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, 256 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!

The exterior of the West Wing showcases a welcoming entrance with a vibrant pink door. Steps lead up to the porch, which is surrounded by lush greenery and potted plants. The house's architecture features a combination of siding and a screened-in area, blending with the mature garden.

4.91 out of 5 average rating, 313 reviews

West Wing

Quiet West Wing of my home, was newly renovated February 2020. The West Wing has a private entrance set in a mature garden. Two bedrooms upstairs sleep up to four people. One w/queen size bed and views of the garden.The 2nd has 1 full and 1 twin bed, plus walkout balcony. Each floor has a full bath. The 1st floor has a combined living room/dining area with a counter, bar sink, microwave, coffee maker, toaster oven andTV. Pet dogs only are welcome. The cleaning fee is included in the base price

4.93 out of 5 average rating, 299 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

4.9 out of 5 average rating, 240 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.

4.99 out of 5 average rating, 149 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.

4.96 out of 5 average rating, 306 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*

Our Log Cabin has EVERYTHING you need for your mountain vacation! Miles of gorgeous mountain views off the large wrap around porch. *Outdoor Hot Tub *Indoor Wood Burning Fire Place *15 minutes from Shenandoah National Park *30+ Local Wineries!! *Outdoor Firepit *1GB WIFI and Huge TVs! *Close to UVA/ Charlottesville *Full Kitchen *Large, Private Deck with Mountain Views *Propane Grill *Outdoor Heater *Plenty of Space to Park Cars *Hiking *Maybelle's General Store less than a mile away

4.97 out of 5 average rating, 380 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!

4.98 out of 5 average rating, 121 reviews

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.

Home in Woolen Mills

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

4.99 out of 5 average rating, 211 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!

Cottage in Jefferson Park Avenue

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, 448 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.

4.95 out of 5 average rating, 440 reviews

Home in Woolen Mills

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.

A spacious living area displays soft beige sofas paired with dark blue accent tables. Natural light filters through large windows, enhancing the warm, neutral tones of the walls. A glimpse of the kitchen and bedroom can be seen through open doorways, providing a sense of flow.

4.96 out of 5 average rating, 215 reviews

Woodwind Cottage

Woodwind Cottage is a brand new, beautifully built cottage with living room, bedroom, bath, kitchen and loft. It has charming architectural details and a covered porch for enjoying the view of the woods. The loft has a fold out sofa for an extra guest or private work space. The home has wifi, smart tv for streaming, and a gas fireplace. Enjoy reading in the oversized window seat, rise early to see deer in the yard or, perhaps, a hot air balloon overhead in the spring and fall.

Popular amenities for Charlottesville pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A charming exterior of the home features a light brick facade with dark blue front door and large windows. The landscaped front yard contains neatly trimmed shrubs and natural stone pathways, leading to a welcoming entrance surrounded by tall trees that offer shade.

4.84 out of 5 average rating, 187 reviews

Peaceful and Spacious Woodland Haven Near UVA

4.8 out of 5 average rating, 157 reviews

The image showcases a weathered wooden sign featuring the name 'Massie-Wills House' along with 'ca 1830' inscribed in bold lettering. The sign's surface displays a faded tree design, emphasizing the historical significance of the location against a backdrop of red brick.

Home in North Downtown

Historic Cville Row House Steps from Downtown Mall

4.95 out of 5 average rating, 464 reviews

A welcoming entrance to the duplex is highlighted by a stone pathway leading to a wooden porch. Lush greenery surrounds the porch, with shrubs and trees providing a serene atmosphere. The sky is partially cloudy, adding to the tranquil outdoor setting.

Home in Madison

Unit A-Mountain Retreat- SAUNA-Hiking-Wineries

4.97 out of 5 average rating, 214 reviews

A charming white home features dark shutters and a bright yellow front door, framed by colorful foliage. Flags are displayed at the entrance, and a well-maintained lawn enhances the welcoming appearance. The path and landscaping lead to a warm invitation for guests.

Home in Crozet

Crozet Casa, Hot Tub, Fire Pit, Wine & Beer, PEACE

4.83 out of 5 average rating, 119 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

4.98 out of 5 average rating, 169 reviews

Spacious Victorian Suite on the Rivanna Trail

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, 553 reviews

The Cottage At Liberty Mill Upgraded WI FI Pet $50

The exterior of a brick house is framed by vibrant autumn foliage, with golden and orange leaves. A pathway of bricks leads to the entrance, and subtle landscaping includes a small tree displaying colorful leaves, contributing to a serene outdoor setting.

4.95 out of 5 average rating, 104 reviews

Spacious apt/near Charlottesville /UVA/wineries

Pet-friendly home rentals with a pool

4.94 out of 5 average rating, 154 reviews

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.

Home in Afton

Farmhouse on Working Vineyard

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, 796 reviews

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

4.99 out of 5 average rating, 133 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

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, 149 reviews

Bear's Mountain Escape

4.95 out of 5 average rating, 481 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

4.98 out of 5 average rating, 221 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!

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, 133 reviews

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10

4.81 out of 5 average rating, 118 reviews

A single-story house with white vinyl siding is surrounded by well-maintained greenery. A front porch features a swing, while large windows invite ample natural light. The muted color palette of the exterior harmonizes with the inviting lawn space, creating a peaceful outdoor setting.

Home in Schuyler

Peaceful Cottage

Private, pet-friendly home rentals

4.91 out of 5 average rating, 658 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

4.78 out of 5 average rating, 302 reviews

An open concept living area showcases wooden beams and heart pine floors. A cozy armchair with a floral pattern introduces color, while a desk and chair provide a workspace. The kitchen area features stainless steel appliances and an inviting countertop, fostering a warm communal space.

Flat in Fifeville

Classy new renovation in Fifeville

Guest suite in Charlottesville

A cozy sleeping area features a full-size bed dressed in a soft blue duvet with various decorative pillows. Warm lighting is provided by lamps on either side, and framed artwork adorns the wall above the bed, enhancing the inviting ambiance.

4.98 out of 5 average rating, 292 reviews

Private Basement Suite

4.95 out of 5 average rating, 337 reviews

A bright kitchen and dining area features wooden cabinets and appliances, including a microwave and refrigerator. A table with floral tablecloth is surrounded by four wooden chairs. Natural light enters through a nearby window, enhancing the warm atmosphere of the open space.

Farm stay in Free Union

Secluded Private Apartment - Pets Welcome!

4.95 out of 5 average rating, 102 reviews

An aerial view of Park Line Retreat reveals a cozy cabin surrounded by trees, with softly glowing string lights outlining a spacious deck. A private hot tub is situated nearby, enhancing the retreat’s inviting ambiance. Fire pit seating is visible along the path leading to the cabin.

Cabin in Stanley

ParkLine: Hot Tub, Outdoor Movies and firepit

4.99 out of 5 average rating, 168 reviews

A tranquil pond reflects the grassy landscape and the farmhouse, which features a welcoming front porch. A small boat rests on the water's edge, surrounded by greenery, creating a serene outdoor setting.

Farm stay in Louisa

Golden Meadows a Pet-Friendly Country Farm House

Apartment in North Downtown

A bright bedroom features a spacious bed flanked by two bedside tables with lamps. A framed cityscape artwork adorns the wall above the bed. Dark curtains frame the window, and a patterned rug covers the hardwood floor, creating a cozy yet modern ambiance.

4.91 out of 5 average rating, 179 reviews

The Townie 3 BD/2BA Historic Downtown Building