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Pet-friendly vacation rentals in Madison County

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Top-rated pet-friendly home rentals in Madison County

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
Home in Madison

Robinson River Retreat - Near River, SNP & Graves

Great location near the Blue Ridge Mountains in Madison County for family or friends. 3 BR, 2 BA spacious house. Property continues across street to the peaceful Robinson River for swimming or fishing. Minutes to scenic trails at White Oak Canyon/Cedar Run and Old Rag in Shenandoah National Park. Many wineries and breweries are near by as well as seasonal festivals at Graves Mountain Lodge. Convenient to Culpeper and Charlottesville. Fiber Internet with 140 Mbps upload & download; 30 ms Latency

4.93 out of 5 average rating, 150 reviews
Top guest favorite
A scenic view of a pond surrounded by open land and trees reveals a family enjoying the outdoors. Mountains are visible in the background, creating a peaceful and spacious setting. The landscape includes a small structure near the pond, contributing to the rural charm.
Home in Hood

Firnew Cottage

A perfect family getaway from the city in the heart of Virginia Wine Country, 15 min from Shenandoah National Park, 30 min from Charlottesville. Private cottage on 265 acres with 3 mi. hiking trail, overlooks 2 ponds/playhouse offers complete farm experience. Walk to swimming hole on river, canoe/fish in lake, feed peacocks/ goats, collect fresh eggs. Great sunsets. Fire-pit. Close to wineries, breweries, Montpelier, Monticello - only 1.5 hrs to DC/Richmond. Pet friendly. Tour included.

4.98 out of 5 average rating, 331 reviews
Guest favorite
An aerial view captures the surrounding countryside, featuring sprawling green fields and distant mountains under a partly cloudy sky. The image shows a mix of residential buildings, including cottages and a red-roofed structure, situated amidst lush trees.
Cottage in Madison

Robinson River Roost - Cottage near Shenandoah NP

Enjoy a slice of country life in our rustic 2 BR, 1.5 bath cottage nestled along the Blue Ridge in Madison County. Great for a family or small group. Minutes to scenic hikes at White Oak and Old Rag in Shenandoah National Park, plus wineries, breweries and festivals at Graves Mountain Lodge. Steps away from trout fishing and swimming holes of the peaceful Robinson River, plus Possum's Store across the street. Convenient to Charlottesville, Culpeper, Blue Ridge Pkwy, Luray Caverns, Camp Varsity.

4.91 out of 5 average rating, 195 reviews
Top guest favorite
A spacious living area is designed with wooden paneling and warm lighting. Comfortable seating, including a large cream sofa and armchairs, surrounds a central round coffee table. A patterned area rug covers the wooden floor, while a dining area and kitchen are visible in the background.
Cottage in Madison

Spectacular Mountain Retreat

Cottage is the guest house of our country home. Situated on a mountain with spectacular views of the Blue Ridge and access to many hiking trails; biking; fishing and swimming in private pond only steps from the door. Cottage is located within easy driving distance of multiple wineries, Sky Line Drive and Shenandoah National Park; Montpelier; and restaurants and shops. We can accommodate no more than one dog, with prior permission. In April 2023, we again upgraded our internet (see below).

4.93 out of 5 average rating, 106 reviews
Top guest favorite
A hot tub is positioned on a wooden deck, overlooking a scenic valley and distant mountains. The sky is filled with vibrant hues of orange and purple as the sun sets, creating a tranquil ambiance in this outdoor space.
Cabin in Stanley

New, 5BD/4BA | hot tub, arcade, pool table, views

Welcome to this new, 2,880 sf LUXE retreat in Shenandoah Woods--a spacious cabin designed for unforgettable getaways. It features 5 king beds, 4 full baths (2 en suite, 1 adjoining, 1 hall), and stunning views from the porches, hot tub, and rooms. More highlights: ★Arcade, board games, 6 ft pool table ★Fire pit ★Elect fireplace ★Elect Grill on deck ★Smart TVs up to 70" ★Fast WiFi ★Dining for 10 ★Well-equipped kitchen ★5 mins-Stanley ★13-15 mins-Luray Caverns ★25 mins-Shenandoah National Park

