Oakwood Vacations from $307

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Your Oakwood Vacation

Reserving a tailor-made Oakwood vacation package is a wonderful way to become acquainted with this unique neighborhood. From its renowned sites to its lesser-known delights, you won't be short of new adventures. Your trip to Oakwood wouldn't be complete without seeing big-name attractions nearby such as Edgar Allan Poe Museum, Virginia State Capitol and White House of the Confederacy. Whatever your travel goals or the size of your budget, booking a perfect Oakwood vacation is simple with Expedia.

The Latest Oakwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
A house full of steel balls and games

A house full of steel balls and games

2.5 out of 5
Dumbarton
Price was $451, price is now $307 per person
$307
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
19.2/10 Exceptional! (99 reviews)
The room is amazing! The bed is more comfortable than my own at home! Host is amazing! Amazing games and a great space! I Can't wait to recommend to friends!

Reviewed on Nov 8, 2025

Holiday Inn Club Vacations Williamsburg Resort by IHG

Holiday Inn Club Vacations Williamsburg Resort by IHG

3.5 out of 5
Save 100% on your flight
Price was $515, price is now $340 per person
$340
per person
Jan 25 - Jan 31
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
18/10 Exceptional! (525 reviews)
The set up was comfortable, clean and efficient.

Reviewed on Nov 18, 2025

Hilton Richmond Hotel & Spa/Short Pump

Hilton Richmond Hotel & Spa/Short Pump

4 out of 5
Short Pump
Save 100% on your flight
Price was $587, price is now $424 per person
$424
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
17.6/10 Exceptional! (1,002 reviews)
The room was clean. The sheets had an unpleasant smell. The maintenance should check the outlet in the bathroom as hair dryer and curler kept falling out of the socket. Gaps around shower door allowed water to escape. The front desk emplyee was very nice as were the restaurant staff.

Reviewed on Nov 14, 2025

Hyatt Select Richmond/Chester

Hyatt Select Richmond/Chester

3 out of 5
Price was $519, price is now $380 per person
$380
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
16.4/10 Exceptional! (1,000 reviews)
Everything very professional and clean best hotel around the area

Reviewed on Nov 20, 2025

Hilton Richmond Downtown

Hilton Richmond Downtown

4 out of 5
Downtown Richmond
Save 100% on your flight
Price was $878, price is now $647 per person
$647
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
16.8/10 Exceptional! (1,004 reviews)
Everything was very nice!

Reviewed on Nov 17, 2025

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Where to stay in Oakwood

Find the best Oakwood areas and neighborhoods for the activities you enjoy most. Learn more about Oakwood
Virginia featuring a sunset

Downtown Richmond

2 out of top 10 points of interest in this area
4/5(1,138 area reviews)

Explore the central business district, home to Fortune 500 companies and architectural gems like the Virginia State Capitol. Discover vibrant nightlife in Shockoe Bottom and Shockoe Slip districts.

Find hotels in Downtown Richmond
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Oakwood

Virginia Commonwealth University

Virginia Commonwealth University

4.5/5(414 reviews)

Explore the campus of Virginia Commonwealth University during your stay in Richmond. Stroll along the area's riverfront or experience its great live music.

Virginia Commonwealth University
Richmond

Broad Street

4/5(681 reviews)

During your trip to Richmond, you can find the perfect gifts to bring home at Broad Street. While you're here, you can savor the top-notch restaurants.

Broad Street
Altria Theater

Altria Theater

4.5/5(79 reviews)

Enjoy a performance at Altria Theater, a storied theater in Richmond. Amble around the area's picturesque gardens or attend a sporting event.

Altria Theater

Things to do

Historic Trolley Tour

Historic Trolley Tour

$42
per adult
100% of travellers recommend
Historic Trolley Tour
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

$35
per adult
100% of travellers recommend
Richmond: Guided Hike in James River Park
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.