A large, stately building with a symmetrical facade, columns, and a central pediment.

Oakwood Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Oakwood vacation rentals

1. Historic Oregon District

Historic Oregon District
Downtown Dayton
9.8 out of 10, Exceptional, (86 reviews)
"A bright little apartment with easy walking access to Fifth St and throughout a beautiful old residential neighborhood."
United States
Keith
The price is CA $111
CA $173 total
includes taxes & fees
Aug 30 - Aug 31
Historic Oregon District

2. Updated Historical apartment close to a park and two blocks from the best dining

Updated Historical apartment close to a park and two blocks from the best dining
Downtown Dayton
10.0 out of 10, Exceptional, (120 reviews)
"Great place. Clean, in great shape and close to UD!!"
United States
Paul B.
The price is CA $111
CA $173 total
includes taxes & fees
Sep 1 - Sep 2
Updated Historical apartment close to a park and two blocks from the best dining

3. The Castro

The Castro
Walnut Hills
8.6 out of 10, Excellent, (12 reviews)
"Our visit was very pleasant ! Loved the vibe and the books:) very quiet neighborhood and host was available during the late night arrival to answer questions. "
United States
Alyssa B.
The price is CA $83
CA $222 total
includes taxes & fees
Sep 9 - Sep 10
The Castro

4. Steps away from Dayton’s Historic Oregon District

Steps away from Dayton’s Historic Oregon District
Downtown Dayton
10.0 out of 10, Exceptional, (4 reviews)
"Very cool historic neighborhood! Awesome restaurants in walking distance!"
United States
James c.
The price is CA $114
CA $239 total
includes taxes & fees
Aug 31 - Sep 1
Steps away from Dayton’s Historic Oregon District

5. Oregon District I Free Parking I Getaway

Oregon District I Free Parking I Getaway
Downtown Dayton
9.0 out of 10, Wonderful, (18 reviews)
"Very beautiful location with lots of walkable restaurants."
United States
Daniel Moorman
The price is CA $146
CA $273 total
includes taxes & fees
Aug 29 - Aug 30
Oregon District I Free Parking I Getaway

6. Gem City Haven

Gem City Haven
Linden Heights
9.2 out of 10, Wonderful, (16 reviews)
"The house was very clean and local to the attractions we needed for the weekend "
United States
Kirsten R.
The price is CA $109
CA $206 total
includes taxes & fees
Sep 2 - Sep 3
Gem City Haven

7. Cozy Historic Home | Historic Oregon District

Cozy Historic Home | Historic Oregon District
Downtown Dayton
10.0 out of 10, Exceptional, (7 reviews)
"Walking distance to the Oregon District. Clean and had everything we needed for our short stay. "
United States
Beth M.
The price is CA $119
CA $251 total
includes taxes & fees
Aug 30 - Aug 31
Cozy Historic Home | Historic Oregon District

8. Ruby Red Haven – Chic Downtown Retreat Dayton

Ruby Red Haven – Chic Downtown Retreat Dayton
South Park
10.0 out of 10, Exceptional, (1 review)
"It was amazing "
United States
Joslyn M.
The price is CA $139
CA $258 total
includes taxes & fees
Aug 30 - Aug 31
Ruby Red Haven – Chic Downtown Retreat Dayton

9. Walk to Dining & Attractions | Free Coffee

Walk to Dining & Attractions | Free Coffee
Downtown Dayton
8.8 out of 10, Excellent, (6 reviews)
"Loved the Oregon district. Can walk to many shops and restaurants. "
United States
vince H.
The price is CA $111
CA $229 total
includes taxes & fees
Sep 1 - Sep 2
Walk to Dining & Attractions | Free Coffee

10. Cozy apartment #4

Cozy apartment #4
North Riverdale
9.2 out of 10, Wonderful, (5 reviews)
"I had a very nice comfortable 4-day stay in the apartment I got there it was very clean very nice like the layout very pet friendly my dog enjoyed himself there it was nice location centrally located to places I wanted to go to I would recommend this to other people"
United States
Anthony U.
The price is CA $80
CA $226 total
includes taxes & fees
Sep 4 - Sep 5
Cozy apartment #4

11. Boho loft is a fabulous 2-bedroom apartment close to downtown

Boho loft is a fabulous 2-bedroom apartment close to downtown
Twin Towers
9.0 out of 10, Wonderful, (2 reviews)
"Love the eccletic feel of the space. As described and close to things to do in the area!"
United States
Angela D.
The price is CA $137
CA $280 total
includes taxes & fees
Sep 1 - Sep 2
Boho loft is a fabulous 2-bedroom apartment close to downtown

