Wayside Vacations from $300

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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.
Virginia Crossings Hotel, Tapestry Collection by Hilton

Virginia Crossings Hotel, Tapestry Collection by Hilton

3.5 out of 5
Price was $415, price is now $300 per person
$300
per person
Nov 3 - Nov 6
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (1,000 reviews)
Great staff, beautiful grounds, awesome running trail!

Reviewed on Sep 23, 2025

Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Downtown Richmond
Save 100% on your flight
Price was $574, price is now $370 per person
$370
per person
Nov 3 - Nov 6
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.4/10 Very Good! (1,347 reviews)
Nice rooftop bar/ restaurant

Reviewed on Sep 21, 2025

Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
Price was $490, price is now $346 per person
$346
per person
Nov 3 - Nov 6
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
9.2/10 Wonderful! (1,189 reviews)
The room was comfortable and clean. The staff was pleasant and the resident cat so friendly.

Reviewed on Sep 24, 2025

Hilton Richmond Hotel & Spa/Short Pump

Hilton Richmond Hotel & Spa/Short Pump

4 out of 5
Short Pump
Price was $556, price is now $405 per person
$405
per person
Nov 3 - Nov 6
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (1,006 reviews)
From the moment I entered, the staff was very polite and respectful. The hotel was very clean. My room was comfortable and cleaned daily.

Reviewed on Sep 20, 2025

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $542, price is now $399 per person
$399
per person
Nov 3 - Nov 6
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (1,278 reviews)
The Commonwealth has an unbeatable location in downtown Richmond — you can walk to the Capitol, great restaurants, and plenty of sights. Check-in was smooth and staff were friendly, but outside of that they often seemed disengaged, spending time on their phones instead of checking on guests. Rooms are clean and comfortable, and the hotel itself has plenty of character. With more consistent attentiveness, it would be an excellent stay.

Reviewed on Sep 25, 2025

Don't see what you're looking for?
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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

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

Piney Grove at Southalls Plantation

Learn about the local history of Charles City when you take a trip to Piney Grove at Southalls Plantation. Amble around this family-friendly area's gardens, or seek out the golf courses.

Piney Grove at Southalls Plantation

What to do in Wayside

Get ready to travel back in time as our tours transport you to pivotal moments in history.

Colonial Ghosts Ultimate Dead of Night Haunted Ghost Tour

$33
per adult
94% of travellers recommend
Colonial Ghosts Ultimate Dead of Night Haunted Ghost Tour
Colonial Williamsburg: Colonial History Guided Walking Tour

Colonial Williamsburg: Colonial History Guided Walking Tour

$25
per adult
100% of travellers recommend
Colonial Williamsburg: Colonial History Guided Walking Tour
Full-Day Tour in Washington DC

Full-Day Tour in Washington DC

$125
per adult
Full-Day Tour in Washington DC
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
$152 nightly
The price is $177 total per night from Oct 12 to Oct 13
$177 total
Oct 12 - Oct 13
Total with taxes and fees
8.2/10 Very Good! (1,356 reviews)
"Nice rooftop bar/ restaurant"

Reviewed on Sep 21, 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 Oct 5 to Oct 6
$355 total
Oct 5 - Oct 6
Total with taxes and fees
9.8/10 Exceptional! (1,031 reviews)
"Hotel was wonderful. Staff was outstanding and willing to help with any need."

Reviewed on Sep 24, 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
$159 nightly
The price is $185 total per night from Oct 12 to Oct 13
$185 total
Oct 12 - Oct 13
Total with taxes and fees
9/10 Wonderful! (1,198 reviews)
"Clean room great staff"

Reviewed on Sep 22, 2025

Omni Richmond Hotel
See all 512 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.

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Frequently asked questions

How much does a Wayside vacation package cost?
Offering excellent value package deals from $300 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.