House holiday rentals in Waynesboro

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Popular amenities for house rentals in Waynesboro

House rentals with a pool

Top guest favourite
Home in Wintergreen Resort
4.88 out of 5 average rating, 136 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

KatieRating, 5 stars3 months ago
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!
Guest favourite
Home in Afton
4.94 out of 5 average rating, 144 reviews

Farmhouse on Working Vineyard

SarahRating, 5 stars2 weeks ago
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!
Top guest favourite
Home in Stanardsville
4.98 out of 5 average rating, 147 reviews

Charming Carrie's Cottage at Fairhill Farm

YuRating, 5 stars3 weeks ago
Thank you so much for the great stay! We enjoyed the area and were able to relax at your place.
Guest favourite
Home in Wintergreen Resort
4.96 out of 5 average rating, 106 reviews

Peaceful 3-BR Mountain home w/Fireplace + Hot tub

NikiRating, 5 stars2 months ago
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!
Guest favourite
Home in Wintergreen Resort
4.97 out of 5 average rating, 115 reviews

Bear's Mountain Escape

LauraRating, 5 stars1 week ago
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!
Top guest favourite
Home in McGaheysville
4.97 out of 5 average rating, 134 reviews

Mt. RelaxCATION~on resort~hottub~pool table~arcade

AbbeyRating, 5 stars3 weeks ago
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.
Superhost
Home in Wintergreen Resort
4.79 out of 5 average rating, 104 reviews

Mntn View Hot Tub Pool Table Pool Tennis Golf

JeremyRating, 5 stars3 weeks ago
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!
Superhost
Home in Lovingston
4.85 out of 5 average rating, 298 reviews

Mountain Escape w/ Private Pool & Scenic Trails

JunRating, 5 stars8 months ago
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

Top guest favourite
Home in Waynesboro
5 out of 5 average rating, 14 reviews

New Reno! Central to Skyline, Staunton, Cville

KaitlynRating, 5 stars1 month ago
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!
Guest favourite
Home in Madison
4.96 out of 5 average rating, 418 reviews

Unit A-Mountain Retreat- SAUNA-Hiking-Wineries

GudrunRating, 5 stars1 week ago
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!
Top guest favourite
Home in Edinburg
4.97 out of 5 average rating, 514 reviews

Jay Birds Nest - Pet Friendly

AlyssaRating, 5 stars1 week ago
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!!
Guest favourite
Home in Chester Gap
4.95 out of 5 average rating, 227 reviews

The Nest

ChristopherRating, 5 stars3 weeks ago
Really beautiful place with lots of character! So peaceful and amazing views!! We loved it. :). Thanks Julie!
Top guest favourite
Home in Dyke
4.96 out of 5 average rating, 307 reviews

Living Water Farm, Blue Ridge

BonnieRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Crozet
4.97 out of 5 average rating, 109 reviews

"The Shire" at Hollow View: Crozet Farmhouse

MerielleRating, 5 stars3 weeks ago
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!
Guest favourite
Home in Stanardsville
4.91 out of 5 average rating, 117 reviews

Shifflett's Ole Homeplace - serene river getaway

ColleenRating, 5 stars4 days ago
Adorable cottage! Great location, very quiet and peaceful with just the sound of the creek. Very comfortable accommodations. Would highly recommend!
Top guest favourite
Home in Harrisonburg
4.96 out of 5 average rating, 251 reviews

The Washhouse

AnnaRating, 5 stars4 days ago
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

Guest favourite
Home in Crozet
5 out of 5 average rating, 15 reviews

Orso Blu one-of-a-kind VIEWS in Crozet

JamesRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Waynesboro
4.97 out of 5 average rating, 38 reviews

Cute Place in Waynesboro

AmyRating, 5 stars1 week ago
We had a great stay here! Everything was super clean and great location. Clarence was very responsive and helpful with local recommendations!
Guest favourite
Home in Staunton
4.96 out of 5 average rating, 27 reviews

•Staunton | Boho Bungalow•

ChelseaRating, 5 stars1 day ago
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!
Top guest favourite
Home in Staunton
5 out of 5 average rating, 68 reviews

Enchanting, historic home - short walk to downtown

Rita McGillRating, 5 stars2 weeks ago
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.
Superhost
Home in Dayton
5 out of 5 average rating, 3 reviews

Dayton Guesthouse

ChloeRating, 5 stars2 weeks ago
Clean and charming place to stay for my parents who were visiting town for the weekend. Love that it was dog friendly, too.
Top guest favourite
Home in Nellysford
5 out of 5 average rating, 19 reviews

"Glass & Pine" Home close to Bold Rock &Vineyards

SaraRating, 5 stars1 week ago
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.
Top guest favourite
Home in Afton
4.97 out of 5 average rating, 36 reviews

Mountain Homestead - Hottub, King, Dogs, Gameroom

AlexRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Waynesboro
4.86 out of 5 average rating, 51 reviews

Blueridge, breweries, hiking within 10 minutes!

ErinRating, 5 stars1 week ago
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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