Pet-friendly holiday rentals in Waynesboro

Home in Wintergreen Resort

A welcoming living area features two leather couches arranged around a wooden coffee table, which is complemented by a patterned rug. Large windows allow natural light to illuminate the space, offering views of the surrounding trees. Sliding glass doors provide access to an outdoor deck.

4.99 out of 5 average rating, 150 reviews

Close to skiing! | King Beds | Fireplace | Hot Tub

Welcome to Blackrock Escape! Dog friendly, 2BR/2.5BA mountain home in prime location at Wintergreen Resort. 3-min drive to the Mountain Inn. Walk to hiking trails–the Plunge Trail/Blackrock Park is only a 2-min walk. Two BRs on first floor - both with King-size Helix mattresses, smart TVs, and en suite bathrooms. Wood burning fireplace, games, puzzles, 65” smart TV in living room. Two decks w/gas grill and hot tub. Keurig K-Duo coffee maker and dishwasher in kitchen. Full-sized washer and dryer.

4.89 out of 5 average rating, 101 reviews

A cozy living room features a classic brick fireplace surrounded by comfortable seating. A colorful area rug adds warmth, while large windows offer views of the greenery outside. Adjacent, a vibrant game room contains a foosball table and warm lighting, ideal for entertainment.

Home in Waynesboro

Gameroom~Gym~Firepit~Main Level BR~Pet OK~Downtown

Centrally located historic home walkable to river, downtown shops & restaurants. Less than 15 mins to Shenandoah Natl Park, Blue Ridge Pkwy, Skyline Drive, Blue Ridge Tunnel Hike, Basic City Brewery, The Foundry, Wineries, Antique shops & Augusta Expo. Charlottesville, Staunton, Harrisonburg & Nelson Ski/Wineries 30mi The rec center across the street has playground & basketball court. Home has a main level bed & bath, game room, gym, 2 living rooms, firepit, fireplace, king bed & lots of charm!

4.91 out of 5 average rating, 221 reviews

A charming cottage exterior showcases a green facade with textured wood siding, complemented by a welcoming porch. Outdoor seating is provided by rustic chairs around a fire pit on the lawn. A table nearby offers an inviting spot for dining, set against a backdrop of distant mountains.

Cottage in Crozet

Idyllic Cottage Retreat

⭐️ Condé Nast Traveler Approved ⭐️ Cozy cottage nestled on a historic 400-acre Blue Ridge Mountain farm abutting Shenandoah National Park. Every space inside this cozy cottage is creatively styled, with tons of perfectly imperfect charm. Outside, a hammock beneath the elm trees, fire pit and grill, all allow for enjoying the splendor of this peaceful enclave. Excellent day-tripping to many of central Virginia's celebrated wineries and breweries, as well as scenic drives and hiking trails.

4.75 out of 5 average rating, 512 reviews

The exterior features a two-story home with a welcoming red front door. The entrance is accessible by a wooden staircase, surrounded by a deck and landscaped with trees and fallen leaves. A paved driveway accommodates parking for multiple vehicles.

Flat in Waynesboro

Spacious lower level Airbnb! READ SUMMARY!

Hello everyone! I’m not going to try to convince you to stay at this Airbnb but instead address the issues that guests have complained about in reviews. This listing is priced accurately and cheap because there isn’t much besides 2 king beds, bathroom, washer/dryer. There is a bit of noise from upstairs when people walk around but usually no later than 11 PM. Please keep in mind when reviewing that you’re not paying very much to stay here. If you’re going to complain, please stay elsewhere.

4.94 out of 5 average rating, 171 reviews

A modern tiny house is nestled among trees, showcasing a wooden exterior with deep red accents. Large windows provide natural light, while a well-maintained set of steps leads up to the entrance, inviting guests to enjoy the surrounding forest.

Tiny home in Staunton

Sunrise Casita: a tiny house at Cana Barn

Our 250 sq ft tiny house was built by our talented craftswoman Kara. We used wood from our property and reclaimed materials to create a cozy and unique getaway. The front porch looks out to a beautiful view of the Blue Ridge Mountains and looks up to a local vintage sign. We are LGBTQ+ welcoming. Sunrise to us is the embodiment of a fresh start and a new opportunity. It is hope and possibility, adventure and inspiration, beauty and wonder. We hope all of this for your stay in our tiny house!

