Vacation rentals in Oakwood

4.96 out of 5 average rating, 297 reviews

Bungalow in Dayton

South Park Guest House

Historic South Park guesthouse. Built as the center of 3 sisters, this 1920 shotgun cottage and its neighbor to the right were bought by me, a neighborhood activist, who stripped them both down to the studs. What you'll find is a mix of historic, modern, and mid-century modern, with vaulted ceilings with skylights in both the bedroom and the spacious bathroom, and safe, snug, and quiet thanks to the insulation, new windows, new doors, and Berber carpet. Owned by a Certified Service Disabled Vet.

4.98 out of 5 average rating, 125 reviews

A welcoming entrance features a rustic wooden door painted in red, adorned with a wreath and a sign reading 'The Cranberry Cottage.' A vibrant yellow chair rests beside the door, and a colorful doormat greets visitors. The setting reflects a charming, cozy atmosphere.

Barn in Beavercreek

Quaint 1 bedroom barn cottage with lots of privacy

Welcome to the Cranberry Cottage! Enjoy the rustic barn experience while enjoying modern conveniences of this sweet romantic cottage. You'll feel like you're a million miles away from the hustle and bustle while you enjoy coffee on your own private deck. Walk up the path and cross the road and you can enjoy 150 acres with walking trails at Mount Saint John. Drive just 2 miles and you'll be close to the finest shopping and dining experiences at the Greene Mall. Come enjoy this unique experience.

A tastefully arranged living area is presented with two armchairs facing a coffee table. Abstract art adorns the wall, complemented by a lamp on a console table. Natural light enters through a window, enhancing the warm wood flooring and neutral color palette.

4.95 out of 5 average rating, 174 reviews

Private charming home w Fenced yard and fire pit

Chic Boutique is a lovely home in the heart of Dayton. Close to downtown, University of Dayton and both Miami Valley and Kettering hospitals. Our home is completely renovated and ready for your family to enjoy. We also have a fenced yard and parking in the driveway as well as on the street. You will love the private outdoor space for BBQ's or a cozy night lounging around the firepit. The kitchen is fully stocked for meal prep, and the kitchen table expands to seat 8 people. Relax and Enjoy!

5 out of 5 average rating, 128 reviews

Modern Historic House in the heart of South Park

Check out this stylish and modern home in the Historic South Park District centrally located in Dayton Ohio. Located on the best street in this trendy neighborhood where you can enjoy a view of the park from the porch. Built in 1880 this newly revamped home has an open concept full kitchen, 2 bedrooms and 2 full baths. Wood flooring and 12-foot ceilings throughout. Close to downtown, Miami Valley Hospital and the University of Dayton. Within walking distance to shopping, dining and much more.

4.9 out of 5 average rating, 126 reviews

Apartment in Dayton

Studio Neutral Chic near Kettering Hospital & Shop

Come enjoy this quaint unit in Kettering...close to shopping, restaurants, hospitals and city attractions! King size bed, balcony and tranquil essential oil diffuser will help set the mood and relax you during your stay! Walk or drive to various local and chain restaurants. 9 min drive to Kettering Hospital (main campus)...5 minute drive to The Greene Towne Centre. Visit Downtown Dayton/ Oregon District within 15 minutes. Hike Clifton Gorge in Yellow Springs within 30 min. 3 minute walk to pub

The open concept living space features vaulted ceilings with original exposed beams. A circular dining table and a comfortable seating area invite relaxation, while large windows allow natural light to fill the room. A sleek kitchen is visible, showcasing stainless steel appliances.

4.97 out of 5 average rating, 183 reviews

Oak Street Place in Historic South Park District

This is a one of a kind stay located in the heart of the historic South Park district. This unique property used to serve as several different types of businesses including a barbershop, grocery store and church. The space has now been completely remodeled into a stunning open concept home full of history and character. With ship lap walls and vaulted ceilings with original exposed beams, it looks like it could have been on an episode of HGTV’s Fixer Upper! Come stay at Oak Street Place!

An outdoor space features wooden lounge chairs arranged on green artificial turf. A wooden barrel sauna stands prominently, with a five-person hot tub nearby. Soft cafe lights hang overhead, creating a welcoming environment.

4.95 out of 5 average rating, 119 reviews

Luxury & Wellness

Discover a sanctuary of wellness and luxury in the heart of Dayton, Ohio. Our exclusive three-bedroom, two-bath home is not just a place to stay, it's an immersive bio-hacking experience designed to rejuvenate your mind, body, and soul. Here, health technology isn't just an amenity, it's a way of life offered to our guests at no extra cost. You have seen celebrities like Joe Rogan embrace these technologies on social media, and now it's your turn to experience their transformative power.

A circular dining table with plush, light-colored chairs is positioned in a well-lit space. The open kitchen features stainless steel appliances and bright cabinetry, while a cozy seating area with a gray couch is visible in the background, creating a welcoming atmosphere.

4.99 out of 5 average rating, 104 reviews

Cozy Beach House Minutes From Dayton!

Welcome and enjoy your trip in one of Dayton's best neighborhoods! Minutes from Dayton and a quick drive to the university. There is so much available at your fingertips. Wake up and grab a coffee at Warehouse 4. Stop by Trader Joes or Kroger to get your groceries. Take a walk through the many amazing parks nearby or catch a concert at Fraze Pavilion. After a day out, relax in the living room and watch your favorite shows or movies. Make yourself at home and live like a Dayton local!

4.94 out of 5 average rating, 151 reviews

Nerdy Neptune—Clean, Charming, & Central to Dayton

Welcome to Nerdy Neptune! A 1940s Cape Cod where we've kept all the charm, but updated the kitchen with granite countertops, a new stove and dishwasher, and 2 modern bathrooms. Sleeps up to 10 (1K, 1Q, 1F, 2T, 2 Couches). This cozy home in Patterson Park is minutes from all things Dayton including UD, Oakwood, Wright State, & Downtown. We pride ourselves on cleanliness and having a fully stocked kitchen! If there's anything you need, just give us a shout—we live around the corner.

Guesthouse in Downtown Dayton

4.97 out of 5 average rating, 103 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!

Guesthouse in Centerville

5 out of 5 average rating, 186 reviews

The Carriage House in Historic Uptown Centerville

Welcome to the Carriage House. Walk to shops, restaurants, ice cream & more! Whether you're staying for a fun weekend, romantic get away, work or visiting family and friends- the Carriage House is the perfect place. The Carriage House was built in 1897 & underwent a complete renovation in 2017. With its open style concept & 12 ft ceilings, it has taken on a whole new role as one of Centerville's coziest getaways, in the heart of Uptown.

A modern dining area features a wooden table surrounded by six chairs, set against a dark wall. A light fixture hangs above, while a sideboard and decorative items add warmth to the space. An open kitchen is visible in the background, showcasing dark cabinetry and bar stools.