Pet-friendly holiday rentals in Charlottesville

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, 273 reviews

Ultimate cabin in the mountains

This unique and secluded cabin sits on 75 acres in the Blue Ridge mountains. Enjoy the cozy wood fireplace, hot tub, charcoal grill, and fast, reliable fiberoptic internet if you need to get some work done while you're away. It has a washer and dryer, a full kitchen, and is pet-friendly (no pet fee!), so you can enjoy it with the whole family. There is a 4K 55” smart TV with apps, a Tesla LVL 2 charger, a cabinet full of board games, books, and plenty of items to entertain both kids and adults!

PetsWalkabilityHospitality

4.93 out of 5 average rating, 311 reviews

A charming cottage with a metal roof features a welcoming front porch, surrounded by greenery. Rocking chairs offer a cozy spot, while stone pathways lead to a landscaped yard. Light spills onto the deck from nearby trees, blending indoor and outdoor spaces harmoniously.

Home in Barboursville

Spaniel Hill; cozy hilltop home w privacy & views

Cozy hilltop with Views, deck and hot tub. Cottage furnished with original art and antiques collected by us, the cottage is easy to get to but feels like a world away. Recently renovated main level has three cozy bedrooms and 1.5 baths, sleeps 6, and the garden level suite offers one large king bed and a twin bed with full bath and separate sink area, sleeps 3. Close to UVA, Pantops 250 corridor, theDowntown Mall, Gordonsville and Orange to our north. Over 20 highly rated wineries within 20 m

WalkabilityPetsHospitality

4.89 out of 5 average rating, 258 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.

Outdoor spacesWalkabilityCleanliness

4.99 out of 5 average rating, 162 reviews

A firepit area features several Adirondack chairs arranged around a sandy circle. Natural rock formations and a lush tree line create a serene backdrop, framed by expansive mountain views in the distance.

Chalet in Afton

Elk Mountain Overlook: Breathtaking Views

Mountaintop overlook with jaw dropping views and camp themed interior design. Perched upon Elk Mountain just off the Blue Ridge Parkway this petite chalet is under 30 min from Charlottesville, 10 min to 151 vineyards/breweries/cideries, and 10 min to Waynesboro. Relax in this natural retreat featuring 2 king bedrooms, 2 person soaker tub, double headed shower, and ample kitchen w/many extras. Take in the views from the large deck, firepit, under porch swing, or mountainside adirondack chairs.

Outdoor spacesWalkabilityComfort

4.99 out of 5 average rating, 154 reviews

Downtown Retreat | Fenced Yard + Pets Welcome

Peaceful North Downtown retreat just minutes from UVA, Downtown Charlottesville, Martha Jefferson Hospital, Virginia’s Wine Trail, and the Blue Ridge Mountains. This bright, single-level, pet-friendly home sleeps up to five guests and features a private fenced backyard with a fire pit and grill, a fully equipped kitchen, high-speed Wi-Fi, and a newly renovated spa-inspired bathroom. Whether you’re visiting for a UVA weekend, wine tasting, work, or a relaxing getaway, you’ll feel right at home.

Outdoor spacesPetsFamily

4.97 out of 5 average rating, 395 reviews

The image features a charming two-story home surrounded by lush greenery and flowering trees. A circular driveway leads to the entrance, with manicured lawns enhancing the exterior. The backdrop includes rolling hills and bright blue skies, creating a serene and inviting setting.

Home in North Garden

Lux Country Retreat minutes from Charlottesville!

Located just off route 29 this private luxury retreat with surrounding 2 acre fenced yard is one mile from Pippin Hill Farm & Vineyard and only 15 minutes from UVA/Charlottesville. You will find this home spacious, bright and airy, perfect for entertaining groups or families. The house is completely equipped with everything you may need to host the perfect getaway! Nearby attractions: Pippin Hill, Albemarle Ciderworks, Ragged Branch Distillery, Potter's Craft Cider and Charlottesville!

Outdoor spacesPetsLocation

A single-story home with light blue siding is set against a clear sky. A vibrant door adds a pop of color to the entrance, which is framed by landscaped flower beds. A paved walkway leads up from the driveway, inviting visitors towards the front entrance.

4.98 out of 5 average rating, 152 reviews

3BR / Pets Welcome / Fenced Yard / Fiber Internet

Sitting atop the neighborhood, Monticello can be seen from our Ridgetop home. Convenient to all parts of Charlottesville, including Downtown, UVA, and Hospitals. Local parks offer swimming, boating, & are all walkable. The fenced yard allows for a safe space for dogs and the private patio is perfect for relaxing. The home offers an open design in the kitchen, living & dining room. Bath has a modern tile with a jacuzzi tub. Fast TING fiber internet. Freshly painted. Big Green Egg grill

PetsOutdoor spacesHot tub

4.99 out of 5 average rating, 238 reviews

The dark wooden cabin, framed by lush greenery, sits at a hillside location with panoramic mountain views. A deck extends from the cabin, featuring a hanging basket chair. A warm sunset casts a golden hue across the sky, enhancing the serene atmosphere.

