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

Oakwood Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Oakwood vacation rentals

Smart TV, books

1. 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, (118 reviews)
"Great place. Clean, in great shape and close to UD!!"
United States
Paul B.
The price is ￥12,621
￥19,720 total
includes taxes & fees
Aug 11 - Aug 12
Updated Historical apartment close to a park and two blocks from the best dining
Smart TV

2. Historic Oregon District

Historic Oregon District
Downtown Dayton
9.8 out of 10, Exceptional, (82 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 ￥12,621
￥19,720 total
includes taxes & fees
Aug 17 - Aug 18
Historic Oregon District
Iron/ironing board, WiFi, bed sheets

3. Oregon District I Free Parking I Getaway

Oregon District I Free Parking I Getaway
Downtown Dayton
9.2 out of 10, Wonderful, (17 reviews)
"Very beautiful location with lots of walkable restaurants."
United States
Daniel Moorman
The price is ￥12,305
￥26,503 total
includes taxes & fees
Aug 10 - Aug 11
Oregon District I Free Parking I Getaway
Living area

4. 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 ￥10,885
￥26,819 total
includes taxes & fees
Aug 18 - Aug 19
The Castro
Exterior

5. 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 ￥14,001
￥28,988 total
includes taxes & fees
Aug 10 - Aug 11
Cozy Historic Home | Historic Oregon District
Smart TV, fireplace, books

6. Oasis On Oak 2-bedroom house in Historic Downtown Dayton for Perfect Living!

Oasis On Oak 2-bedroom house in Historic Downtown Dayton for Perfect Living!
South Park
10.0 out of 10, Exceptional, (17 reviews)
"Everything was great!"
United States
Corey K.
The price is ￥14,056
￥35,147 total
includes taxes & fees
Aug 11 - Aug 12
Oasis On Oak 2-bedroom house in Historic Downtown Dayton for Perfect Living!
Interior

7. Gem City Haven

Gem City Haven
Linden Heights
9.2 out of 10, Wonderful, (15 reviews)
"The house was very clean and local to the attractions we needed for the weekend "
United States
Kirsten R.
The price is ￥13,725
￥24,768 total
includes taxes & fees
Aug 25 - Aug 26
Gem City Haven
Exterior

8. Walk to Dining & Attractions | Free Coffee

Walk to Dining & Attractions | Free Coffee
Downtown Dayton
9.0 out of 10, Wonderful, (4 reviews)
"Loved the Oregon district. Can walk to many shops and restaurants. "
United States
vince H.
The price is ￥12,621
￥26,031 total
includes taxes & fees
Aug 11 - Aug 12
Walk to Dining & Attractions | Free Coffee
TV

9. Cozy apartment #1

Cozy apartment #1
North Riverdale
9.6 out of 10, Exceptional, (4 reviews)
"The apartment was super nice inside! It was well kept and the host is very well at communicating! Would stay here again:)"
United States
Hailey
The price is ￥7,951
￥24,516 total
includes taxes & fees
Sep 8 - Sep 9
Cozy apartment #1
Interior

10. 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 ￥16,044
￥40,970 total
includes taxes & fees
Aug 20 - Aug 21
Cozy, Renovated 3-Bedroom in the Heart of Dayton
Interior

11. 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 ￥15,192
￥33,492 total
includes taxes & fees
Aug 13 - Aug 14
Twinkle, twitch and stay awhile/ Bewitched Inspired 2 bedroom apartment
1 bedroom, iron/ironing board, WiFi, bed sheets

12. 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 ￥13,567
￥27,292 total
includes taxes & fees
Aug 30 - Aug 31
Ruby Red Haven – Chic Downtown Retreat Dayton
Private kitchen

13. 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 ￥15,618
￥35,406 total
includes taxes & fees
Aug 10 - Aug 11
The Jackie O ~ One Bedroom Relaxing Retreat
2 bedrooms, WiFi, bed sheets

14. 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 ￥18,142
￥39,178 total
includes taxes & fees
Aug 10 - Aug 11
Historical Louisiana Style Home
Exterior

15. 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 ￥15,618
￥32,341 total
includes taxes & fees
Aug 25 - Aug 26
Boho loft is a fabulous 2-bedroom apartment close to downtown
TV

16. Prime Location I Mins to Dining I Downtown Dayton

Prime Location I Mins to Dining I Downtown Dayton
Downtown Dayton
The price is ￥13,252
￥28,239 total
includes taxes & fees
Aug 10 - Aug 11
Prime Location I Mins to Dining I Downtown Dayton
Interior

17. Cowboy Cottage country charm in the city

Cowboy Cottage country charm in the city
Walnut Hills
6.0 out of 10, (11 reviews)
"The cottage was adorable and so cozy! Perfect for our week stay. The host was communicative and very friendly. "
United States
Ashley W.
The price is ￥12,463
￥28,712 total
includes taxes & fees
Aug 16 - Aug 17
Cowboy Cottage country charm in the city
Exterior

18. Steps away from Dayton’s Historic Oregon District

Steps away from Dayton’s Historic Oregon District
Downtown Dayton
10.0 out of 10, Exceptional, (3 reviews)
"Very cool historic neighborhood! Awesome restaurants in walking distance!"
United States
James c.
The price is ￥16,959
￥32,104 total
includes taxes & fees
Aug 17 - Aug 18
Steps away from Dayton’s Historic Oregon District
Terrace/patio

19. The Big Apple City View with Balcony

The Big Apple City View with Balcony
Walnut Hills
The price is ￥18,773
￥35,180 total
includes taxes & fees
Aug 10 - Aug 11
The Big Apple City View with Balcony
TV

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 ￥18,142
￥39,223 total
includes taxes & fees
Aug 10 - Aug 11
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.
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Top Oakwood Hotel Reviews

Drury Inn & Suites Middletown Franklin

Drury Inn & Suites Middletown Franklin

8/10 Good
"Every single staff member was very friendly and personable. The staff who worked breakfast, pool, bar tender, front desk, maintenance. Everyone was kind and helpful."
Jeannie 1-night trip
Posted 1 hour ago
Drury Inn & Suites Middletown Franklin

Find out more about Oakwood

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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?

4BR Home - Airport- UD - WPAFB - POOL -Sleeps 7: This vacation home rental outside of Oakwood offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a patio and a selection of games.

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 National Museum of the United States Air Force.

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.