4.99 out of 5 average rating, 306 reviews
Top guest favorite
The log cabin exterior is highlighted by a stone chimney and a welcoming porch with steps leading to the entrance. Lush green trees surround the cabin, creating a serene atmosphere in the tranquil forest setting.
Cabin in Madison

Log Cabin at Ragged Rock Ridge

Mountaintop log cabin nestled in a mature, tranquil forest with spectacular views, ideally located near adventures like hiking in Shenandoah National Park (including Old Rag & White Oak Canyon), many local wineries/breweries/distilleries and quaint towns of Sperryville & Madison, VA. The authentic log cabin includes a cozy stone fireplace, porch, and patio with Old Rag views. Ponds, wildlife and hiking also available on the sprawling 300-acre property. Escape to the Cabin at Ragged Rock Ridge.

5.0 out of 5 average rating, 164 reviews
Guest favorite
A charming cottage is depicted with a sloped roof and a white exterior, surrounded by an expansive green field. The backdrop features rolling hills under a soft sunset sky, adding a serene ambiance to the setting.
Cottage in Leon

Comfy Cottage Near SNP, Hiking, & Wineries

This cottage at Grateful View is conveniently located in beautiful Madison Co. Accessible to Rt 29 and centrally located to local breweries, wineries (across from Prince Michel), and hiking. A few local places to visit include: Bald Top Brewing Company, Early Mountain Vineyard, the Skyline Drive in Shenandoah National Park (Old Rag Mtn and White Oak Falls). An easy 15-minute drive to Culpeper or 35-minute drive to Charlottesville with historical sites, restaurants, and antique shops not far.

4.95 out of 5 average rating, 118 reviews
Top guest favorite
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

Bring the whole fur family & enjoy precious time away from the hustle & bustle of everyday life. This updated cabin sits on 12.5 acres of mainly wooded land in the heart of the blue ridge- Madison County. Within 30 minutes of wineries, breweries, hiking, & Charlottesville! Boasting a primary loft bedroom w/ a queen bed and a bonus room w/ a full bed, this home away from home can comfortably sleep 4-5! Front porch swing & fenced yard for the pups to play. Guests can completely relax!

4.97 out of 5 average rating, 141 reviews
Top guest favorite
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.
Home in Montpelier Station

The Cottage At Liberty Mill Upgraded WI FI Pet $50

Brand new charming cabin with views of the Blue Ridge Mountains. Two bedrooms, Loft with 2 twin beds, two large bathrooms and a spacious common area. Exposed chestnut beams, working gas fireplace make this cabin a perfect getaway. All the amenities you could want. Located minutes from James Madisons' Montpelier, 5 minutes from Historic Orange, 30 minutes to Charlottesville, 20 minutes to Culpeper and less than 2 hours to Washington, DC. A loft area with 2 twin beds. Upgraded WIFI

4.93 out of 5 average rating, 572 reviews
Guest favorite
An open-plan kitchen and living area is showcased with wooden beams and large windows, allowing natural light to illuminate the space. A kitchenette features wooden cabinetry, a microwave, and a small dining bar with three tall stools. A rocking chair is positioned beside a window overlooking the woodland.
Farm stay in Brightwood

Robinson River Cabin - Tri Creek Farm

If you spend most of your career glued to a computer and other screens, this place is for you. TriCreek Farm is a place for you to disconnect, reboot, and fuel your soul. This riverfront cabin is situated on ~100 acres, over 1/2 mile of Robinson River frontage, with breathtaking views. There are creeks, fishing, and hiking trails to explore and enjoy. The cabin is located in Brightwood, Virginia, a small town located in Madison County between Culpeper and Charlottesville Virginia.

4.94 out of 5 average rating, 176 reviews
Top guest favorite
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

Renovated duplex in Madison, VA. Enjoy a peaceful setting, amazing views and convenient to wineries, wedding venues & hiking. SAUNA! Near Early Mtn Vineyards, Prince Michelle Winery, Yoder's Market, Bald Top Brewing & Plow & Hearth. A 30 min drive to Charlottesville, Shenandoah Nat. Park, Culpeper & Orange. Shopping, restaurants, breweries, antiquing, site seeing and more. *RENT ENTIRE HOME* - Inquire for our unit A & B combined rate. Dogs allowed-$30 fee.

