House vacation rentals in Waynesboro

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Popular amenities for Waynesboro house rentals

House rentals with a pool

Top guest favorite
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 favorite
A charming farmhouse with a white exterior and green shutters is surrounded by lush gardens. A small round table with white chairs sits among blooming azaleas. Two large trees provide shade in the front yard, complementing the inviting porch.
Home in Afton
4.94 out of 5 average rating, 144 reviews

Farmhouse on Working Vineyard

SarahRating, 5 stars1 week 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 favorite
A serene outdoor space is captured, featuring a sparkling pool surrounded by lounge chairs and a dining table. Lush greenery and blooming flowers frame the scene, creating a tranquil atmosphere with expansive mountain views in the background under a clear blue sky.
Home in Stanardsville
4.98 out of 5 average rating, 147 reviews

Charming Carrie's Cottage at Fairhill Farm

YuRating, 5 stars2 weeks ago
Thank you so much for the great stay! We enjoyed the area and were able to relax at your place.
Guest favorite
A modern living area features a sleek leather sectional sofa adorned with patterned cushions, accompanied by a wooden coffee table. Large windows offer views of the surrounding trees, while natural light enhances the inviting space. A floor lamp adds illumination next to the sofa.
Home in Wintergreen Resort
4.96 out of 5 average rating, 106 reviews

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

NikiRating, 5 stars1 month 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!
Top guest favorite
A wooden walkway leads to the entrance of the house, framed by vibrant pink rhododendron flowers. Tall trees provide a natural backdrop, with dappled sunlight filtering through the leaves, creating a serene outdoor setting.
Home in Wintergreen Resort
4.96 out of 5 average rating, 113 reviews

Bear's Mountain Escape

BrianneRating, 5 stars2 weeks ago
This is a very cute, clean condo with everything you need to feel comfortable. The master bed is very comfortable, which is always a huge plus for AirBnBs! Having the Wintergreen market and a couple restaurants within walking distance was great, and this is a great "base camp" for plenty of beautiful hiking, wineries, and scenery in the area.
Guest favorite
A spacious bedroom features a high, wood-beamed ceiling and a large window providing natural light. The bed is dressed in navy bedding with a plaid blanket draped across it. A wooden dresser and lamp complement the rustic decor, and a mounted TV is positioned above.
Home in Wintergreen Resort
4.97 out of 5 average rating, 197 reviews

Hottub Ski In/Ski Out Renovated Chalet Lower Tyro

AshleighRating, 5 stars2 weeks ago
Joes property was absolutely beautiful! The views are amazing from the cozy hot tub on the back porch. Everything was super clean and the beds were super comfortable! This airbnb would be great for a family stay or a friends getaway. It was everything we needed and more! Joe was quickly responsive when i had questions. This air bnb is stocked with EVERYTHING you may need. Beautiful spot, 10/10!
Superhost
A spacious open living area features large windows offering natural light and views of the outdoors. The area includes a comfortable sofa, dining space with chairs, and a modern kitchen equipped with a stylish island and fixtures, enhancing the room's contemporary rustic feel.
Home in Wintergreen Resort
4.79 out of 5 average rating, 104 reviews

Mntn View Hot Tub Pool Table Pool Tennis Golf

JeremyRating, 5 stars2 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
An outdoor pool is set in a tranquil area, surrounded by lush greenery and colorful flowers. Poolside loungers and umbrellas are positioned along the edge, providing shaded seating. The clear blue water invites relaxation under the sun, while a gentle slope leads to the pool entrance.
Home in Schuyler
4.79 out of 5 average rating, 111 reviews

Peaceful Cottage

EvelynRating, 5 stars8 months ago
We stayed at Diana’s place while visiting with our daughter for our annual apple picking trip. Her place was a bit far out away from things, which we expected. It was cozy and had everything we needed for the weekend. I would highly recommend this cozy cottage when you want to get away!

