Vacation rentals in Oakwood

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Top-rated vacation rentals in Oakwood

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

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Guest favorite

Bungalow in Dayton

4.96 out of 5 average rating, 240 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.

Dec 1 – 8

G$20,368 GYD per night

Guest favorite

Home in Dayton

5.0 out of 5 average rating, 13 reviews

Willow Cottage

Eclectic, adorable and cozy cottage with three levels of living space. Located in a well established, neighborhood where many professionals call home; you can feel safe walking outdoors any time of the day or night. Close to downton Dayton, UD and 20 minutes from WPAFB. There are outdoor concernts 5 minutes away all summer. Ten mins. from The Greene, an outdoor mall with plenty of shopping and entertainment. All 8 hospitals are located within 15 minutes including Dayton's Children's Hospital.

Jul 15 – 22

G$24,504 GYD per night

Guest favorite

Home in Dayton

4.97 out of 5 average rating, 116 reviews

Private fenced yard with furnished patio/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!

Jul 27 – Aug 3

G$31,866 GYD per night

Guest favorite

Home in Dayton

4.97 out of 5 average rating, 158 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!

Aug 8 – 15

G$30,099 GYD per night

Guest favorite

Apartment in Dayton

5.0 out of 5 average rating, 31 reviews

Traveling Nurse's Sanctuary (The Urban Suburban)

Location Location Location! The Urban Suburban a Private entrance apartment on very quiet dead end street perfect for someone working 3rd shift. Fully equipped kitchen, including coffee maker, plates, glasses, silverware, pots & pans, etc. The apartment also has a full size washer and dryer. There is convenient off-street parking right next to unit for a small to midsize vehicle, and a partially fenced small yard. Ask about our health care workers discount for stays of 3 months or more.

May 31 – Jun 7

G$21,422 GYD per night

Guest favorite

Home in Dayton

4.94 out of 5 average rating, 126 reviews

Perfect Little Gem

Cute 2 bedroom home with two parking spaces in front of garage and plenty of free street parking. A mile from the University of Dayton, Miami Valley Hospital, 10 Wilmington Place, Oregon District, South Park and Downtown Dayton. Home has 2 queen size beds. Covered front porch and a fenced in backyard. A lot of guest ask this; we have a Keurig and a standard Mr.coffee pot. The home always has 4-6 Keurig pods and sometimes has local specialty ground coffee. Let us know if you prefer ground.

Nov 17 – 24

G$25,106 GYD per night

Guest favorite

Home in Dayton

4.95 out of 5 average rating, 271 reviews

“Helen’s House” Granny Chic 2 Baths 2 Beds

Helen's House is ideally located in Southeast Dayton near the I-75 interchange. Just 1.5 miles from the city center. Close to the University of Dayton Campus, Wright Patterson Air Force Base, the historic Woodland Cemetery. Grocery stores and restaurants are 2-10 minutes from the home. Built in 1900 with original woodwork and wallpaper, we offer the ultimate Granny Chic experience and a step back in time. Helen's House is perfect for couples, adventurers, business travelers, and families.

Apr 19 – 26

G$21,718 GYD per night

Guest favorite

Home in Dayton

4.93 out of 5 average rating, 186 reviews

Entire house- Dayton/U D /KETTERING/OAKWOOD /WPAFB

Near UD Oakwood. 2 Bedrooms. We NEVER Cancel your reservation..3 Smart TV's High-Speed Internet Kettering & Miami Valley Hospitals . 2 minutes to UD, 15 minutes to the airport. Kitchen, Dining Rm, Living Rm, 2 bedrooms. 10 min.WPAFB. 1 queen 2 twin. Squeaky clean Great eating & shopping near. Screened porch. Quiet street.. close to everything...Next to Oakwood in Next to Oakwood & Dayton located in Kettering. Near all major highways. No UD parties Some pets permitted contact us.

Dec 13 – 20

G$45,256 GYD per night

Guest favorite

Apartment in Dayton

4.92 out of 5 average rating, 12 reviews

Greenmount's Cove *5 mins from UD*

Our charming AirBnb is nestled above our personal family home and offers the perfect blend of comfort and warmth. The thoughtful touches throughout the space reflect the care we've put into creating a home away from home for our guests. Step outside to explore the surrounding neighborhood or bask in the tranquil garden attached to the family home. Whether you're here for a weekend getaway or an extended stay, our place invites you to enjoy the privacy of your own retreat!

Nov 18 – 25

G$13,699 GYD per night

Guest favorite

Guest suite in Dayton

4.92 out of 5 average rating, 87 reviews

Vagabond’s Tiny Art Gallery BnB

Vagabond offers a cozy stay and BREAKFAST in 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!

Jul 26 – Aug 2

G$17,605 GYD per night

Guest favorite

Home in Dayton

4.99 out of 5 average rating, 146 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!

Nov 19 – 26

G$50,367 GYD per night

Guest favorite

Home in Dayton

5.0 out of 5 average rating, 42 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!

Sep 22 – 29

G$32,322 GYD per night