4.95 out of 5 average rating, 489 reviews
Top guest favorite
The exterior of a two-story cottage is visible, featuring a welcoming porch. Large windows allow for natural light, and seating is arranged on the porch. Surrounding greenery and a gravel pathway add to the peaceful ambiance, with a gently sloped landscape in the background.
Barn in Boston

Pet Friendly Cottage on 21 acre farm

Enjoy the lovely, quiet setting on 21 acres. Newly renovated 2 story bank barn will be your home away from home. Soft, muted colors, zen feel. Come relax, hike, ride your bike, go wine and craft beer tasting, Copper Fox Distillery, has nice gin and bourbon if you prefer. Visit Luray Caverns and Shenandoah National Park, or shop at Sperryville gift shops, restaurants, antique markets and art galleries. Old Rag Mountain is only 20 minutes away!

5.0 out of 5 average rating, 135 reviews

Popular amenities for Madison County pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Top guest favorite
A charming farmhouse is set amidst lush greenery, featuring a welcoming front porch with rockers. Colorful blooming flowers line the path, leading to the entrance. The white exterior contrasts with the natural surroundings, while a stone pathway directs attention to the inviting structure.
Home in Syria

Finks-Johnson House on Strother Run

4.99 out of 5 average rating, 164 reviews
Top guest favorite
The farmhouse is illuminated in soft light under a vast night sky filled with stars, showcasing the Milky Way's brilliance. Surrounding trees gently frame the property, while the building's brick exterior stands in contrast to the dazzling nightscape.
Home in Luray

Modern Farmhouse near Shenandoah Nat'l Park + Lake

4.99 out of 5 average rating, 642 reviews
Top guest favorite
An aerial view captures the farmhouse nestled in a expansive landscape, surrounded by rolling hills and patches of trees. Vibrant autumn foliage adds earthy tones to the scenery, with fields stretching towards distant mountains under a clear sky.
Home in Woodville

Walnut Run Farm - Private & Quiet - Sperryville

4.88 out of 5 average rating, 203 reviews
Guest favorite
The farmhouse is depicted from an angle, showcasing its welcoming facade. Large windows are featured prominently, allowing for ample natural light. A grassy lawn surrounds the home, with a fire pit visible in front. The sky is filled with soft clouds during twilight.
Home in Stanardsville

Long Run Farm

4.9 out of 5 average rating, 287 reviews
Top guest favorite
A spacious outdoor area is bordered by gravel and features a firepit surrounded by four wooden chairs. In the background, rolling mountains and clear blue skies enhance the serene setting, inviting relaxation and outdoor gatherings.
Home in Luray

Serendipity Retreat

4.97 out of 5 average rating, 117 reviews
Guest favorite
A serene landscape is captured, featuring rolling green hills and a distant view of mountains. Trees in various hues surround the area, with a few farm buildings visible. The sky displays soft pastel shades as the sun sets, enhancing the peaceful ambiance of the property.
Home in Hood

Benji’s Getaway Shenandoah.

4.87 out of 5 average rating, 101 reviews
Top guest favorite
Three red Adirondack chairs are positioned in a grassy area overlooking a landscaped yard, with trees and bushes providing a natural backdrop. The soft glow of dusk casts a serene ambiance across the scene.
Home in Madison

Home with beautiful mountain and river views

5.0 out of 5 average rating, 92 reviews
Guest favorite
Home in Madison

Downtown Madison Studio near Hiking and Venues

4.91 out of 5 average rating, 74 reviews

Pet-friendly home rentals with a pool

Top guest favorite
An aerial view of the historic Woodbourne Estate Manor showcases its striking red roof and white facade. The surrounding landscape features lush greenery, expansive fields, and well-maintained gardens. Pathways are visible leading to the entrance, enhancing the inviting atmosphere of this picturesque estate.
Farm stay in Madison

Brewery Manor Sleeps 10 Hot Tub

4.96 out of 5 average rating, 136 reviews
Guest favorite
An aerial view of the property reveals a lush landscape, with five distinct buildings arranged around a central natural pool. The Robinson River flows nearby, and a swinging pedestrian bridge connects to the lush greenery, emphasizing the serene and spacious surroundings.
Home in Madison

The River House at the Swinging Bridge

4.94 out of 5 average rating, 100 reviewsA renovated 1920s farm cottage sits on expansive green lawns, surrounded by lush vegetation and distant hills. A wooden deck wraps around the front, providing outdoor seating space. The structure features a gabled roof and large windows that invite natural light.
Home in Syria

