reviews

Country cottage with beautiful view

Country cottage in wooded area overlooking a pond great for catch and release. Enjoy walking 2 miles of wooded trails, a front porch, side deck and fire pit area. Located close to local attractions: Downtown Springfield, Urbana and Yellow Springs; close proximity to Buck Creek State park and reservoir, George Rogers Park and the Fair at New Boston and Rock climbing at the Mad River Gorge. Located minutes from the Little Miami Bike trail network and canoe liveries on the Mad River.

Top guest favorite

A serene outdoor view showcases a well-maintained lawn bordered by trees. A tranquil pond reflects the sky, while a gazebo is placed nearby. A deck with outdoor seating is visible, enhancing the inviting outdoor space.

Guesthouse in Wilmington

4.98 out of 5 average rating, 103 reviews

The Tuscan-1.3 miles to W.E.C.

The Tuscan is unique, offering amenities seldom found in our area. Located 1.4 miles from the World Equestrian Center and 3 miles from Lake Cowan, to name a few, there is plenty to see and do within minutes of our location. Relax on your private deck or stay in and watch a movie on the Samsung Smart TV. Enjoy a serene country setting with tremendous views from every window. A great place to get away from it all. Once you stay, you will want to come back for another visit soon.

Top guest favorite

The charming exterior of the cottage features a uniquely shaped roof and a vibrant red door with a matching mailbox. A red bicycle with a wicker basket is positioned beside a tree, while greenery and flowers enhance the inviting entrance.

Home in Yellow Springs

4.98 out of 5 average rating, 192 reviews

The English Cottage - Enchanting, 1 block to town

Possibly the most charming home in Yellow Springs, one block to downtown. No expense was spared in restoring and renovating this 1800's cottage, with charming iron pane windows, original wood floors, screened porch, and fireplace. We lovingly renovated the kitchen, bathrooms and upstairs ensuite bed and bath. Two queen beds, luxurious linens, towels, fully equipped kitchen with Viking range, stainless steel appliances, & marble countertops. Not suitable for children under 12.

Top guest favorite

A spacious living area features exposed brick walls and a decorative fireplace with a modern black mantel. The room includes a wooden coffee table, a plush sofa, and a flat-screen TV mounted on the wall. A stylish staircase leads to the upper level, complemented by vibrant flooring.

Home in Dayton

4.97 out of 5 average rating, 275 reviews

Spacious 4BR/3.5BA Home Near UD, Oregon &DT Dayton

Situated in Dayton's historic South Park, this home, revamped in 2019, retains its 1800s charm. Ideal for families and friends keen on downtown Dayton proximity. Perfect for UD or local events, offering a homely feel. Please note: local bookings are not accepted. This neighborhood is currently undergoing revitalization, with several homes, including the one adjacent, at different stages of remodeling and rehabilitation. It's an urban area experiencing a dynamic transformation.

Superhost

The exterior of a single-story home features a brown brick facade with a welcoming front porch equipped with wooden railings. Well-maintained shrubs and grass enhance the landscaped yard, creating a neat and inviting entrance. Trees provide partial shade, adding to the serene environment.

Home in Dayton

4.88 out of 5 average rating, 138 reviews

The Wright Place B

4 bedrooms 3 full baths consisting of 4 King bedrooms. 1 Queen pull out Murphy bed. A crib located in the primary bedroom. Located mins away from University of Dayton, Wright state University and less than 30 mins from Wilberforce. Host home of the NCAA First Four Tournament. There are total of 5beds to sleep on based on 2 persons per bed. We also have sofa and you're welcome to use air mattress if you like in the laundry room. No more than 12 persons can stay per night.

Top guest favorite

The kitchen features modern wooden cabinetry and granite countertops, equipped with a stove, microwave, and refrigerator. Natural light is let in through a window, complemented by a decorative pendant light. A narrow passage leads to a door marked with ‘Laundry.’

Apartment in Monroe

4.98 out of 5 average rating, 126 reviews

Newly Remodeled Two Bedroom rental unit

Newly Remodeled, Pet Friendly, King & Queen Beds, Washer&Dryer in unit, Smart TV's in every room, Alexa, Keyless Entry. For children: high chairs, Pack and Play's with thick mattresses, Air Mattress. 2 miles from I-75, Close to Kings Island, Miami Valley Gaming Casino, Flea Markets, Premium Outlet Mall, Centrally located between Dayton and Cincinnati, 30 minutes to Cincinnati Reds, Bengals, Dayton Dragons. Close to Lebanon Sports Complex & Warren County Sports Park

Top guest favorite

Guesthouse in Downtown Dayton

4.97 out of 5 average rating, 101 reviews

NEW Oregon District Cozy Downtown Towhome

This guest townhouse is in the heart of the Oregon District, right next to all of Dayton’s best food & nightlife/events! The space is quaint and perfect for groups of 1-4, in a historic neighborhood, and incredible for quaint getaway. Please be aware that the other side of the home is also rented for guests, so while the spaces are completely separate, you may hear noise from other bookings. Please reach out if there are any issues. Come stay with us!