Cabin in Free Union

Shenandoah Stargazer with Sauna

Stargazer is the perfect place to get away from it all! The stillness and serenity of being nestled in a bird and wildlife sanctuary is so good for your soul. Watch the sunrise from a hanging basket chair at 2700 feet of elevation, or wait for moonrise and toast spectacular star views! Relax in the sauna after a day filled with hiking and an al fresco meal on the deck. Roast s’mores at the deck fire table or over the side yard fire pit. There's magic in the air at this mountaintop retreat!

Outdoor spacesPetsNearby

Cottage in Charlottesville

The exterior of a charming cottage is featured, showcasing white brick walls and a sloped gray roof. Two dormer windows enhance the appearance, while a welcoming red door serves as a focal point. Well-maintained green grass and manicured shrubs surround the house, creating a friendly environment.

4.91 out of 5 average rating, 455 reviews

Adorable cottage steps from Grounds

A cozy Milton Grigg designed cottage and detached carriage house three minutes walk to the Lawn and ten minutes walk to the Stadium. Nestled in a wooded neighborhood. Perfect for visiting parents, UVA chapel weddings, med student rotations, and football games. NOTE: The cottage sleeps five adults and the carriage house two adults. There is one bathroom in the cottage and one in the carriage house. Please read through all the information in the 'Description' section below before booking.

PetsWalkabilityQuiet

4.94 out of 5 average rating, 461 reviews

Walk DT | Pets | Soaking Tub | Parking

The High‑Note Craftsman Cottage – live like a local in downtown Charlottesville Stay in a charming and pet friendly Craftsman cottage just minutes from Charlottesville’s Downtown Mall. Enjoy a soaking tub, fast Ting fiber Wi-Fi, and rare free parking — perfect for couples, families, and remote work travelers. This bright, comfortable home blends historic character with modern amenities, creating the ideal base for exploring Charlottesville, UVA, wineries, and the Blue Ridge Mountains.

PetsWalkabilityNearby

4.95 out of 5 average rating, 182 reviews

The exterior of a lakeside log cabin showcases a large, sloped roof with wooden beams and expansive windows. A spacious deck is visible, featuring various seating options. The structure combines natural stone and wood elements, reflecting a rustic yet modern aesthetic.

Cabin in Faber

Lakefront Cabin w Stunning Curated Decor & Hot Tub

✨ A Marvelous Night for a Moondance Awaits ✨ Welcome to Moondance—a lakeside log cabin with serious style and mountain soul. Designer interiors, cozy fireplaces, an après-ski game room, and dreamy views set the stage. Whether you're sipping wine on the deck or roasting s’mores under string lights, this is where memories are made. Minutes to wineries, Wintergreen, and the Blue Ridge Parkway. Relax, reconnect, and maybe do nothing at all. We support that.

Outdoor spacesWalkabilityNearby

4.97 out of 5 average rating, 166 reviews

A modern cabin exterior is showcased, designed with large windows and a wood facade. A spacious deck features seating and a dining table, surrounded by lush greenery. The cabin is elevated above the ground, blending harmoniously with the natural landscape.

Cabin in Stanley

The Gramophone - Romantic Valley Retreat

A Shenandoah Valley peaceful retreat in its own mini-valley, featuring a mountain-top creek rushing through the 3-acre property. Enjoy a romantic getaway with a premium sound system and record player, a wood-burning indoor fireplace, a wood-burning outdoor hot tub, a deck hanging among the trees, and tons of nearby adventures. These are just some wonders you can soak up during your stay. Just 2 hours away from Washington DC. Welcome to The Gramophone.

PetsWalkabilityDecor

Popular amenities for Charlottesville pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.96 out of 5 average rating, 357 reviews

A spacious, two-story house with white siding and large porches is featured. Lush green grass surrounds the structure, and the landscape includes open pastures and trees. The setting is serene, with plenty of natural light illuminating the exterior.

Home in Dyke

Living Water Farm, Blue Ridge

Outdoor spacesPetsAmenities

4.82 out of 5 average rating, 130 reviews

A modern chef's kitchen is showcased with a long white concrete countertop and an array of kitchen appliances. Underneath the countertop, a wooden shelf is filled with books. Adjacent to the kitchen, a dining area features a table surrounded by colorful chairs.

Home in North Downtown

Downtown Mall Architecturally Designed House

WalkabilityPetsValue

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.

4.97 out of 5 average rating, 124 reviews

Perfect getaway among the orchards of Batesville

PetsOutdoor spacesQuiet

4.96 out of 5 average rating, 384 reviews

The Brew Ridge Trail's Most Unique Home. Sleeps 12

WalkabilityPetsDecor

4.91 out of 5 average rating, 133 reviews

Group Retreat | Game Rm + 5 Min to UVA & Hospital

WalkabilityOutdoor spacesCondition

Home in Montpelier Station

A charming cabin with light-colored wood siding is set against a snowy landscape. A welcoming wreath adorns the front door. The surrounding area features tall trees blanketed in white snow, with steps leading up to the porch where a rocking chair is placed.

