Wayside Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Top Wayside Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Kingsmill Resort
Kingsmill
CA $1,357
per person
Dec 29 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.6/10 Excellent! (1,006 reviews)
We only stayed 1 night and did not really have the chance to utilize the amenities but would love to come back for a longer stay. The condo we stayed in was great and the resort overall looks beautiful.
Reviewed on Oct 12, 2026
Ready to book your vacation to Wayside?
Wayside Hotel Deals
The Jefferson Hotel
101 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
CA $449
CA $522 total
Oct 18 - Oct 19
includes taxes & fees
9.8/10 Exceptional! (1,002 reviews)
"I have never stayed at the Jefferson before, so I was knocked out by the room, the service, and the quality of everything. We had in-suite dining and were highly impressed by both the food and the promptness of delivery. The parking staff, bell hops, and doormen were outstanding. We were mightily ..."
Reviewed on Oct 13, 2026
Graduate by Hilton Richmond
301 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
CA $209
CA $243 total
Oct 28 - Oct 29
includes taxes & fees
Omni Richmond Hotel
100 S 12th St Richmond VA
Fully refundableReserve now, pay when you stay
CA $216
CA $251 total
Nov 1 - Nov 2
includes taxes & fees
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.
What to do in Wayside
Magic Happens at The Wagsters Magic Theatre
CA $47
per adult
Virginia: speakeasy-themed murder mystery dinner at King ́s C
CA $84
per adult
Williamsburg: Echoes of Twilight Late-Night Ghost Tour
CA $35
per adult
100% of travellers recommend
Frequently asked questions
How much does a Wayside vacation package cost?
Offering excellent value package deals from CA $1,108 on Expedia, you'll be pleasantly surprised at how much a vacation to Wayside costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Wayside?
If you're hoping to score a cheap Wayside vacation package, consider planning a trip in January, February and June. You'll typically find better prices on flights and accommodations during these quieter months — ideal for budget-conscious travellers.
How many days is enough for Wayside?
Generally, a handful of days is enough to check out the main sights during your Wayside vacation. However, if you prefer to have more time to kick back or take day tours, consider extending your itinerary.
How to find the best Wayside package deals?
Use Expedia's filters to find some of the best Wayside package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Wayside package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Wayside vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging accommodations and flights separately. Better still, you can personalize your Wayside escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Wayside?
If you're planning a spontaneous Wayside getaway, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Wayside?
- Choose your travel dates: What you want to do in Wayside and your preferred season can help you decide when to get away.
- Budget wisely: Besides the cost of your accommodations, you'll need to consider other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that could crop up during your trip to Wayside.
- Decide how long to go for: Now that you're more familiar with Wayside, you can work out the ideal length of your break. Pull together a draft plan and allocate enough time to cover everything you want to see.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a tailored Wayside vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
