
House holiday rentals in Waynesboro
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Top-rated house rentals in Waynesboro
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Popular amenities for house rentals in Waynesboro
House rentals with a pool

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat
We had the absolute best time staying here. We had two families staying together, 10 total. With more than enough space! The location was perfect. The space was clean and cozy. We had the best time and made some amazing memories with our friends. Also we slept at night on the third floor with a window opened and it was so quiet outside! Thank you for opening your home to us!

Farmhouse on Working Vineyard
We stayed here for a bachelorette weekend and had a great time. The house was even bigger and cozier than I anticipated and the views were gorgeous. We loved being on the same property as Cardinal Point Winery and walked down to do a tasting/enjoy some bottles. The kitchen was stocked with all the tools we could have needed and the pool area was great!

Charming Carrie's Cottage at Fairhill Farm
Thank you so much for the great stay! We enjoyed the area and were able to relax at your place.

Peaceful 3-BR Mountain home w/Fireplace + Hot tub
Our family of four needed a quiet get away, and we enjoyed the beautiful days and evenings, inside and on the deck! Hikes nearby, spa nearby, restaurants, grocery, gas also nearby. Great resort year round! Lots of activities if you want them, and lots of peaceful nature if you want. Great!

Bear's Mountain Escape
Great stay! Perfect location and space was great. A tad smaller than what it looked like in the photos, but overall, great! The kitchen did not have any pantry space, but we made do with a shelf above the microwave and bins on top of the fridge. A day prior to check-in, I received an email stating the pool in the complex was closed for repairs. A bit disappointed at first, but it ended up working out really well. We had access to the SPA indoor and outdoor pools and the outdoors ended up being too cold to swim in. The indoor pool was no problem at all and they were very accommodating with lettings us have access throughout our stay. We would stay here again for sure!

Mt. RelaxCATION~on resort~hottub~pool table~arcade
Our stay was everything we could have wanted for a weekend with friends. James was extremely helpful, flexible, and communicative, and the house is clean, well stocked, and packs a lot of space & fun into a small footprint.

Mntn View Hot Tub Pool Table Pool Tennis Golf
A wonderful property nestled in the Wintergreen Resort. While not part of the resort, the amenities and surrounding Breweries offered plenty to do while not relaxing in the hot tub or on the private deck. Beds were comfortable, and there was plenty of space for our family to spread out. Access to WiFi and movie channels were convenient and supplemented the secluded feel for a well balanced vacation. Highly recommend this rental for families and groups looking to get away for a relaxing and enjoyable time in the mountains. Bring your cameras and charge your phones to take pictures of the breathtaking views at and around the house!

Mountain Escape w/ Private Pool & Scenic Trails
Perfectly imperfect! We wanted a getaway from the city and this was just that. Everything that wasn’t “perfect” made our experience more memorable. Sitting out by the fire and waking up to the scenery was amazing. We were also glad to let our dogs run wild.
Weekly house rentals

New Reno! Central to Skyline, Staunton, Cville
Reagan’s an amazing host, from booking to the guide book to check in! The house was beautiful and looked exactly like the pictures. Everything was clean and above our expectations! She was super responsive and gave clear instructions for check in/check out! The guide book was very useful in helping us find things to do in the local area! She went above and beyond for a host!

Unit A-Mountain Retreat- SAUNA-Hiking-Wineries
We had a such a wonderful time! Everything we needed was there and more: plenty of coffee, granola bars for the hikes, coal for the grill. We felt right at home. Thank you for this wonderful place!

Jay Birds Nest - Pet Friendly
This is our favorite place to stop on the half way point of our trips! Our second stay here was just as incredible as the first and the snacks are so appreciated!!

The Nest
Really beautiful place with lots of character! So peaceful and amazing views!! We loved it. :). Thanks Julie!

Living Water Farm, Blue Ridge
This home and hosts are both rare gems, from the ease of checking in to the homes beautiful ambiance, its makes a great place to get away and enjoy nature. We would love to come back and explore more of the trails and wineries.

