Wayside Vacations from $507

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, 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.

The Latest Wayside vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 out of 5
Price was $903, price is now $507 per person
$507
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
9/10 Wonderful! (3,188 reviews)
The staff was welcoming and polite. The room and amenities were great. The only thing that didn’t work for me was the size of the pillows. They were large but did not give any when you laid on them. They kept my neck at such an awkward angle, I couldn’t sleep on them.

Reviewed on Jan 3, 2026

Hilton Vacation Club Greensprings Williamsburg

Hilton Vacation Club Greensprings Williamsburg

3 out of 5
Price was $902, price is now $508 per person
$508
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
8.4/10 Very Good! (1,004 reviews)
Great property, very pleasant people!

Reviewed on Jan 1, 2026

Williamsburg Lodge, Autograph Collection

Williamsburg Lodge, Autograph Collection

4 out of 5
Colonial Williamsburg
Price was $940, price is now $546 per person
$546
per person
Feb 16 - Feb 20
just found
Roundtrip flight included
New York (JFK) to Richmond (RIC)
9/10 Wonderful! (1,000 reviews)
Staff was very helpful and considerate. Room was fantastic

Reviewed on Jan 2, 2026

Spark by Hilton Williamsburg Historic Area

Spark by Hilton Williamsburg Historic Area

2.5 out of 5
Price was $930, price is now $568 per person
$568
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
8.8/10 Excellent! (64 reviews)
Fresh accommodations will stay again. The breakfast is skimpy running out of milk and black tea bags. Had oatmeal packets (2) one day then none the next. Ended up going outside for breakfast.

Reviewed on Dec 28, 2025

DoubleTree by Hilton Williamsburg

DoubleTree by Hilton Williamsburg

4 out of 5
Price was $965, price is now $603 per person
$603
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
8.4/10 Very Good! (1,001 reviews)
There was not a free breakfast. I don't understand why they charge for parking especially in the off season. The double queen-sized room was small for 2 people. The patio door lock didn't lock. The staff was fantastic!

Reviewed on Dec 31, 2025

Don't see what you're looking for?
See all available trips from Columbus to Wayside
View all trips

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

Picture 11 for Activity Williamsburg: Colonial Ghosts Haunted Walking Tour

Colonial Ghosts: Ghostly Whispers of Williamsburg Ghost Tour

$22
per adult
100% of travellers recommend
Colonial Ghosts: Ghostly Whispers of Williamsburg Ghost Tour
Picture 7 for Activity Williamsburg: Secrets of Williamsburg Walking Tour

Williamsburg: Secrets of Williamsburg Walking Tour

$26
per adult
Williamsburg: Secrets of Williamsburg Walking Tour
History of Slavery Tour in Williamsburg

History of Slavery Tour in Williamsburg

$25
per adult
100% of travellers recommend
History of Slavery Tour in Williamsburg
See all activities in Wayside

Wayside Hotel Deals

The Jefferson Hotel

The Jefferson Hotel

5 out of 5
101 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
$295 nightly
The price is $343 total per night from Jan 11 to Jan 12
$343 total
Jan 11 - Jan 12
Total with taxes and fees
9.8/10 Exceptional! (1,005 reviews)
Quick check-in, clean room, very comfortable bed and pillows

Reviewed on Dec 31, 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
$152 nightly
The price is $177 total per night from Jan 4 to Jan 5
$177 total
Jan 4 - Jan 5
Total with taxes and fees
9/10 Wonderful! (1,299 reviews)
Nice hotel. Clean room, amazing view. Nice staff.

Reviewed on Jan 2, 2026

Omni Richmond Hotel
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
$130 nightly
The price is $152 total per night from Jan 11 to Jan 12
$152 total
Jan 11 - Jan 12
Total with taxes and fees
8.4/10 Very Good! (1,402 reviews)
The staff was wonderful. Chiquita and Khasia in particular were kind and very helpful. All of the staff was attentive. *** The physical property needs some repairs (elevators very slow, halls were poorly painted, the room ceiling and walls were worn).

Reviewed on Dec 30, 2025

Graduate by Hilton Richmond
See all 560 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Wayside vacation package cost?
Offering excellent value package deals from $507 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.