Wayside Vacations from $452
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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.
Linden Row Inn
Downtown Richmond
$527
per person
Nov 2 - Nov 5
found 23 hours ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
9.2/10 Wonderful! (1,439 reviews)
I’ve been to Richmond several times because I love the area. I’ve stayed at different hotels, and I wanted to try this one because it had pretty good reviews and nice pictures. However, I have mixed feelings about this property.
We arrived at the hotel around 2:00 PM, and check-in was at 3:00 PM. Since I have VIP status with Expedia, I thought I might be able to check in early. I asked the staff member at the front desk, who was by himself at the time, and he simply told me, “No, I don’t have a room for you yet.” I left right away and didn’t bother mentioning my VIP status. I didn’t like how cold the interaction felt, although I understand that he was just following the hotel’s 3:00 PM check-in policy.
We came back at almost 4:00 PM, and there was a different staff member at the front desk. He was completely different—very pleasant and welcoming. He even accompanied us to the room and helped us find it. That pretty much sums up my experience with the staff during my stay: mixed. The first staff member was cold and unwelcoming, while the second was friendly, helpful, and pleasant.
The room itself was very dated, but it was clean. The bed was quite high, but I liked that it was firm. The AC, however, was extremely annoying. About every 10 minutes, I would wake up because of the noise it made whenever it automatically turned on.
The location is good, but the surrounding area is a little boring. There aren’t many good restaurants within walking distance.
Overall, I don’t thi
Reviewed on Aug 15, 2026
Williamsburg Inn, an official Colonial Williamsburg Hotel
Colonial Williamsburg
$1,144
per person
Oct 18 - Oct 21
found 2 hours ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
9.8/10 Exceptional! (390 reviews)
Great days with our family. Wonderfull rooms. Very helpful snd super friendly staff
The restaurant is ok. The hotel is superb!!
Reviewed on Aug 11, 2026
What to do in Wayside
Masquerade Murder Mystery Dinner Show at Corey's
$60
per adult
Wayside Hotel Deals
The Jefferson Hotel
101 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
$295 nightly
$343 total
Sep 7 - Sep 8
Total with taxes and fees
Omni Richmond Hotel
100 S 12th St Richmond VA
Fully refundableReserve now, pay when you stay
$199 nightly
$231 total
Aug 16 - Aug 17
Total with taxes and fees
9/10 Wonderful! (1,527 reviews)
"Omni Hotel is top notch, this was our first time staying at an Omni Hotel and we loved it. It was clean, the staff was awesome, they provided us with great places to visit, and eat. And I cant say enough about the bed....it was the most comfortable bed we've slept in away from home. We've stayed ..."
Reviewed on Aug 13, 2026
Graduate by Hilton Richmond
301 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
$139 nightly
$161 total
Aug 23 - Aug 24
Total with taxes and fees
8.4/10 Very Good! (1,424 reviews)
"very convenient"
Reviewed on Aug 15, 2026
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 $452 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.
