Holiday houses in Oakwood

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Top-rated holiday rentals in Oakwood

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

A spacious living area is equipped with a comfortable leather sofa and contemporary wooden furniture. A large television is mounted on the wall, while a stylish round coffee table sits in the center. Natural light enters through two windows, enhancing the neutral color palette.

Bungalow in Dayton

4.96 out of 5 average rating, 360 reviews

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.

LocationFamilyQuiet

Top Guest favourite

The open-concept kitchen and dining area features modern appliances and a large dining table with white chairs. Natural light fills the space through two windows, with blue curtains adding a pop of color. A stylish chandelier hangs above the table, complementing the contemporary design.

Home in Dayton

4.98 out of 5 average rating, 50 reviews

5 min to UD, Fire Pit, Fenced Yard, No Airbnb Fees

This newly renovated comfortable 2 bedroom 1 bath bungalow in a quiet, well established residential neighborhood is 5 min to WPAFB and 7 min to UD and downtown Dayton. Enjoy the queen size bedroom, second bedroom with two full size beds, brand new kitchen and bathroom, and relaxing fire pit in the backyard. Fully equipped kitchen, and Keurig pod and drip coffee! This centrally-located home sleeps up to six and is the perfect location for your family or co-workers to enjoy your stay in Dayton.

LocationFamilyLong stay

Guest favourite

A welcoming living room features a black couch, two light-colored club chairs, and a coffee table on a woven rug. Natural light fills the space through large windows adorned with white drapes. A decorative mirror and side table enhance the room's charm.

Home in Dayton

4.94 out of 5 average rating, 210 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!

ValueLocationAmenities

Top Guest favourite

Home in Dayton

4.94 out of 5 average rating, 223 reviews

In Kettering Near UD/Oakwood/Hospitals & Dayton

UD :University of Dayton,Kettering Oakwood. squeaky clean. 3 Smart TV's "High-Speed" Internet Minutes from Children's, Kettering & Miami Valley Hospitals .15 minutes: (DAY)Dayton Airport. :(CVG) Cincinnati Airport 55 min . Kitchen, Dining Rm, Living Rm, 2 bedrooms. work desk entire house! WPAFB museum,Grocery & shopping near. free parking.Screened porch. Quiet street.. Kurig coffee... located :Kettering. Near all major highways....bike paths, parks, hiking No parties Pets on approval.

ValueLocationParks

Top Guest favourite

A charming red-brick home is surrounded by lush greenery and colorful flower gardens. A stone pathway leads to the entrance, complemented by various potted plants. A small friendly dog is seen resting on the pathway, adding a welcoming touch to the serene outdoor space.

Guest suite in Dayton

4.94 out of 5 average rating, 171 reviews

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!

LocationFamilyParks

Superhost

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.

Home in Dayton

4.93 out of 5 average rating, 181 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.

ValueLocationKitchen

Top Guest favourite

The airy living room features an oversized couch, a mounted TV, and two blue armchairs. Natural light enters through large windows, highlighting the hardwood flooring. A door leads to a spacious backyard, while a light fixture provides soft illumination.

Home in Dayton

4.99 out of 5 average rating, 165 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!

LocationFamilyAmenities

Guest favourite

A stylish living area features a modern circular ceiling light above a round black coffee table. A plush, curved white armchair provides seating near a cozy electric fireplace, while a large television is mounted on the wall. The space benefits from natural light, enhancing its warmth.

Home in Dayton

4.96 out of 5 average rating, 74 reviews

Blue Bungalow, South Park, Oregon dist, UD, MVH

🏡 Stylish Historic Bungalow Near UD, Hospitals, Wedding Venues & Downtown – Walkable South Park Welcome to your cozy home-away-from-home in Dayton’s charming 🌳 South Park Historic District! This beautifully renovated 2-bedroom bungalow offers the perfect balance of historic charm and upscale modern living — ideal for medical professionals, university visitors, wedding guests, or anyone wanting a stylish, comfortable retreat.

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Top Guest favourite

Bungalow in Dayton

4.97 out of 5 average rating, 172 reviews

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.

LocationValueSleep quality

Guest favourite

The exterior of the tiny home is showcased, featuring a dark green wooden facade. A single door with six panels stands prominently, complemented by a small window. Planters with greenery are positioned beside the entrance, and a wooden deck extends from the front, partially covered by snow.

Home in Dayton

4.95 out of 5 average rating, 102 reviews

Tiny Home fit for a King: Near Belmont Park!

Welcome to Tiny Home for a King, a stylish 472 sq. ft. retreat in Dayton perfect for solo travelers or couples. This thoughtfully designed space blends modern amenities with charming details, offering a cozy and comfortable atmosphere ideal for relaxing, recharging, or simply feeling at home. Everything you need for a memorable stay is right here in this tiny but inviting haven.

ValueLocationAccuracy

Top Guest favourite

The exterior of Carillon Cottage features a striking blue facade with white trim, set against a backdrop of lush greenery. The structure displays a classic gable roof, with multiple windows allowing for natural light. A stone wall borders the front garden, which is accentuated by small, neatly trimmed hedges.

Home in Dayton

4.99 out of 5 average rating, 139 reviews

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!

LocationFamilyCondition

Top Guest favourite

Guesthouse in Centerville

5 out of 5 average rating, 291 reviews

Centerville Carriage House in Uptown

Escape to one of Uptown Centerville’s most charming hidden gems….just steps from local restaurants, cozy coffee shops, unique boutiques, and a scoop (or two) of Graeter’s Ice Cream. Whether you’re planning a romantic getaway, visiting family, or simply looking to relax, this cozy retreat is the perfect place to unwind while walking to everything Uptown has to offer.

LocationFamilyCondition