12. Twinkle, twitch and stay awhile/ Bewitched Inspired 2 bedroom apartment

Twinkle, twitch and stay awhile/ Bewitched Inspired 2 bedroom apartment
Walnut Hills
The price is CA $133
CA $293 total
includes taxes & fees
Aug 30 - Aug 31
Twinkle, twitch and stay awhile/ Bewitched Inspired 2 bedroom apartment

13. Cozy, Renovated 3-Bedroom in the Heart of Dayton

Cozy, Renovated 3-Bedroom in the Heart of Dayton
Walnut Hills
7.4 out of 10, Good, (3 reviews)
"It was an alsome experience no bad complaints"
United States
Jayciona
The price is CA $150
CA $366 total
includes taxes & fees
Sep 2 - Sep 3
Cozy, Renovated 3-Bedroom in the Heart of Dayton

14. Cowboy Cottage country charm in the city

Cowboy Cottage country charm in the city
Walnut Hills
6.0 out of 10, (11 reviews)
"Clean and cozy….nice stay overall"
United States
Aaron F.
The price is CA $109
CA $248 total
includes taxes & fees
Aug 31 - Sep 1
Cowboy Cottage country charm in the city

15. Gorgeous Private Studio in heart of Kettering

Gorgeous Private Studio in heart of Kettering
Dayton
9.0 out of 10, Wonderful, (7 reviews)
"Very clean and quiet. Would definitely stay there again."
United States
Linda D.
The price is CA $150
CA $288 total
includes taxes & fees
Sep 1 - Sep 2
Gorgeous Private Studio in heart of Kettering

16. Historical Louisiana Style Home

Historical Louisiana Style Home
Walnut Hills
9.0 out of 10, Wonderful, (18 reviews)
"My husband and I were in town for a long weekend watching a tournament at University of Dayton. This home was small but the location was perfect for what we needed, we were very close to campus and also to many of the best restaurants, shopping and nightlife. With the unique layout of the home, having to walk through one bedroom to get to the other, I would not recommend to more than a couple or maybe small family. It worked perfectly for us and we would definitely stay again should we be back...
United States
Kathryn J.
The price is CA $159
CA $341 total
includes taxes & fees
Aug 31 - Sep 1
Historical Louisiana Style Home

17. The Jackie O ~ One Bedroom Relaxing Retreat

The Jackie O ~ One Bedroom Relaxing Retreat
Walnut Hills
7.6 out of 10, Good, (5 reviews)
"Great place for needed convenience to University of Dayton"
United States
Melissa K.
The price is CA $137
CA $312 total
includes taxes & fees
Sep 2 - Sep 3
The Jackie O ~ One Bedroom Relaxing Retreat

18. New listing Aimi Luxury Retreat, Soft & Cozy

New listing Aimi Luxury Retreat, Soft & Cozy
Downtown Dayton
9.0 out of 10, Wonderful, (10 reviews)
"Exceptionally clean and nicely decorated. "
United States
Sharon M.
The price is CA $163
CA $191 total
includes taxes & fees
Sep 2 - Sep 3
New listing Aimi Luxury Retreat, Soft & Cozy

19. The Big Apple City View with Balcony

The Big Apple City View with Balcony
Walnut Hills
The price is CA $165
CA $310 total
includes taxes & fees
Aug 30 - Aug 31
The Big Apple City View with Balcony

20. Mermaid Tale-Bohemian Bungalow

Mermaid Tale-Bohemian Bungalow
Walnut Hills
6.4 out of 10, (5 reviews)
"Great location near downtown"
United States
Chelsea B.
The price is CA $159
CA $342 total
includes taxes & fees
Sep 9 - Sep 10
Mermaid Tale-Bohemian Bungalow
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Oakwood Hotel Reviews

Find out more about Oakwood

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Oakwood. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Oakwood?

Yes, you can find vacation rentals close to the most popular sights in Oakwood, or you can choose a secluded option if you're looking for a relaxing stay. Oakwood is known for its restaurants and shopping.

What's the top vacation rental that Oakwood has to offer?

Suite Springs: This vacation home rental outside of Oakwood is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware.

What’s there to see and do in Oakwood?

While exploring the area, visit family-friendly sights like Boonshoft Museum of Discovery, or get outside and enjoy nature at Hills & Dales MetroPark. In the larger area, you’ll find University of Dayton and Carillon Historical Park.

What’s a vacation rental in Oakwood like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Oakwood. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for families.