Wayside Vacations from $555

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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.
Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

3.5 out of 5
Price was $759, price is now $555 per person
$555
per person
Apr 25 - May 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
9.4/10 Exceptional! (327 reviews)
Spacious, clean, except under the night tables beside the bed.

Reviewed on Jan 13, 2026

Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Save 100% on your flight
Price was $1,130, price is now $748 per person
$748
per person
Apr 25 - May 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
8.8/10 Excellent! (791 reviews)
I can’t say enough good things about this hotel. Our room was clean, large, beds comfortable, bathroom and two sink areas were convenient. The deck was overlooking a pond and a nice place to relax after walking the restoration area. Being close to the hotel and restaurants was perfect. And, the staff were exceptional.

Reviewed on Mar 8, 2026

Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

3 out of 5
Price was $781, price is now $570 per person
$570
per person
Apr 25 - May 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
8.8/10 Excellent! (439 reviews)
Staff was very helpful and friendly. The room was very clean and comfortable. My kids loved the game room and pool! We would absolutely stay here again.

Reviewed on Feb 8, 2026

Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Downtown Richmond
Save 100% on your flight
Price was $994, price is now $748 per person
$748
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.4/10 Very Good! (1,373 reviews)
Staff was warm and friendly - worst bed I've ever slept in though

Reviewed on Mar 12, 2026

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Save 100% on your flight
Price was $1,268, price is now $961 per person
$961
per person
Apr 25 - May 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
8.8/10 Excellent! (1,007 reviews)
I really enjoyed my stay; the customer service was excellent and I will definitely stay there again.

Reviewed on Mar 6, 2026

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The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
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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
Richmond_BerkeleyPlantation_553248621532661619_13

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: Colonial Ghosts Haunted Pub Crawl

Williamsburg: Colonial Ghosts Haunted Pub Crawl

$30
per adult
Williamsburg: Colonial Ghosts Haunted Pub Crawl
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

$35
per adult
Williamsburg: Secrets of Williamsburg Walking Tour
See all activities in Wayside

Wayside Hotel Deals

Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
100 S 12th St Richmond VA
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $190 total per night from Mar 15 to Mar 16
$190 total
Mar 15 - Mar 16
Total with taxes and fees
9/10 Wonderful! (1,333 reviews)
The Omni Richmond Hotel is a well-located downtown hotel known for its convenient access to restaurants, historic sites, and the Shockoe Slip area. The rooms are generally comfortable

Reviewed on Mar 12, 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
$147 nightly
The price is $171 total per night from Mar 22 to Mar 23
$171 total
Mar 22 - Mar 23
Total with taxes and fees
8.4/10 Very Good! (1,343 reviews)
Terrible

Reviewed on Mar 12, 2026

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
$315 nightly
The price is $366 total per night from Mar 15 to Mar 16
$366 total
Mar 15 - Mar 16
Total with taxes and fees
9.8/10 Exceptional! (1,008 reviews)
1) Dodgy area. not sure I would walk the area at night. View from my room looked out on a graffiti covered building across a parking lot. Be prepared for ambulances and sirens blasting at least 2 or 3 times during the night. 2) rooms are all different, but my room was...less than optimal. The bed ...

Reviewed on Mar 9, 2026

The Jefferson Hotel
See all 597 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 $555 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.