Waynesboro Vacations from $667
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Your Waynesboro Vacation
Say farewell to planning hassles and hello to a Waynesboro vacation package. With your travel details organized before you leave, you can focus on discovering every inch of this city, starting with Chestnut Springs, which is great for adventure sports, skiing and walking. If your trip to Waynesboro includes a little sightseeing, take in renowned attractions like Veritas Vineyard and Winery, Afton Mountain Vineyards and Swannanoa Palace. Browse Expedia's extensive range of travel options and start planning your ultimate vacation to Waynesboro now.
The Latest Waynesboro vacation packages
Price found within the past 48 hours. Click for updated prices.
Cave Hill Farm Bed & Breakfast
$667
per person
Nov 5 - Nov 8
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Weyers Cave (SHD)
9.4/10 Exceptional! (358 reviews)
The staff was awesome, the house was super beautiful and historic and the surrounding area was also very cool! About a 25 minute drive from the bottom of Shenandoah which was super convenient and right by a few restaurants and the Cave Hill Brewery (which was also so awesome)!! Will definitely be recommending to others, such a cool, unique experience
Reviewed on Sep 11, 2026
Massanutten's Woodstone Meadows by Tripforth
$705
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Weyers Cave (SHD)
8.8/10 Excellent! (231 reviews)
This was our first time at Massanutten Resort, and we loved it!! It's perfect for families, with plenty to do. We would definitely come back again!
Reviewed on Sep 7, 2026
Iris Inn and Cabins
$1,142
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Weyers Cave (SHD)
9.8/10 Exceptional! (15 reviews)
From the minute you step out of your car you are greeted with an insane moment of “wow”. Right in front of the hotel is a beautiful scenery from up top overlooking the area. You feel like you are in a different world. Then after walking in, we are greeted with kind faces who wonderfully explain your stay. Now lets talk about the room. Been to plenty of hotels in my life and this one is by far the most inviting and comforting. With plans ahead the following days my wife and I had trouble getting up due to the comfort! lol i couldn’t recommend this hotel enough. Oh and by the way, grab a bite for dinner there as well, you wont be disappointed.
Reviewed on Sep 24, 2026
Stay near popular Waynesboro attractions
Rockfish Gap Entrance Shenandoah
9.0/10 (233 reviews)
Gateway to Shenandoah National Park, this entrance station marks the southern starting point of the scenic Skyline Drive. Rangers provide maps and local insights before you embark on your Blue Ridge Mountains adventure.
Basic City Beer Co.
9.2/10 (10 reviews)
Basic City Beer Co. crafts innovative beers with pure artesian spring water in a historic industrial building. Savor wood-fired pizzas while enjoying arcade games, pool tables, and live music in this vibrant brewery.
Wayne Theatre
8.0/10 (13 reviews)
This historic 1926 vaudeville house offers intimate performances with exceptional acoustics in the heart of Waynesboro. Enjoy theater, concerts, or browse the art gallery before settling in for an evening show.
Zeus Digital Theater
8.6/10 (18 reviews)
This modern cinema complex offers eight screens with digital projection and 3D capabilities in Waynesboro. Enjoy the spacious seating and arcade area while catching the latest first-run movies.
Shenandoah Valley Art Center
9.0/10 (17 reviews)
This vibrant cultural hub showcases rotating exhibits from local Shenandoah Valley artists across three galleries. Visit during the Virginia Fall Foliage Art Show in October to experience the region's creative spirit.
Waynesboro Heritage Museum
7.8/10 (8 reviews)
Housed in a renovated 1908 bank building, this museum chronicles Waynesboro's evolution from the 1700s through the 20th century. Explore the original bank vault while discovering the city's industrial heritage.
P. Buckley Moss Gallery
8.0/10 (10 reviews)
The P. Buckley Moss Gallery showcases the artist's distinctive watercolors inspired by Shenandoah Valley landscapes. Browse original paintings and prints in a serene setting with knowledgeable, pressure-free staff.