4.9 out of 5 average rating, 314 reviews

The exterior of the cottage features a welcoming porch with two seated chairs and a wooden railing. Lush greenery and trees surround the cottage, complemented by a beige wooden fence that offers privacy. A clear blue sky brightens the scene, enhancing the inviting atmosphere.

Bungalow in Waynesboro

The Copper Cottage - near the Appalachian Trail

An antique fully renovated, cozy cottage that blends the character of saw milled wood beams, hand-crafted finishes, & local art with the modern comforts of Wi-Fi, Streaming TV, A/C, and a Jetted shower that might raise your attitude with the altitude! At the entrance to downtown Historic Waynesboro and the riverside park, its restaurants and stores can entertain even the peculiar palate or collector, some are right across the street! Fully fenced in back yard, so bring the pups to play!

4.83 out of 5 average rating, 510 reviews

The open living area features a dining table with wooden finish surrounded by blue chairs. A comfortable couch is positioned nearby, and a TV sits atop a low table. Natural light floods in through multiple windows, illuminating light-colored walls and a patterned rug.

Chalet in Afton

Chalet house next to wineries/breweries!

Barn style chalet in the center of all the wineries, breweries, distilleries, cideries, Shen. National Park, hiking, App.Trail, Blue Ridge Pkwy, Wintergreen Resort. Pets welcome for an added fee ($40) per pet. Located on 151 -"alcohol alley". Literally seconds to Blue Mountain Brewery or Flying Fox Vineyard & a minute or two drive to Veritas, Cardinal Point, Afton Mt, Silverback, Valley Rd & so many more! Fiber internet, disinfected, whole foods delivers groceries here. Great spot!

4.99 out of 5 average rating, 418 reviews

The cottage is framed by tall trees and lush greenery. It features a welcoming front porch with wooden posts, surrounded by well-maintained grass. A glimpse of a rustic barn is visible in the background, adding to the serene farm setting.

Farm stay in Weyers Cave

LuxuryFarmCottage: Hot Tub, Sauna, ShenandoahViews

Welcome to the Cottage at Dices Spring Farm. This gem is nestled in the beautiful Shenandoah Valley. You will love the weather-sheltered hot tub building, relaxing greenhouse garden massage space and personal finely crafted sauna with a Sweden built cold shower dump bucket A custom bathroom double-headed shower, and reading nook in the loft are favorites to unwind and disconnect. Minutes away from JMU, Buc-ee's, Valley Pike Market & Vineyards.

4.96 out of 5 average rating, 408 reviews

A charming outdoor space features a small round blue table and two matching folding chairs. A green potted plant sits at the center of the table. Light filters through the large windows, which are framed by red brick walls.

Flat in Staunton

Travelers Nook - close to downtown

The TRAVELERS NOOK is a cute, cozy, one bedroom apartment close to downtown Staunton! It’s located on the second floor, with a private entrance. It has all the charm that you would expect to find in a cute studio apartment! Built by a local architect Tj Collins in the 1920’s. This quaint space has everything you need to enjoy your stay here in Staunton! We do accept small pets on approval with a pet cleaning charge.

4.92 out of 5 average rating, 347 reviews

A charming white bungalow is shown, featuring a welcoming yellow front door and dark shutters. Sunlight filters through the trees, highlighting the neatly landscaped front yard and walkway leading to the entrance.

Bungalow in Waynesboro

Cheerful 2 bd bungalow with HOT TUB! Pet friendly!

Enjoy the entire home to yourself, including a relaxing backyard retreat with hot tub. Perfect for singles or couples who want to stay home and relax or visit the sites then come home to enjoy the hot tub under the stars. 10 min drive to shopping; 10 min to Blue Ridge Parkway & Skyline Drive; 15 min to 151 Breweries. kayaking/canoeing/hiking/fishing on the beautiful South River.

