Vacation rentals in Oakwood

4.98 out of 5 average rating, 130 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, 177 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, 133 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.

A clean bathroom is presented, featuring a white vanity with ample storage and a round mirror above the sink. A toilet is situated next to the vanity, with beige towels hanging nearby. A decorative basket adds a touch of style against the patterned floor.

4.93 out of 5 average rating, 111 reviews

BRIGHT~AIRY Loft - near Downtown/UD/UVM

Bright, open upstairs apartment in circa 1860 federal style building with high ceilings and lots of natural light. Located a 3 minute walk from Miami Valley Hospital in Historic South Park. Close to the University of Dayton, shops on Brown Street, Interstate 75, the Oregon District and Downtown Dayton. South Park is one of the most popular neighborhoods in Dayton. Walk or bike anywhere. The unit below is currently undergoing work, some noise is to be expected. Only during daytime hours :)

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, 185 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.

4.94 out of 5 average rating, 124 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, 108 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!

A wooden shelf displays a set of clear glasses alongside a collection of cookbooks in yellow, white, and brown covers. A bright turquoise kettle adds a pop of color, enhancing the modern kitchen's thoughtful design.

4.94 out of 5 average rating, 154 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

4.96 out of 5 average rating, 109 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!

4.88 out of 5 average rating, 237 reviews

A street view captures charming storefronts with striped awnings and decorative street lamps lining the sidewalk. Lush greenery is visible near the curb, while parked cars dot the area. The scene reflects a vibrant, walkable community ambiance, with clear skies overhead.

Apartment in Kettering

Shopping Paradise | Free coffee + Parking

Welcome to this cozy and contemporary 2-bedroom apartment, perfectly located for a relaxing and convenient stay. With spacious bedrooms, a fully equipped kitchen, and modern amenities, this space offers a peaceful retreat just steps from Dayton's premier shopping mall. Ideal for families, couples, or business travelers, you'll enjoy proximity to retail stores, dining, and entertainment options—all within walking distance.

Guesthouse in Centerville

A cozy living area features a large television mounted on a light green wall. A white table with two chairs and a vintage-style lamp are visible, along with burnt orange and white accent furniture. A decorative cowhide rug is placed on the warm wood floor.

5 out of 5 average rating, 196 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, 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.

4.98 out of 5 average rating, 187 reviews

TOP AIRBNB IN KETTERING! | Near Downtown Dayton!

Gorgeous, professionally remodeled home on a quiet street in Kettering -- located just minutes away from University of Dayton, Carillon Historical Park, Oakwood, and downtown Dayton. This home features a fully fenced in backyard, gourmet kitchen, completely new bathrooms, and so much more. If you are looking for an amazing, over-the-top, 5 star experience -- give us an opportunity!

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Other great vacation rentals in Oakwood

The entrance sign of Patterson Park is displayed prominently on a natural stone. The sign features wooden elements with white lettering. Surrounding foliage includes green plants and bright orange flowers, contributing to the park's inviting atmosphere. A residential street lined with cars is visible in the background.

4.93 out of 5 average rating, 29 reviews

Patterson Park Cottage

RobertRating, 5 stars1 month ago

It took some logistics to support 5 men on a trip, but this one did. Nice quiet place in south Dayton. All went better than expected.

A spacious pavilion is supported by sturdy stone and wooden columns, set in a grassy area. Picnic tables are arranged beneath the roof, offering shade in an open environment. Lush trees and a park setting are visible beyond the pavilion, creating a serene outdoor space.

5 out of 5 average rating, 11 reviews

Beautiful 1 Bed Near Hospitals and U of Dayton

KristyRating, 5 stars2 months ago

Great place especially for the price. It’s close to a lot but in a nice quiet neighborhood. Christina is a great host! Very responsive and helpful, I enjoyed her hosting so much that I’m staying in another one of her units haha. I Highly recommend.

A private backyard space is illuminated by soft string lights at twilight. A fire pit sits at the center surrounded by cushioned seating, inviting relaxation. Wooden fences enclose the area, enhancing the sense of privacy. The serene ambiance is complemented by the evening sky.

4.86 out of 5 average rating, 255 reviews

Cozy 2BR | Fenced Yard & Fire Pit | Walk to UD

HankRating, 5 stars2 weeks ago

Space was perfect for us while we visited family nearby. Location was great, backyard was perfect for us n dogs to hang out. Loved the kitchen n rooms. Would definitely stay here again next time we come to Dayton.

A bright and airy living area features a comfortable sofa adorned with decorative pillows. A glass coffee table accompanies a green accent chair, while a dining set for four is positioned near large windows. Light drapes enhance the space's welcoming ambiance.

4.88 out of 5 average rating, 64 reviews

Cozy in Dayton Unit #4

RoryRating, 5 stars6 days ago

Aaron's place was exactly what we needed. Great location, quiet and comfortable. It was our first time staying there and we will definitely look to stay there again.

Superhost

The exterior of the apartment building is depicted, featuring a two-story structure constructed of yellow brick. Steps lead to the entrance, framed by shrubs and grass. Large windows with black shutters are visible, along with a small tree on the side, contributing to the neighborhood's character.

4.71 out of 5 average rating, 72 reviews

*Cozy-Comfortable 2 Bedroom Kettering Apartment!*

JohnRating, 5 stars1 week ago

Megan was a wonderful host and very responsive to messages. We enjoyed our stay. If you like to walk, bike or run, there’s a nice trail very close to the building. The neighborhood was quiet and we almost never heard another tenant in the building. Overall, it was a great experience.

A small laundry area is visible, featuring a neatly organized countertop. A sign labeled 'Self Service Fluff and Fold, Open 24 Hours a Day' hangs above. An iron is positioned on the counter, alongside a basket and a decorative mat with the same lettering.

5 out of 5 average rating, 87 reviews

Carillon Cottage - Modern Comfort & Vintage Design

TuanRating, 5 starstoday

Greg’s place is a true gem. The renovation preserved the home’s character while adding a touch of modern charm. The spotless and elegantly decorated interior beautifully showcases Dayton’s rich heritage. The hosts are responsive, kind, and super helpful. If you have the chance, be sure to stay here.

5 out of 5 average rating, 73 reviews

A spacious sectional couch in a neutral tone occupies the lower level, complemented by soft carpeting. Decorative blue pillows add a pop of color. A small table is visible in the background, illuminated by natural light filtering through windows near the ceiling.

Home in Kettering

Book Lover's Bungalow

GwendolynRating, 5 stars1 week ago

The booklovers bungalow was affordable, convenient, and very comfy. We were out and about all weekend but enjoyed a quiet coffee on the porch and the comortable beds. Wish we had had more time to play a game or watch a movie in the cool, spacious basement. Thanks for a great space for the family to gather!