Weekly house rentals

Top guest favorite
An open living area showcases a spacious sectional sofa facing a round coffee table. Wooden beams are visible on the ceiling, while large sliding glass doors lead to the backyard. A dining table for several is positioned nearby, creating a seamless flow between spaces.
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!
Top guest favorite
A panoramic view of rolling mountains is framed by lush green treetops. Soft mist blankets the valleys below, gently illuminated by the sunlight above. The vibrant sky showcases clear blue hues with wisps of clouds, creating a serene and peaceful atmosphere.
Home in Wintergreen Resort
4.96 out of 5 average rating, 105 reviews

Cliffs Edge- Hike, Play & Splash into Summer!

OmarRating, 5 stars1 month ago
Amazing place! My family and I thoroughly enjoyed our stay. Great home with breathtaking views of the Blue Ridge Mtns and tranquility for days! Julie was a superb host. Her hospitality, directions and communication were second to none. Thank you and we look forward to visiting again.
Guest favorite
Home in Crozet
5 out of 5 average rating, 15 reviews

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

JamesRating, 5 stars1 week 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!
Top guest favorite
The exterior view showcases a modern blue house set against a backdrop of lush green hills. A wooden deck extends from the home, providing access to outdoor space. The gravel driveway is lined with a rustic split-rail fence, enhancing the natural feel of the surroundings.
Home in Nellysford
4.97 out of 5 average rating, 117 reviews

Llama Loft | No Service Fee | Fire Pit

MelissaRating, 5 stars3 weeks ago
Great house layout with a beautiful porch and lots of parking. The host is very responsive and helpful. It’s a little off the beaten path but close to lots of breweries and wineries. Would absolutely stay here again.
Guest favorite
A charming cabin is positioned on a stone patio, framed by trees. The early morning sun casts warm light over the scene, enhancing the natural landscape. A fire pit is visible in the foreground, surrounded by a low stone wall, creating an inviting outdoor gathering space.
Home in Chester Gap
4.95 out of 5 average rating, 227 reviews

The Nest

ChristopherRating, 5 stars2 weeks ago
Really beautiful place with lots of character! So peaceful and amazing views!! We loved it. :). Thanks Julie!
Top guest favorite
A charming cottage with a peaked roof features a welcoming red door. Surrounding gardens with colorful flowers and lush greenery enhance the entryway, while a gravel path leads to the entrance. Trees provide a natural backdrop, contributing to the serene setting.
Home in Keswick
4.99 out of 5 average rating, 841 reviews

Charming Cottage at Golden Hill

JeremyRating, 5 stars6 days ago
Patricia was an amazing hostess. Very gracious made it a home away from home. It was hard to leave for our concert nearby. Very relaxing cabin,we even slept very well there. Normally we don’t sleep well when we are away from home.
Top guest favorite
An aerial view of a downtown neighborhood is displayed, showcasing a mix of historic homes and trees. The landscape features rolling hills in the distance, with a blend of residential streets and parked vehicles visible.
Home in Staunton
5 out of 5 average rating, 209 reviews

* Award-Winning Renovation * Ideal Location *

TerryRating, 5 stars1 week ago
The house was spacious, comfortable, and felt like home. Chris was so helpful with all the details he provided to make it a fun and relaxing visit. Hope to visit again sometime.
Top guest favorite
Home in Waynesboro
5 out of 5 average rating, 32 reviews

"Virginia Beauty" in Historic Tree Streets

HunterRating, 5 stars1 week ago
Virginia Beauty was indeed a beauty! We traveled back east for a long overdue family gathering and loved this little corner on the historic Tree Streets. The house was full of character and history, and my family and I enjoyed each space, whether lounging or reading or enjoying coffee among a chorus of birdsong. Would love to book again when in town!