A spacious living area is furnished with a comfortable couch adorned with multiple pillows. A wooden coffee table sits on a textured rug, complemented by a small side table with a plant. Bright light emanates from a floor lamp, while a ceiling fan provides air circulation.

4.89 out of 5 average rating, 130 reviews

Blue Ridge Retreat: Your Cozy Mountain Getaway

Luxury condo furnished with all you need for an exceptional stay. Whether you enjoy the wineries and breweries, hiking the mountain trails, kayaking or paddleboarding, or ski/snowboard, this is the perfect home base for everything Wintergreen has to offer! Just 3/4 of a mile to the resort & slopes and a 50 foot walk from your back door to the shuttle pickup.

4.95 out of 5 average rating, 260 reviews

The farmhouse features a welcoming exterior with a red front door and a broad porch. A concrete pathway leads to the entrance, flanked by well-maintained green grass and several small trees. The surrounding landscape includes open fields visible in the background.

Farm stay in Waynesboro

Farmhouse at the foot of the Blue Ridge Mountains

Updated, pet-friendly farmhouse with extra-large fenced in yard, located in Waynesboro. Located on a 60 acre farm surrounded by nearly a mile of river - 10 minutes from Skyline Drive & Blue Ridge Parkway - 15 minutes to Rt. 151, with unlimited wineries and breweries - 30 minutes to Charlottesville, UVa -30 minutes from Wintergreen

Popular amenities for Waynesboro pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.92 out of 5 average rating, 283 reviews

The exterior of a single-story ranch house is presented, featuring light siding and a sloped roof. A well-maintained front yard includes manicured shrubs and flowering plants. Steps lead to the front door, framed by two windows on either side, with a clear walkway visible in the foreground.

Home in Locust Grove

Locust Grove Retreat- 3 Bed, 1 Bath, Full Kitchen

4.91 out of 5 average rating, 106 reviews

A two-story house is set amidst vibrant autumn foliage, showcasing a covered porch that invites relaxation. A garage is visible on the left, with a gravel driveway leading to the entrance. Sunlight filters through trees, illuminating the exterior of the home.

Home in Crozet

Beauchamp House 2 BD Fishing Hiking Lake

4.99 out of 5 average rating, 886 reviews

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

Charming Cottage at Golden Hill

Home in Wintergreen Resort

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.

4.94 out of 5 average rating, 141 reviews

Bear's Mountain Escape

4.99 out of 5 average rating, 148 reviews

A three-story wooden house is nestled among lush greenery in a forested setting. The deck and patio area are accessible, surrounded by trees and natural landscaping, creating a serene environment for relaxation.

Home in Nellysford

Cabin Retreat | Family & Dog Friendly | Fire Pit

4.97 out of 5 average rating, 108 reviews

A vast expanse of green grass stretches across the foreground, framed by lush orchard trees. Rolling hills covered with foliage rise in the background, under a clear blue sky dotted with soft white clouds, creating a serene rural atmosphere.

Home in Afton

Perfect getaway among the orchards of Batesville

4.94 out of 5 average rating, 440 reviews

A country bungalow is presented in a fenced yard, surrounded by grassy fields. The exterior features a simple design with a front porch, two accessible entrances, and robust landscaping. Nearby trees provide shade, while a clear sky enhances the peaceful rural setting.

Home in Harrisonburg

The Homeplace - Private House with Backyard

4.99 out of 5 average rating, 284 reviews

A charming cottage is positioned alongside a gently flowing trout stream, with a backdrop of lush greenery. Rocks line the water's edge, and a large, fenced yard surrounds the home, providing a peaceful setting. A red roof contrasts beautifully with the natural surroundings.

Home in Tyro

Bear Creek Inn 3 BR House Creekside

Pet-friendly home rentals with a pool

4.96 out of 5 average rating, 160 reviews

Ski-In Ski-Out ~ Mtn Views ~ King Suite

The exterior of a two-story cabin houses warm wooden accents and large windows. The entrance features a welcoming set of wooden steps leading up to a balcony, surrounded by tall trees, with a concrete pathway leading toward it.

