
Waynesboro Vacations from $392
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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.

Days Inn by Wyndham Waynesboro
Price was $445, price is now $392 per person
$392
per person
Oct 2 - Oct 5
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Weyers Cave (SHD)
7.2/10 Good! (1,003 reviews)
This hotel was decent for the price and worked well for an overnight stay. Check-in was quick, and the staff was friendly. The beds were comfortable, the air conditioning worked well, and we slept great without any noticeable outside noise.
The room had been cleaned, but only minimally. There was dirt behind the chairs, the top of the toilet seat needed cleaning, and there were a few small stains on the linens. We did not see any bugs or mold, though. We also did not try the breakfast.
Overall, the property felt lower quality than the typical Days Inn or Wyndham property, but it was acceptable for the price we paid. I would stay again at a similar rate, especially for a simple one-night stop.
Reviewed on Jul 25, 2026

Massanutten Resort
Price was $1,099, price is now $948 per person
$948
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Weyers Cave (SHD)
8/10 Very Good! (1,437 reviews)
I would have scored the stay Higher however there are a few negatives. First the room we stayed in we booked on hotels the condos that are reserved for such guests and not timeshare owners are out of the way up on the mountain and we had no direct access to our unit which meant we had to lug all our luggage down the side of a cliff to our room. The room was ok however the king bed in the room sucked the pull out couches were rock hard and the internet and TV was spotty at best. The other big knock I had was there are only a few things on the property that are free most of the activities cost money and not alittle either. All in all in is a great place to go if you know what you are getting into. Book a timeshare owners suite through apps and bring extra money with you for all the activities. We will come back agian.
Reviewed on Jul 30, 2026


Holiday Inn Express & Suites Waynesboro East by IHG
Price was $612, price is now $559 per person
$559
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Weyers Cave (SHD)
9/10 Wonderful! (607 reviews)
Room was very clean and staff helpful, breakfast had many options.
Reviewed on Jul 30, 2026

Stay near popular Waynesboro attractions
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
$99 nightly
The price is $110 total per night from Aug 30 to Aug 31
$110 total
Aug 30 - Aug 31
Total with taxes and fees
9/10 Wonderful! (614 reviews)
"Room was very clean and staff helpful, breakfast had many options."
Reviewed on Jul 30, 2026

Best Western Plus Waynesboro Inn & Suites Conference Center
109 Apple Tree Ln Waynesboro VA
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $110 total per night from Aug 3 to Aug 4
$110 total
Aug 3 - Aug 4
Total with taxes and fees

Days Inn by Wyndham Waynesboro
2060 Rosser Avenue/I-64 Waynesboro VA
Fully refundableReserve now, pay when you stay
$54 nightly
The price is $60 total per night from Aug 2 to Aug 3
$60 total
Aug 2 - Aug 3
Total with taxes and fees
7.2/10 Good! (1,000 reviews)
"This hotel was decent for the price and worked well for an overnight stay. Check-in was quick, and the staff was friendly. The beds were comfortable, the air conditioning worked well, and we slept great without any noticeable outside noise. The room had been cleaned, but only minimally. There was ..."
Reviewed on Jul 25, 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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- Raven's Roost Overlook
- Factory Antique Mall
- Crozet Vacations
- Wintergreen Resort
- Hermitage Hill Farm & Stables
- Rockfish Gap Entrance Shenandoah
- R.r. Smith Center for History & Art
- Mary Baldwin College
- Afton Mountain Vineyards
- Viette's Gardens
- Flying Fox Vineyard
- War Fields
- The Camera Heritage Museum
- Verona Vacations
- King Family Vineyards
- Veritas Vineyard and Winery
- Visit Afton
- Bold Rock Hard Cider Nellysford Cidery
- Visit Waynesboro
- Swannanoa Palace
- Barren Ridge Vineyards
- Cardinal Point Vineyard and Winery
- Plumb House Museum
- Blue Ridge Parkway North Entrance
- P. Buckley Moss Gallery
- The Woodrow Wilson Presidential Library
- Staunton Vacations
- Zeus Digital Theater
- Ruby Canody Gallery
- Silverback Distillery
- Massanutten Water Park
- Wintergreen Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.


















