Holiday houses in Oakwood

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.

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!

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.

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!

Vagabond’s Tiny Art Gallery BnB

Vagabond offers a cozy stay and light breakfast in an INCLUSIVE and WELCOMING mellow, private Tiny Art Gallery BnB. Located on a tree lined street in a 1940’s neighborhood, walking distance to Trader Joes, restaurants, boutiques, Fraze Pavillion and Lincoln Park. 10 minute commute downtown to sites like; UD, Dayton Art Institute, Carillon Historic Park, Levitt Pavilion, Oregon District, Front Street, Schuster, Riverscape, etc. Don’t miss Dayton’s stellar local arts and music scene!

Historic & Eclectic Apt in the Heart of Huffman!

A new space inviting you to experience all that Historic Huffman and the surrounding neighborhoods have to offer! Located in a 140 year old building, this recently renovated unit has been given new life and is ready to welcome you to the Gem City. If you're here for business, visiting friends, or attending a wedding at The Lift or one of downtown's many venues, this centrally located space is a great place to kick-back and relax. Please read House Manual prior to booking. Thank you!

Root2Rise Quiet, Clean, Prime Location, 2 bedroom

Enjoy your own two-bedroom, first floor apartment in a quiet four-unit building. It is modestly decorated, squeaky clean and cozy. This location could not be more convenient! Walking distance to two grocery stores, retail shopping, and The Fraze Pavilion. Ten minute drive to Kettering Hospital, Miami Valley Hospital, downtown Dayton and University of Dayton. 15-20 minute drive to the Wright Patt Air Force base. Furnished and equipped with everything you need.

South Park- The Purple Barney Guesthouse

Historic South Park Purple Barney guesthouse. Built in 1920 this shotgun cottage was rehabbed by me, a neighborhood activist, who stripped it down to the studs. What you'll find is a mix of historic, modern, and mid-century modern, with vaulted ceilings, skylights in both the bedroom and the spacious bathroom, and safe, snug, and quiet thanks to the insulation, new windows & doors. New Metal Roof in 2022! Your host is a Certified Service Disabled Vet.

Dayton Retreat, UD, MVH, Oregon Dist, KHN, &WPAFB

Welcome to Polu, named after the Hawaiian word for “blue.” Located in Dayton’s historic South Park district, this beautifully restored 1800s home blends original architectural charm with modern luxury. Step inside to tall ceilings, preserved vintage details, and elegant, thoughtfully curated décor. Designed for comfort and relaxation, Polu offers a serene and stylish retreat whether you’re visiting for business, a weekend getaway, or a special event.

The Aviator Bungalow in Kettering

Our Aviator Bungalow in Kettering, Ohio is close to Carillon Park and University of Dayton. You will feel right at home with the amenities we offer. Our place is great for couples, solo adventurers, travelling nurses, doctors, therapists and business travelers. A nice city park is right across the street with a tennis court and basketball court, shelter and grill. Five minutes to University of Dayton/Downtown Dayton.

Carillon Cottage - Modern Comfort & Vintage Design

Carillon Cottage is a historic home featuring modern comfort with vintage design. This family-friendly and spacious house, which was originally built in 1905 and fully renovated in 2023, is filled with details highlighting the rich history of Dayton, Ohio. Enjoy the curated display of local photos and elegant furnishings with classical touches. We look forward to hosting you!

Petite Paradise: Tiny Home Vibes! Great Location!

Tiny Home! Enjoy 420 sq home, a private fenced-in yard for your furry friends! Relax on the spacious sun deck or take advantage of the large side yard—ideal for running and playing with your dog. Plus, unwind by the cozy fire pit with provided wood and a swing for ultimate relaxation. Perfect for pet owners and nature lovers alike!