Pete's Farm Cottage - on Graves Mountain Farm

4.76 out of 5 average rating, 17 reviewsA charming two-story cottage is showcased, featuring a light-colored exterior with a covered porch. Lush green grass surrounds the house, along with well-maintained plants and trees. The serene landscape offers a peaceful atmosphere under a clear blue sky.
Cottage in Reva

AJ's House: Beautiful, Cozy, Renovated! 165/nt

4.79 out of 5 average rating, 42 reviews
Cottage in Syria

Blackwood - Valley of Rose River by the Blue Ridge

4.62 out of 5 average rating, 13 reviewsThe cabin, partially nestled among trees, features a wooden deck supported by sturdy columns. A shallow stone foundation is visible beneath the structure, while green foliage surrounds the area, offering a sense of tranquility and connection to nature.
Cottage in Syria

Wild Wind Cottage - On Robinson River Trout Stream

4.71 out of 5 average rating, 17 reviewsA friendly black cow is seen grazing near a rustic log cabin with a red metal roof. The cabin's porch is visible, surrounded by lush greenery and trees, creating a serene, rural atmosphere.
Cabin in Madison

Joanie's Place Cabin next to Shenendoah NP

4.5 out of 5 average rating, 4 reviewsA charming two-story farmhouse stands beneath a clear blue sky, showcasing white siding and a welcoming front porch. The surrounding greenery includes tall trees and shrubs, contributing to the serene rural setting. A paved pathway leads to the entrance, offering easy access.
Cottage in Syria

Boxwood Cottage - Shenandoah National Park

4.71 out of 5 average rating, 35 reviews

Private, pet-friendly home rentals

Guest favorite
The exterior of the country house showcases a rustic red façade complemented by a covered front porch. A welcoming entryway is flanked by lush greenery and a gravel driveway, evoking a serene rural atmosphere amid the surrounding trees.
Cabin in Reva

10-Acre Dog-Friendly House w Grill & Near Wineries

4.95 out of 5 average rating, 186 reviews
Top guest favorite
The log cabin exterior is showcased, featuring a welcoming front porch with wooden railings. Stairs lead up to the entrance, flanked by natural stone landscaping. Surrounding trees create a serene atmosphere, while warm lighting from the windows adds a cozy touch.
Guest suite in Reva

The Log Cabin at Ridgeview - Hiking, Wine, UVA

4.97 out of 5 average rating, 166 reviews
Guest favorite
Cottage in Orange

Private Fenced Yard for Dogs/Horses - 2BR Cottage

4.95 out of 5 average rating, 517 reviews
Top guest favorite
A modern yurt is showcased with a domed roof and wooden exterior, surrounded by a green lawn. The large windows offer views of the landscape, while a spacious porch extends around the front. Autumn foliage adds color to the background.
Cabin in Syria

⭐️Mongolian Yurt⭐️1100ft²⭐️Fire Pit⭐️Full Kitchen

4.96 out of 5 average rating, 333 reviews
Top guest favorite
A charming cottage features a red and yellow exterior with a welcoming front porch and steps leading to a bright red door. Vibrant yellow daffodils bloom in the foreground, adding a touch of spring to the serene country setting.
Cottage in Etlan

Amy's Place

4.98 out of 5 average rating, 209 reviews
Top guest favorite
The yurt is set against a starry night sky, surrounded by towering trees. A spacious deck leads to the yurt's entry, while warm light emanates from its windows. The scene showcases a natural ambiance highlighted by foliage and a gravel path leading to the entrance.
Yurt in Etlan

Peaceful Secluded Old Rag Retreat

4.96 out of 5 average rating, 270 reviews
Guest favorite
Chalet in Stanardsville

River Song Chalet - Private Retreat!

4.87 out of 5 average rating, 306 reviews
Top guest favorite
A spacious log cabin is situated among tall trees, showcasing a welcoming wrap-around deck with multiple entry points. The upper balcony features a railing and large windows, allowing natural light to fill the interior. The surrounding landscape displays vibrant autumn foliage.
Cabin in Etlan

Stay near Old Rag +White Oak Canyon—Cozy Log Cabin

5.0 out of 5 average rating, 119 reviews

Destinations to explore