4.94 out of 5 average rating, 242 reviews

Eight Minute Walk to Everything

Farm stay in Stanardsville

A serene night scene features a softly lit Airstream under a trellis, surrounded by greenery. The glow from string lights creates a cozy atmosphere, while the tree canopy enhances the sense of seclusion. A path leads towards the well-lit deck area, inviting evening relaxation.

4.92 out of 5 average rating, 787 reviews

Airstream*dog*POOL*HotTub*MTN*relax*GOATS*horses!

A comfortable living area features a spacious gray sofa and a wooden coffee table, positioned on a patterned rug. Light from a nearby lamp and large sliding doors illuminates the space, which offers views of the outdoors. A cozy accent chair completes the inviting setup.

4.96 out of 5 average rating, 223 reviews

New Construction! 1 Bed/2 Bath, pet friendly

Superhost

A cozy living area features natural stone accents around a wood-burning fireplace. A small dining table with two chairs is positioned near large windows, allowing ample natural light. Green accent walls enhance the inviting atmosphere, while a comfortable seating area is visible nearby.

4.9 out of 5 average rating, 205 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

4.95 out of 5 average rating, 473 reviews

An aerial view captures the guest house and the surrounding property, showcasing a spacious grass area and a 30,000-gallon in-ground pool. The pool area features several blue lounge chairs and is framed by mature trees and landscaped pathways.

Cottage in Madison

THE PERFECT HIKING & WINERY COUNTRY RETREAT

4.95 out of 5 average rating, 195 reviews

Ski-in/Ski-out Wintergreen Highlands Condo -Views!

Villa in Wintergreen Resort

A spacious living area is highlighted by large floor-to-ceiling windows, offering views of the surrounding trees. A comfortable gray sofa and a round glass coffee table are present, along with a wooden dining table that seats six. An electric fireplace adds warmth to the space.

4.96 out of 5 average rating, 125 reviews

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10

Private, pet-friendly home rentals

4.86 out of 5 average rating, 331 reviews

A well-lit kitchen area features a blend of modern and rustic elements, including a farmhouse-style island with seating. Light streams through the double French doors, leading to a small dining space with two chairs and a circular rug on the floor.

Guest house in Crozet

Stylish Carriage House Suite near Crozet center

Holiday home in Lovingston

The cabin's exterior is surrounded by lush greenery, featuring a spacious porch with seating and a hot tub nearby. The two-story structure is constructed of wood, with large windows allowing natural light to fill the interior. A picnic table is located in the yard.

4.96 out of 5 average rating, 242 reviews

Ultimate cabin in the mountains

4.92 out of 5 average rating, 634 reviews

An interior view showcases a cozy living space with wooden walls and ceiling, abundant natural light from large windows, and a ceiling fan. A gray sofa is complemented by a colorful throw blanket, while a small dining area with bright chairs is positioned nearby.

Guest house in Afton

Your Perfect Blue Ridge Mountain Hideaway near 151

Guest house in New Market

The exterior view of the cottage features a walkway leading to a white door, flanked by climbing roses and hanging flower pots. A small outdoor table and chairs are set on the gravel, inviting guests to enjoy the pleasant surroundings.

4.98 out of 5 average rating, 451 reviews

Stay in a piece of history! Private Entire Cottage

4.95 out of 5 average rating, 262 reviews

The exterior of The Storefront is displayed, showcasing a two-story, blue-painted building flanked by red brick structures. A striped awning is positioned over the entrance, and large windows provide a glimpse into the welcoming ambiance inside.

Flat in Staunton

The Storefront: Downtown Staunton + Unique Stay

4.96 out of 5 average rating, 107 reviews

An outdoor fire pit area is illuminated by string lights, providing a cozy gathering space. Several wooden chairs surround a rocky fire pit, with scenic views of the surrounding mountains visible in the background. The cabin is partially visible, set against a twilight sky.

Cabin in Afton

Log Cabin w/ Views! 8+ Acres! Pets!

4.97 out of 5 average rating, 117 reviews

A rustic log cabin is surrounded by lush greenery in a serene wooded setting. The spacious front lawn is fenced, providing a safe area for pets. The porch features a swing, inviting relaxation amidst the natural landscape.

Cabin in Madison

Relaxing 2BR CABIN, 12 acres, dog friendly, hiking