Wayside Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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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.
A house full of steel balls and games

A house full of steel balls and games

2.5 out of 5
Dumbarton
per person
Aug 27 - Sep 2
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
9.6/10 Exceptional! (92 reviews)
Great place to stay. Pete is a great host, easy check in great communication, pinball machines and games in the rooms really great. Quick drive to some good dining.

Reviewed on Jun. 10, 2025

Warner Hall

Warner Hall

3 out of 5
Save 100% on your flight
per person
Sep 15 - Sep 22
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
10/10 Exceptional! (9 reviews)
We had a wonderful, relaxing weekend stay at Warner Hall. The hosts Christina and Fred were very welcoming and the house and property is amazing. The house (more like mansion) and rooms are huge and comfortable with lots of space for reading a book, etc. We really enjoyed the morning coffee and tea service brought straight to our rooms. We felt like royalty! There's so much history to the Warners, we had no idea. Definitely highly recommend this place if you're looking for a break from being busy busy.

Reviewed on Jul. 9, 2025

Barsala At Sphere Apartments

Barsala At Sphere Apartments

3.5 out of 5
per person
Aug 14 - Aug 17
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
8.6/10 Excellent! (14 reviews)
Overall this property was a good place to stay so we could spread out and have extra room for our trip. Communication was fine and checkin instructions were very detailed. I cannot give it 5 stars however. The shower curtain and shower were dirty. There were stains on the bed linens and the comforter as well as a hole in the comforter. The property also charges $5/day for parking which was not disclosed in the original price. The exterior of the property had a dog area and people did not clean up after their dog — this was also the area we were required to park.

Reviewed on Jun. 29, 2025

Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
per person
Aug 14 - Aug 17
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
9.2/10 Wonderful! (1,060 reviews)
The staff was wonderful, but the property is not in great condition, and strong smells of smoke and vape in common areas and hallways.

Reviewed on Jul. 14, 2025

La Quinta Inn & Suites by Wyndham Richmond-Midlothian

La Quinta Inn & Suites by Wyndham Richmond-Midlothian

3 out of 5
North Chesterfield
per person
Aug 27 - Sep 2
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
8.2/10 Very Good! (1,393 reviews)
It was ok. Building could use some updating.

Reviewed on Jul. 13, 2025

Ready to book your vacation to Wayside?

 

Choose your dates

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
The price is CA $218 per night from Jul 27 to Jul 28
CA $218
CA $253 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (1,144 reviews)
"Front desk staff was friendly. Room was clean and quiet. Restaurant downstairs had great breakfast."

Reviewed on Jul. 13, 2025

Omni Richmond 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 $91 per night from Aug 3 to Aug 4
CA $91
CA $106 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (138 reviews)
"New property with very clean. Rooms are specious and beautiful. Only thing is that it is little away from shopping."

Reviewed on Jul. 11, 2025

Studio 6 Richmond, VA - Airport
The Commonwealth
The Commonwealth
4 out of 5
901 Bank St, Richmond, VA
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Jul 27 to Jul 28
CA $193
CA $225 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (1,250 reviews)
"The room was very spacious and beautiful. I wish there was an outdoor area to sit and enjoy the beautiful scenery, however, there are outdoor patios within walking distance, which made our stay very enjoyable. Will definitely be back."

Reviewed on Jul. 10, 2025

The Commonwealth
See all 523 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

A Virginia landmark for Berkeley Plantation.

Private tour from Williamsburg to Berkeley Plantation

CA $405
per adult
Private tour from Williamsburg to Berkeley Plantation
Full-Day Tour in Washington DC

Full-Day Tour in Washington DC

CA $172
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
Colonial Williamsburg: Colonial History Guided Walking Tour
See all activities in Wayside

Frequently asked questions

How much does a Wayside vacation package cost?
Offering excellent value package deals from CA $866 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.