A wooden mill with a water wheel, surrounded by autumn foliage and a calm river.

Waynesboro Holiday Rentals

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Our top choices for Waynesboro holiday rentals

1. The Guest Wing at Kateri

The Guest Wing at Kateri
2.0 star property
Waynesboro
10.0 out of 10, Exceptional, (1 review)
"The property was amazing, beyond wonderful. Gracious host. High end furniture and bedding. The backyard and pool area were just beautiful !!! I wish I stayed earlier in the year so i could enjoy the pool. The property is surrounded by wide open farm lands, Starry skies, birds and crickets. It was a very relaxing stay. I wish I could stay longer !!!"
United States
Barbara
The price is NZ$623
includes taxes & fees
16 Nov - 17 Nov
The Guest Wing at Kateri

2. Blue Ridge Hideaway

Blue Ridge Hideaway
2.0 star property
Waynesboro
The price is NZ$436
includes taxes & fees
10 Nov - 11 Nov
Blue Ridge Hideaway

3. The Wayne Shire

The Wayne Shire
2.0 star property
Waynesboro
The price is NZ$903
includes taxes & fees
10 Nov - 11 Nov
The Wayne Shire

4. The Farmhouse at Wellington

The Farmhouse at Wellington
2.0 star property
Waynesboro
The price is NZ$1,025
includes taxes & fees
15 Nov - 16 Nov
The Farmhouse at Wellington

5. Kateri

Kateri
2.0 star property
Waynesboro
Kateri

6. Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (282 reviews)
"Clean room convenient parking, good kitchen, friendly staff."
United States
Jamie
The price is NZ$229
includes taxes & fees
10 Nov - 11 Nov
Valley Extended Suites

7. Afton View Lodge

Afton View Lodge
3.0 star property
Afton
The price is NZ$1,079
includes taxes & fees
30 Nov - 1 Dec
Afton View Lodge

8. Afton Mountain Vineyards

Afton Mountain Vineyards
3.5 star property
Afton
7.4 out of 10, Good, (3 reviews)
"Cozy and comfortable with pond and mountain views. Wine tasting on site and easy access to Wintergreen. We loved our stay and will be back again!"
United States
Jennifer
The price is NZ$738
includes taxes & fees
15 Nov - 16 Nov
Afton Mountain Vineyards

9. Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
9.6 out of 10, Exceptional, (30 reviews)
"This place was excellent. Very clean and quiet. Sherando lake was only 4 miles away with great hiking trails. The beds were very comfortable. Would definitely stay at this place again."
United States
Josh
The price is NZ$329
includes taxes & fees
10 Dec - 11 Dec
Love Ridge Mountain Lodging

10. Enjoy Staunton in the Heart of Shenandoah Valley

Enjoy Staunton in the Heart of Shenandoah Valley
3.0 star property
Staunton
The price is NZ$861
includes taxes & fees
9 Dec - 10 Dec
Enjoy Staunton in the Heart of Shenandoah Valley

11. SONSAK - MONTICELLO

SONSAK - MONTICELLO
3.5 star property
Charlottesville
10.0 out of 10, Exceptional, (12 reviews)
"Excellent For Couples Getaways!!!"
United States
Jonathan
The price is NZ$225
includes taxes & fees
10 Nov - 11 Nov
SONSAK - MONTICELLO

12. Swannanoa Guest House

Swannanoa Guest House
2.0 star property
Afton
The price is NZ$1,274
includes taxes & fees
10 Nov - 11 Nov
Swannanoa Guest House

13. Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is NZ$1,173
includes taxes & fees
10 Nov - 11 Nov
Modern Nellysford Getaway on 40 Private Acres!

14. Fox Hill

Fox Hill
2.0 star property
Afton
The price is NZ$904
includes taxes & fees
10 Nov - 11 Nov
Fox Hill

15. Mountaintop Wintergreen Resort Home w/ Deck, Views

Mountaintop Wintergreen Resort Home w/ Deck, Views
3.0 star property
Nellysford
10.0 out of 10, Exceptional, (1 review)
The price is NZ$913
includes taxes & fees
10 Nov - 11 Nov
Mountaintop Wintergreen Resort Home w/ Deck, Views

16. Magnolia Suite

Magnolia Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (1 review)
"Great location in small town with some restaurants and shops. The room was spacious and light with high quality interior and design - very nice!!"
Norway
Christian
The price is NZ$398
includes taxes & fees
10 Nov - 11 Nov
Magnolia Suite

17. Fishersville Oasis

Fishersville Oasis
2.0 star property
Fishersville
2.0 out of 10, (1 review)
The price is NZ$522
includes taxes & fees
11 Nov - 12 Nov
Fishersville Oasis

18. The Reserve at 151

The Reserve at 151
2.0 star property
Afton
10.0 out of 10, Exceptional, (1 review)
The price is NZ$1,157
includes taxes & fees
10 Nov - 11 Nov
The Reserve at 151

19. Staunton Underground

Staunton Underground
2.0 star property
Staunton
10.0 out of 10, Exceptional, (2 reviews)
"Enjoyed the apartment (felt at home) and enjoyed our first visit to Stauton Virginia. Passing through with our two dogs and needed a place to stay that we felt comfortable. Apartment was perfect location to walk around and look at all of the history this city has. Already planning on coming back!"
United States
Heather
Staunton Underground

20. The Serendipity Suite

The Serendipity Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (9 reviews)
"Electric charger and air-conditioning were key this weekend. Great location with easy walk to restaurants, entertainment and shops."
United States
Jennifer
The price is NZ$354
includes taxes & fees
16 Nov - 17 Nov
The Serendipity Suite
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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Top Waynesboro Hotel Reviews

Find out more about Waynesboro

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Waynesboro holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Waynesboro. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Waynesboro. Seeing all the best attractions is bound to make you fall in love with Waynesboro. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Waynesboro short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Waynesboro?

Yes, there are holiday rentals in Waynesboro close to Shenandoah Valley Art Center, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Waynesboro. While you're here, grab a bite or have a drink at the wineries.

What are some of the best holiday rentals that Waynesboro has to offer?

Mountainside Villas at Massanutten by Tripforth: This holiday home rental outside of Waynesboro is located near skiing, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Amenities such as kitchenware and free parking are also available for your convenience. You and your friends and family can relax into your holiday with amenities such as an outdoor tennis court.

How many holiday rentals are there in Waynesboro?

With 30 Expedia holiday rentals, you're guaranteed to find just the right place for your Waynesboro stay.

What can I see and do in Waynesboro?

Cultural attractions include Wayne Theatre and Waynesboro Heritage Museum, whereas Shenandoah National Park and Rockfish Gap Entrance Shenandoah are a couple of picturesque spots to enjoy the outdoors. While here, George Washington National Forest and Shenandoah Valley Art Center are other places worth a visit.

What are holiday rentals like in Waynesboro?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Waynesboro. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.