Wayside Vacation Packages

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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.

Top Wayside Vacation Deals

Price found within the past 48 hours. Click for updated prices.
King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

4 out of 5
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Richmond (RIC)
8.6/10 Excellent! (74 reviews)
Super close to Water Country USA. Ants were a slight problem but that’s the season we are in. Everyone was really nice at the property. Kitchen/living room was very small in the 1 bedroom when the sleeper sofa was pulled out.

Reviewed on Jul. 11, 2025

Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
per person
Sep 27 - Oct 4
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,004 reviews)
It was great! We look forward to staying again. Thank you!

Reviewed on Aug. 12, 2025

Wedmore Place

Wedmore Place

3.5 out of 5
per person
Sep 27 - Oct 4
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.6/10 Exceptional! (1,000 reviews)
This place is so wonderfully unique with all of the antique furniture and layout of the building! Although unused due to the season, there was a fireplace in the bedroom. We enjoyed our lunch in the courtyard beside the fountain. We had a wine tasting experience, and an evening swim in the beautiful outdoor pool. I would definitely come back here again!

Reviewed on Aug. 13, 2025

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Richmond (RIC)
8.8/10 Excellent! (1,001 reviews)
A very nice place family oriented to relax.

Reviewed on Aug. 11, 2025

Patriots Inn

Patriots Inn

2.5 out of 5
per person
Sep 27 - Oct 4
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.4/10 Exceptional! (844 reviews)
For what I paid, the room was very large and comfortable. Unfortunately, the bed was very uncomfortable for me. Lumpy and soft.

Reviewed on Aug. 12, 2025

Ready to book your vacation to Wayside?

 

Choose your dates

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
The price is CA $392 per night from Aug 24 to Aug 25
CA $392
CA $456 total
Aug 24 - Aug 25
includes taxes & fees
9.8/10 Exceptional! (1,009 reviews)
"Concierge and transportation staff were nothing short of amazing."

Reviewed on Aug. 12, 2025

The Jefferson Hotel
Studio 6 Richmond, VA - Airport

Studio 6 Richmond, VA - Airport

2 out of 5
580 Trampton Road, Sandston, VA
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Sep 1 to Sep 2
CA $105
CA $122 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (210 reviews)
"1"

Reviewed on Aug. 10, 2025

Studio 6 Richmond, VA - Airport
Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
100 S 12th St, Richmond, VA
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Aug 24 to Aug 25
CA $208
CA $242 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,163 reviews)
"Nice"

Reviewed on Aug. 12, 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Wayside

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

Evelynton Plantation

You can spend an afternoon exploring the galleries in Evelynton Plantation in Charles City. While in this family-friendly area, you can savor the top-notch restaurants.

Evelynton Plantation

What to do in Wayside

Full-Day Tour in Washington DC

Full-Day Tour in Washington DC

CA $171
per adult
Full-Day Tour in Washington DC
Colonial Williamsburg: Colonial History Guided Walking Tour

Colonial Williamsburg: Colonial History Guided Walking Tour

CA $34
per adult
100% of travellers recommend
Colonial Williamsburg: Colonial History Guided Walking Tour
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

CA $37
per adult
90% of travellers recommend
Colonial Ghosts Ultimate Dead of Night Haunted Ghost Tour
See all activities in Wayside

Frequently asked questions

How much does a Wayside vacation package cost?
Offering excellent value package deals from CA $1,068 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?

  1. Choose your travel dates: What you want to do in Wayside and your preferred season can help you decide when to get away.
  2. 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.
  3. 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.
  4. 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.