4.93 out of 5 average rating, 568 reviews

The Cottage At Liberty Mill Upgraded WI FI Pet $50

WalkabilityPetsBack garden

The two-story house features a white exterior with dark shutters and a welcoming front porch. A gently sloped lawn surrounds the home, leading to mature trees and a scenic backdrop. The roof is accented with three gabled dormer windows, adding character to the facade.

4.98 out of 5 average rating, 191 reviews

Clean family-friendly 5br for wine country getaway

Outdoor spacesWalkabilityLocation

4.92 out of 5 average rating, 119 reviews

Charlottesville Bungalow close to UVA

PetsOutdoor spacesDecor

Pet-friendly home rentals with a pool

4.88 out of 5 average rating, 381 reviews

A charming bungalow is framed by large trees and lush greenery, creating a serene outdoor setting. The white exterior features black shutters and flower boxes, while a welcoming front door is positioned at the center. A wooden fence and natural landscape complete the tranquil atmosphere.

Cabin in Gordonsville

18th Century Historic Charming Bungalow#127 & Pool

PetsOutdoor spacesDecor

A functional kitchen with wooden cabinetry and an island is featured. The space includes a stove, modern appliances, and a ceiling fan. A brick wood stove adds a rustic element, while a small plant sits on the island, providing a touch of greenery.

4.94 out of 5 average rating, 161 reviews

Farmhouse on Working Vineyard

PetsWalkabilityBack garden

Farm stay in Stanardsville

4.92 out of 5 average rating, 819 reviews

Airstream*POOL*PrivateTub*MTN*relax*GOATS*stars

Outdoor spacesPetsBeach

4.99 out of 5 average rating, 146 reviews

The exterior of the converted barn and silo is softly illuminated by string lights at dusk. A serene pond, framed by smooth stones, reflects the warm glow of light. The porch invites relaxation with its spacious seating and rustic charm, creating a peaceful outdoor setting.

Barn in Louisa

Unique OASIS - Silo Barn - Swim Pond- 5 Miles Trai

WalkabilityPetsQuiet

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.

4.95 out of 5 average rating, 167 reviews

Bear's Mountain Escape

WalkabilityOutdoor spacesCondition

4.95 out of 5 average rating, 506 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

WalkabilityOutdoor spacesGrill

4.98 out of 5 average rating, 229 reviews

A bright and airy living area is highlighted by large windows offering mountain views. A casual seating arrangement features a light-colored sofa and a wooden dining table surrounded by black chairs. Sliding glass doors provide access to an outdoor deck.

Flat in Rockfish

Blue Ridge Bliss - For family & friends to enjoy!

Outdoor spacesPetsWifi

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, 146 reviews

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10

PetsWalkabilityComfort

Private, pet-friendly home rentals

4.92 out of 5 average rating, 398 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!

PetsOutdoor spacesHeating

4.99 out of 5 average rating, 280 reviews

Treehouse in Verona

The Laurel Hill Treehouse

Outdoor spacesPetsQuiet

Bungalow in Charlottesville

The entrance features a welcoming red door framed by lush greenery. Stairs lead up to a covered porch adorned with a ceiling fan. Potted plants are arranged along the steps, contributing to the inviting atmosphere of the home.

4.89 out of 5 average rating, 532 reviews

Do Drop Inn - charming 2BR bungalow

PetsOutdoor spacesWifi

4.96 out of 5 average rating, 109 reviews

Cabin in Culpeper

Bison Farm - Cabin "Cielo"

PetsOutdoor spacesNearby

Cottage in Charlottesville

The exterior of a renovated home is visible, featuring a covered front porch with seating and a white front door. Lush greenery surrounds the house, enhancing the view of the neatly landscaped lawn and paved pathway leading to the entrance.

4.93 out of 5 average rating, 255 reviews

Woolen Mills Cottage- 2 Beds, 1 Bath, Full Kitchen

WalkabilityOutdoor spacesSleep quality

Farm stay in Charlottesville

A beautiful farm landscape is displayed, featuring lush green fields bordered by white fencing. Rolling hills extend into the distance under a bright blue sky, with scattered clouds overhead. Several buildings are set amidst the greenery, contributing to the tranquil rural atmosphere.

4.94 out of 5 average rating, 100 reviews

Cowboy cottage-hot tub on farm close to everything

Outdoor spacesPetsBack garden

4.96 out of 5 average rating, 324 reviews

A rustic log cabin is surrounded by lush greenery, featuring a large wrap-around porch with multiple access points. A stone chimney rises from the side of the building. Soft lighting emanates from the windows, highlighting the natural wood structure.

Cabin in Dyke

Shenandoah Getaway Cabin on 5 Acres w/ *Hot Tub*

PetsOutdoor spacesComfort