Oakwood Holidays

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Your Oakwood Holiday

Our Oakwood holiday packages are a time-saving and convenient way to organise and reserve your next retreat. Experience the magic of this unique neighbourhood without the hassle of having to organise everything yourself. Can't wait to get out and see the sights during your trip to Oakwood? Be sure to stop by nearby attractions such as Edgar Allan Poe Museum, Black History Museum and White House of the Confederacy. Whatever your ideal Oakwood holiday looks like, you can turn it into reality with Expedia.

Where to stay in Oakwood

Find the best Oakwood areas and neighborhoods for the activities you enjoy most. Learn more about Oakwood
A city skyline at dusk with illuminated buildings, a river, and a bridge.

Downtown Richmond

3 out of top 10 points of interest in this area

Downtown Richmond is popular for its abundant dining options, and if you're looking for more to see and do, you might think about a trip to Canal Walk or Virginia State Capitol.

Find hotels in Downtown Richmond
A bridge over a river with multiple arches, surrounded by trees and a railway track.

Short Pump

1 out of top 10 points of interest in this area

Short Pump is popular for its ample dining options, and you might make a stop by Short Pump Town Center, a top place to visit in the area.

Find hotels in Short Pump
A cityscape with a sunset, featuring a mix of historic and modern buildings, a prominent dome structure, and a wide street layout.

Fan District

You'll enjoy the live music and monuments in Fan District. You might want to make time for a stop at Monument Avenue or Jefferson Davis Monument.

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A cityscape with a prominent white building with columns, surrounded by lush green lawns and trees, under a partly cloudy sky.

North Chesterfield

While North Chesterfield isn't home to many top sights, Chesterfield Towne Center and River City Sportsplex are some notable places to visit nearby.

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A building with a tower, a sign reading "Greater Richmond Convention Center," and a street intersection with traffic lights.

Richmond City Center

While visiting Richmond City Center, you might make a stop by sights like Broad Street and Richmond CenterStage.

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Top hotels in Oakwood

The Jefferson Hotel

The Jefferson Hotel

101 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
£249
23 Aug - 24 Aug
includes taxes & fees
9.8/10 Exceptional! (1,003 reviews)
"The room was clean and the bed was very comfortable. The staff were very attentive and friendly. We had wonderful breakfasts delivered to our room each morning. Valet parking service was excellent. The shuttle service was also excellent."

Reviewed on 6 Aug 2026

The Jefferson Hotel
Omni Richmond Hotel

Omni Richmond Hotel

100 S 12th St Richmond VA
Fully refundableReserve now, pay when you stay
£131
9 Aug - 10 Aug
includes taxes & fees
Omni Richmond Hotel
Graduate by Hilton Richmond

Graduate by Hilton Richmond

301 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
£119
16 Aug - 17 Aug
includes taxes & fees
Graduate by Hilton Richmond
See all 998 properties in Oakwood
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays
Golf Holidays
Golf Holidays
Luxury Holidays
Luxury Holidays
gay friendly holidays
LGBTQ+ Holidays
LGBTQ+ Holidays
Romantic Holidays
Romantic Holidays
Ski Holidays
Ski Holidays
Pet Friendly Holidays
Pet Friendly Holidays
Holiday in Month
Where to go when
Where to go when

Frequently asked questions

How do I get a cheap travel package to Oakwood?
Booking a hotel and flight together with Expedia won't just save valuable time — it'll save you a nice amount too. An Oakwood travel package makes it a cinch to arrange your perfect trip. With more than 550 airlines across the world to pick from, finding flights that suit your busy schedule won't be a problem. Not only that, we've got over 1,000,000 properties globally to select from. Now that's what you call choice. No matter who you are, Expedia puts the world within your reach.

Things to do

Historic Trolley Tour

Historic Trolley Tour

£34
per adult
100% of travellers recommend
Historic Trolley Tour
Down in the Shokoe Bottom, the most haunted neighborhood with 350+ years of history and hauntings!

The Haunted History of Richmond tour

£23
per adult
The Haunted History of Richmond tour
Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour

Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour

£8
per traveller
80% of travellers recommend
Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour
See all activities in Richmond

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.