Private house rentals

Top guest favorite
The exterior of a single-story home is shown, featuring a welcoming porch with a wooden front door and two chairs. Lush greenery and blooming hydrangeas surround the entrance, with expansive lawn space and a cloudy blue sky above, creating a serene outdoor atmosphere.
Home in Waynesboro
4.98 out of 5 average rating, 57 reviews

Willow Grove Wineries, Breweries, Hiking,Hot Tub

JamesRating, 5 stars2 weeks ago
Loved this beautiful home and property in Waynesboro!! This was our second time here. Love the privacy, our dogs love the large yard for playing, and the close proximity to Shenandoah National Park. This home is very clean, well stocked, and has all the comforts of home. We loved the patio to eat dinner, hung out at the firepit at night and used the hot tub after a long hike. We will hopefully be back next year.
Top guest favorite
A spacious home is positioned atop a gently sloping, lush green knoll. Its architecture combines modern design with natural surroundings. The expansive front porch offers a welcoming entry, while the backdrop features a clear sky transitioning from daylight to dusk.
Home in Afton
5 out of 5 average rating, 33 reviews

The Vū, Afton w/ 360º Mountain Views

KristaRating, 5 stars3 weeks ago
We could not have asked for a better stay at the Vū. The home was as beautiful as the photos and the scenic background made it hard to leave. The house is near several vineyards and popular local spots but is set back from the road and neighbors, so felt very private. It’s clear that Emily put careful thought into every detail of the space, from the furniture to the amenities and fully-stocked kitchen. The screened porch was an exceptional feature. I stayed with my family and the space was more than enough to accommodate all of us. I absolutely recommend the Vū for your next mountain getaway!
Guest favorite
A dining area is showcased with a stylish table set for six. Dark blue cabinets contrast with a floral wallpaper design. A circular mirror hangs on the wall, reflecting natural light. A colorful area rug adds warmth to the wooden floor beneath.
Home in Staunton
4.96 out of 5 average rating, 26 reviews

•Staunton | Boho Bungalow•

MargaretRating, 5 stars6 days ago
Devan's place is spacious, comfortable and nicely decorated. You can see the care that went into the furniture and decor choices. Easy parking and nice bathroom products.
Top guest favorite
A cozy bedroom features a spacious white bed adorned with a textured quilt and decorative pillows in soothing green and blue hues. Two bedside tables with lamps flank the bed, providing soft lighting, while elegant vases add a touch of style to the space.
Home in Staunton
5 out of 5 average rating, 68 reviews

Enchanting, historic home - short walk to downtown

Rita McGillRating, 5 stars1 week 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.
Top guest favorite
Home in Nellysford
5 out of 5 average rating, 17 reviews

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

ChastityRating, 5 stars2 weeks ago
We enjoyed a Grirl's Trip! The place was beautiful and so tastefully decorated! Wish we could have stayed more than one night! Would definitely book again!
Top guest favorite
A spacious deck features two lounge chairs and two wooden rocking chairs, offering a setting for relaxation. The surrounding area showcases lush green mountains under a clear blue sky, with expansive views of the valley below.
Home in Afton
4.97 out of 5 average rating, 36 reviews

Mountain Homestead - Hottub, King, Dogs, Gameroom

AlexRating, 5 stars1 week 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.
Superhost
An A-frame cabin with a modern exterior features a sloped roof and large glass windows. A spacious deck extends from the upper level, adorned with outdoor seating. Surrounding greenery and a gravel area provide a serene backdrop, showcasing the home's integration with nature.
Home in Lyndhurst
5 out of 5 average rating, 4 reviews

Luxury A-Frame w/ Views, Hot Tub & Media Room

JoshuaRating, 5 stars1 week ago
This was a one of a kind house that was on the side of the mountain. The views were great and the peacefulness was perfect. Definitely worth a visit and I hope to come again!!
Guest favorite
A charming brick home is presented with a gabled roof and a welcoming front porch. Lush green lawns and white hydrangeas surround the entrance. The pathway leads to a central door, framed by two large windows, creating a warm and inviting exterior.
Home in Waynesboro
4.86 out of 5 average rating, 51 reviews

Blueridge, breweries, hiking within 10 minutes!

ErinRating, 5 stars5 days 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

    ﺩ.ﺇ73 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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