Hermitage Hill Farm & Stables
8.4/10 (6 reviews)
This working horse farm doubles as Stable Craft Brewing, offering a rustic yet elegant countryside setting. Sample craft beers in the air-conditioned hall or attend seasonal events amid the equestrian atmosphere.
What to do in Waynesboro
Blue Ridge Parkway Virginia Self-Guided Audio Tour
$13
per traveler
Waynesboro Hotel Deals
Holiday Inn Express & Suites Waynesboro East by IHG
108 Chicurel Lane Waynesboro VA
Fully refundable
$115 nightly
$128 total
Sep 30 - Oct 1
Total with taxes and fees
Quality Inn Waynesboro - Skyline Drive
640 W Broad St Waynesboro VA
Fully refundable
$72 nightly
$80 total
Sep 29 - Sep 30
Total with taxes and fees
7/10 Good! (888 reviews)
"Amongst the 17 hotels on our major road trip this ranked highly. It was - for our overnight stop - perfect"
Reviewed on Sep 25, 2026
Grey Pine Lodge
494 Three Notched Mountain Hwy Waynesboro VA
Fully refundableReserve now, pay when you stay
$113 nightly
$126 total
Sep 30 - Oct 1
Total with taxes and fees
9.6/10 Exceptional! (11 reviews)
"Love this place !"
Reviewed on Sep 24, 2026
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 Waynesboro Vacation Packages
Waynesboro Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Charlottesville-Albemarle Airport (CHO) |
Population | 21,500 |
Max Temp Winter | 45ºF |
Max Temp Summer | 85ºF |
Top Sights | American Shakespeare Center, Ravens Roost Overlook and Wayne Theatre |
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Frequently asked questions
How much does a Waynesboro vacation package cost?
You'll find cheap prices from $667 on Expedia for your Waynesboro escape. However, a range of factors like the season, choice of hotel and length of stay will determine how much your vacation to Waynesboro costs.
What are the cheapest months to go to Waynesboro?
You're likely to find lower rates and greater availability in June, July and December. Check out our cheap Waynesboro vacation packages and you could land some great off-season deals.
How many days is enough for Waynesboro?
With a well-planned itinerary, you can easily tick off the top Waynesboro attractions in a handful of days. But if you'd like to discover hidden spots or go on day trips, think about booking your Waynesboro vacation for longer.
Is it worth booking a vacation package to Waynesboro?
It's easy to see why a Waynesboro vacation is on the to-do list of many travelers. Well-known attractions like Zeus Digital Theater are just the beginning of things to keep you busy here.
How to find the best Waynesboro package deals?
Use Expedia's filter tool to help you find some of the best Waynesboro package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Waynesboro package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Waynesboro vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and stays separately. Better still, you can customize your Waynesboro trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Waynesboro?
If you have your Waynesboro travel dates finalized, book as soon as you can to snap up some unbeatable deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are great for traveling on a whim.
How to plan a trip to Waynesboro?
- Pick your dates: The things you plan to do in Waynesboro and your favorite season will help you decide when to go.
- Plan your budget wisely: In addition to the cost of your stay, you should consider other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that may arise during your trip to Waynesboro.
- Organize your Waynesboro escape with Expedia's trip planning tool: Look for and book hotels and experiences all in one place. You can also collaborate with your group to plan an unforgettable trip to Waynesboro together.
- Decide how long to go away for: Now that you're up to speed on Waynesboro, you can figure out the perfect length of your vacation. Put together a draft itinerary and allocate enough time to cover everything you want to see.
- Combine your airfare and accommodations: Once you've nailed down your dates and duration, lock in the right Waynesboro vacation package for you.
- Add on experiences and excursions: Take a look at our travel guide to find some fun things to do in Waynesboro in Waynesboro. Book tickets or make reservations before you go to save time and avoid the hassle of looking for activities when you arrive.
Does Expedia offer Book Now, Pay Later Waynesboro vacation packages?
Set off on your dream getaway to Waynesboro with help from Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait until your next paycheck — we've partnered with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans let you split the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stay on budget and snag great deals before they sell out.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
