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
Bungalow in South Park
4.96 out of 5 average rating, 348 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.

Guest favourite
A modern kitchen features white cabinetry and a spacious central island with dark countertops. Stainless steel appliances are present, including a refrigerator and a built-in microwave. Two brown barstools are positioned at the island, with natural light filtering through nearby windows.
Home in South Park
4.94 out of 5 average rating, 204 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 favourite
A charming brick exterior of a home is highlighted with a black roof and neatly trimmed lawn. The property features a fenced yard and a driveway leading to the entrance, alongside well-maintained landscaping. An American flag is displayed near the entrance, indicating a welcoming atmosphere.
Home in Dayton
4.95 out of 5 average rating, 206 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!

Top Guest favourite
The open kitchen and living area feature a striking stone chimney column that divides the space. Modern stainless steel appliances are visible, alongside sleek granite countertops. Bar stools provide seating at the adjacent eat-in counter, and dark wood flooring complements the bright walls.
Home in South Park
5 out of 5 average rating, 169 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.

Guest favourite
Home in Dayton
4.95 out of 5 average rating, 194 reviews

Renshaw Ranch - Elegant King Bed Suite

Welcome to the Renshaw Ranch! Your own private home away from home with simple yet elegant touches throughout where you may find retreat and rest. Conveniently located for essentially any reason you have to visit the Dayton area; family, business, vacation or personal. You are minutes away from Kettering Hospital (3 min), Miami Valley Hospital (10min), I-75 (5 min), NCR (5 min), Dayton Mall, UD, WSU, WPAFB, restaurants and shopping, ie The Greene, Austin Landing, Oregon District and much more.

Top Guest favourite
The exterior of a charming gray house is presented, featuring white trim and dark shutters. A well-maintained front yard is adorned with vibrant rose bushes and a manicured lawn. The entrance is accessible via a set of steps, leading to a welcoming porch.
Home in Dayton
4.94 out of 5 average rating, 221 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.

Top Guest favourite
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.
Home in South Park
4.98 out of 5 average rating, 207 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!

Top Guest favourite
A fire pit constructed with stone outlines a warm flame, casting a glow in the foreground. Beyond, a lush green lawn transitions into a garden with colorful flowers and plants, framed by trees and a chain-link fence in the background.
Guest suite in Dayton
4.93 out of 5 average rating, 158 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!

Guest favourite
A serene outdoor space showcases a barrel sauna alongside comfortable wooden seating. The area is enhanced by vibrant green grass and warm cafe lights strung overhead, creating a relaxing atmosphere. A clear sky complements the setting, inviting guests to unwind in nature.
Home in South Park
4.95 out of 5 average rating, 173 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.

Top Guest favourite
Apartment in South Park
5 out of 5 average rating, 183 reviews

Take Flight

"Take Flight" is ready for you to enjoy during your stay in Dayton for work or play. Centrally located, this 2nd floor apartment is close to offices downtown, many nearby attractions, and main traffic arteries like I-75 and US 35. If you plan to stay in, Wi-Fi throughout the unit and a desk area in the bedroom can help you catch up on work. On the other hand, the 55" Smart TV, Blu-Ray player, books, movies and games are available if you'd rather relax.

Guest favourite
A spacious living area features a light-colored sofa and decorative cushions, arranged around a central round coffee table. Elegant artwork adorns the walls, and the room is illuminated by a modern chandelier. Window treatments offer privacy while allowing natural light to filter in.
Home in South Park
4.92 out of 5 average rating, 165 reviews

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.

Top Guest favourite
A spacious living area features a light-colored sectional sofa adorned with patterned cushions. A wooden side table stands nearby, and various plants add natural elements. Sunlight filters through sheer curtains, enhancing the bright ambiance of the room.
Home in Dayton
4.95 out of 5 average rating, 205 reviews

Well-Styled · King Bed · Fast Wi-Fi · Top Location

Welcome to La Belle Verde, a Guest Favorite in Dayton’s Historic St. Anne’s Hill. Built in the late 1890s, this home rests on a quiet, tree-lined street in one of Dayton’s most historic neighborhoods, it’s only minutes from downtown, the Oregon District, UD, and Miami Valley Hospital. Inside, history and comfort come together in 10-foot ceilings, windows that pour in natural light, and greenery that brings the home to life.

Popular amenities for Oakwood holiday rentals

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  2. United States
  3. Ohio
  4. Montgomery County
  5. Oakwood