"The Shire" at Hollow View: Crozet Farmhouse
This property was just perfect for a weekend meeting up with old friends for a local wedding. The area is gorgeous and peaceful, and the porches in the front and back of the house are a lovely sitting area to spend time. The layout of the house is great and feels spacious while also being cozy. The only thing to keep in mind is that there is only one bathroom - certainly not a dealbreaker but it required some juggling with 6 people in the house. Overall 10/10 and we were reluctant to leave!

Shifflett's Ole Homeplace - serene river getaway
Adorable cottage! Great location, very quiet and peaceful with just the sound of the creek. Very comfortable accommodations. Would highly recommend!

The Washhouse
Trisha & Derrick’s farm is located in a valley in the Appalachian mountains, not far from Shenandoah National Park and the WV border. It’s a beautiful and peaceful property inhabited by farm animals, two easy-going and very sweet dogs, and their young family. Trisha, two of her beautiful children and their dogs greeted us when we arrived. We got to learn a little bit about their animals and make friends with their dogs and pigs. The Washhouse is a cozy house on their property. It’s quite spacious on the inside, insanely clean, and decorated with love and care. We felt right at home. We only stayed one night but we’d definitely stay there again.
Private house rentals

Orso Blu one-of-a-kind VIEWS in Crozet
The house is in a beautiful setting surrounded by mountains with peaceful views from the front porch that include a field of lavender and a stream. A forested trail network can be accessed at the far end of the lavender field--so bring your hiking shoes. The house is stunning with clean lines, "european" design and decor that includes high-end appliances and fixtures. Francesca is the ultimate host-very friendly and helpful. She provided all the information and details on the house that you would need for an easy check-in, stay, and check-out. From my initial conversations with her when I booked the house to helpful messages just before and during our stay, I felt like I was staying at the house of an old friend. We look forward to staying at Orso Blu on a future trip!

Cute Place in Waynesboro
We had a great stay here! Everything was super clean and great location. Clarence was very responsive and helpful with local recommendations!

•Staunton | Boho Bungalow•
We we're in town to visit our grandmother so we didn't spend a whole lot of time at the house but it worked perfectly for what we needed it for!

Enchanting, historic home - short walk to downtown
The Sweet Little Darling stay was charming and comfortable. I only wish we could have stayed longer to gain even more of a feel for the place and the area. The home is an effective blend of historic detail and modern convenience. We had a toddler with us, and so understandably, we were especially mindful in using the front and back stairways. The place is one of the cleanest Airbnbs in which I’ve stayed and definitely deserves its “5” rating.

Dayton Guesthouse
Clean and charming place to stay for my parents who were visiting town for the weekend. Love that it was dog friendly, too.

"Glass & Pine" Home close to Bold Rock &Vineyards
Lovely place, very clean, stylishly decorated. It is roomy and has a fantastic view. Nice outdoor sitting areas. It is secluded. The only problem my family and I ran into was knowing what driveway to turn in. We failed to see a sign that displayed a house number at the end of the driveway. Other than that the house and our stay was outstanding.

Mountain Homestead - Hottub, King, Dogs, Gameroom
The photos don’t do it justice - the views were immaculate, the location was excellent, and the home was a piece of serenity in Afton. Wendy was a wonderful host, very responsive, and kind. Would rent this again in a heartbeat.

Blueridge, breweries, hiking within 10 minutes!
Great house with 1920s charm and updated amenities. Quiet and safe neighborhood. The kitchen was fairly well stocked for cooking in. Big, beautiful fenced in yard for kids or dogs. Highly recommend!
Quick stats about house rentals in Waynesboro
Total rentals
30 properties
Nightly prices starting at
₹1,735 before taxes and fees
Total number of reviews
1.5K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Massanutten Resort
- Luray Caverns
- Ash Lawn-Highland
- Early Mountain Winery
- Boonsboro Country Club
- Chisholm Vineyards at Adventure Farm
- Prince Michel Winery
- Spring Creek Golf Club
- Amazement Square
- Massanutten Ski Resort
- Wintergreen Resort
- The Plunge Snow Tubing Park
- Frontier Culture Museum
- Car and Carriage Caravan Museum