Wayside Vacations from $288

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Your Wayside Vacation

When a city escape is calling your name, answer it with a vacation package to Wayside. With all your travel needs taken care of before you go, all you need to do here is concentrate on having the time of your life. Make your trip to Wayside even more exciting by including some sightseeing. Shirley Plantation, Berkeley Plantation and Historic Westover are among the major attractions you'll want to explore. Don't delay your visit to this city any longer. Your dream Wayside vacation is a few clicks away with Expedia.

The Latest Wayside vacation packages

Price found within the past 48 hours. Click for updated prices.
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $387, price is now $288 per person
$288
per person
Jan 2 - Jan 4
found 4 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Richmond (RIC)
8.8/10 Excellent! (1,294 reviews)
We loved our stay at the Commonwealth Hotel! We were pleasantly surprised with an upgrade to a suite, which was spacious, comfortable, and spotless. The staff were friendly and accommodating throughout our visit. The location was perfect—close to the Carpenter Center and surrounded by excellent restaurants. Overall, a wonderful experience that made our trip even better. Highly recommend!

Reviewed on Nov 12, 2025

A house full of steel balls and games

A house full of steel balls and games

2.5 out of 5
Dumbarton
Price was $539, price is now $403 per person
$403
per person
Dec 24 - Dec 31
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
9.6/10 Exceptional! (97 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

Capitol Inn by Belvilla Richmond Airport VA

Capitol Inn by Belvilla Richmond Airport VA

2.5 out of 5
Price was $483, price is now $363 per person
$363
per person
Dec 24 - Dec 31
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
5.2/10 (55 reviews)
I just love Harry and Mr.Patel Very caring about his customers and very well monitored. Address any issues immediately with thr best professional service.

Reviewed on Sep 5, 2025

Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
Price was $440, price is now $332 per person
$332
per person
Jan 2 - Jan 4
found 4 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Richmond (RIC)
9.2/10 Wonderful! (1,225 reviews)
Wonderful room and beds but it was very hot and we couldn't adjust the temperature (even turned off the heat but still very hot) Parking: not easy, went to the recommended garage, left car and paid via app but I never got confirmation of payment. Got stuck in the garage and had to call the company to have them open the gate...stressful. Coffee could be improved.

Reviewed on Nov 12, 2025

Hilton Richmond Downtown

Hilton Richmond Downtown

4 out of 5
Downtown Richmond
Price was $411, price is now $321 per person
$321
per person
Jan 2 - Jan 4
found 4 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Richmond (RIC)
8.4/10 Very Good! (1,008 reviews)
The food at gather & hem was delicious and open late for when I got back after a concert!! Staff was so attentive and very helpful. Super nice place to stay. Loved the high ceilings in the rooms.

Reviewed on Nov 9, 2025

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Discover the most popular places to visit in Wayside

Small admission for the guided tour, so worth it! 12 generations of the same family in this home and is still a working farm.

Shirley Plantation

You can spend an afternoon browsing the exhibits at Shirley Plantation during your trip to Charles City. While in this family-friendly area, you can savor the top-notch restaurants.

Shirley Plantation

Berkeley Plantation

You can learn about the history of Charles City with a visit to Berkeley Plantation. While in this family-friendly area, you can savor the top-notch restaurants.

Berkeley Plantation

Sherwood Forest Plantation

Learn about the local history of Charles City when you take a trip to Sherwood Forest Plantation. Amble around the area's gardens or visit its shops.

Sherwood Forest Plantation

What to do in Wayside

Williamsburg: The Patriots Historical Walking Tour

Williamsburg: The Patriots Historical Walking Tour

$25
per adult
Williamsburg: The Patriots Historical Walking Tour
Colonial Williamsburg Ghost Stories

Colonial Williamsburg Ghost Stories

$25
per adult
Colonial Williamsburg Ghost Stories
Williamsburg: Pirate Tour

Williamsburg: Pirate Tour

$25
per adult
Williamsburg: Pirate Tour
See all activities in Wayside

Wayside Hotel Deals

Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
301 West Franklin Street, Richmond, VA
Fully refundableReserve now, pay when you stay
$163 nightly
The price is $190 total per night from Nov 19 to Nov 20
$190 total
Nov 19 - Nov 20
Total with taxes and fees
8.4/10 Very Good! (1,393 reviews)
Great location

Reviewed on Nov 8, 2025

Graduate by Hilton Richmond
The Jefferson Hotel

The Jefferson Hotel

5 out of 5
101 West Franklin Street, Richmond, VA
Fully refundableReserve now, pay when you stay
$305 nightly
The price is $355 total per night from Nov 24 to Nov 25
$355 total
Nov 24 - Nov 25
Total with taxes and fees
9.8/10 Exceptional! (1,006 reviews)
Top notch - worth the price!

Reviewed on Nov 11, 2025

The Jefferson Hotel
Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
100 S 12th St, Richmond, VA
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $176 total per night from Nov 23 to Nov 24
$176 total
Nov 23 - Nov 24
Total with taxes and fees
9/10 Wonderful! (1,230 reviews)
The staff was pleasant and professional. We arrived several hours early before check-in and granted

Reviewed on Nov 4, 2025

Omni Richmond Hotel
See all 519 properties in Wayside
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.

Find the Best Wayside Vacation Packages

Wayside Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Richmond Intl. Airport (RIC)
Top Sights
Piney Grove at Southalls Plantation, Evelynton Plantation and Kittiewan Plantation

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Frequently asked questions

How much does a Wayside vacation package cost?
Offering excellent value package deals from $288 on Expedia, you'll be thrilled with how little a vacation to Wayside costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Wayside?
You can typically find lower rates and better availability in November, December and January. Explore our cheap Wayside vacation packages and you could get some great off-season discounts.
How many days is enough for Wayside?
With a well-planned itinerary, you can easily visit the most popular Wayside attractions in a handful of days. But if you prefer to discover lesser-known spots or go on day trips, consider booking your Wayside vacation for longer.
How to find the best Wayside package deals?
Finding a cheap Wayside package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most affordable Wayside package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Wayside vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still have the freedom to create a customized Wayside vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Wayside?
Secure incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Wayside adventure.
Does Expedia offer Book Now, Pay Later Wayside vacation packages?
Your Wayside getaway should be a relaxing escape from your busy life, not a source of money-related stress. So to give you extra flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.