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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Top guest favorite

A charming cottage is set amidst a spacious green lawn, surrounded by trees. A hammock is visible in the foreground, suggesting a peaceful spot for relaxation. The building features a pitched roof and a cozy terrace area, with parking space for vehicles nearby.

Home in Hood

4.98 out of 5 average rating, 289 reviews

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.

Guest favorite

A snow-covered landscape is visible, featuring a black dog playing in the foreground. In the distance, a red barn is situated among the trees and rolling hills, with wooden fences outlining the property. The serene scene hints at peaceful surroundings.

Farm stay in Sperryville

4.98 out of 5 average rating, 130 reviews

The Roost at Upper Nonesuch

New for fall: Pickleball Court!. Located in the foothills of the Blue Ridge Mountains, Upper Nonesuch is the perfect place to get away and relax. Enjoy the serene view of the valley and rolling hills from the large screened-in porch and bedroom, the walking trails, the spring-fed pond on the adjacent farm. Take a short drive and enjoy hiking Old Rag and White Oak Canyon Falls. Explore Sperryville and Culpeper, the many orchards, wineries, breweries, all the Shenandoah Valley has to offer.

Top guest favorite

The log cabin is surrounded by mature trees and lush greenery, showcasing a well-maintained lawn. A stone chimney rises from the corner of the building, and wooden steps lead up to the cabin entrance, inviting guests into this tranquil woodland retreat.

Cabin in Madison

5 out of 5 average rating, 150 reviews

Log Cabin and 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.

Guest favorite

A front porch features two black rocking chairs positioned beside a small table adorned with flowers. The view beyond shows a spacious yard with a fence and horses grazing in the distance, framed by trees under a clear sky.

Cottage in Orange

4.9 out of 5 average rating, 170 reviews

Willie's Place Country Cottage Pets Allowed

Step out your front door and pet horses located next door. Willie's place is newly renovated and has all the amenities you need. Located close to wineries, shopping, wedding venues, Historic Montpelier, Corn Maze, Town of Orange, Woodberry Forest School, 10 minutes to Gordonsville, 30 minutes to Charlottesville. Kayak the Rapidan, take a horseback ride at Oakland Heights or see a play at Barboursville. Exposed beams throughout, a beautiful Loft and back porch for sitting. You won't go wrong.

Top guest favorite

A charming log cabin is set amidst a wooded area, featuring a spacious deck with a wooden railing. The screened-in porch offers a shaded area for relaxation, while the main entrance is visible from the yard, contributing to the cabin's cozy aesthetic.

Guest suite in Reva

4.96 out of 5 average rating, 118 reviews

The Log Cabin at Ridgeview - Hiking, Wine, UVA

Entire main floor of quaint log cabin in the heart of Virginia's Wine Country. Close to Charlottesville airport, UVa campus, Shenandoah National Park, wineries, breweries, local restaurants. NOTE: Prices shown are for 2 bedrooms, 1 queen and 1 double, and 2 baths. For access to 3rd bedroom, at an additional fee which includes one double and one single, set number of guests to 5 or 6. Access to laundry. Cozy front porch, tons of parking, screened in porch out back for dining or relaxing.

Top guest favorite

A covered porch features a glider and two chairs positioned on a wooden floor. Lush greenery and vibrant pink flowers enhance the natural surroundings visible through the railing, offering a peaceful outdoor seating area.

Guesthouse in Syria

4.96 out of 5 average rating, 380 reviews

Little House on Strother Run

Nestled between Mount Tom and Double Top Mountain and at the edge of the Shenandoah National Forest, Little House is the perfect starting out and ending point for a peaceful and relaxing stay in the Appalachian Mountains. Little House is located at the edge of our 7 acre property. You'll enjoy the bucolic atmosphere of our farmette which includes use of our shared sitting area on Strother Run. The sitting area is shared with the main house which is rented or used by our family periodically.

Guest favorite

A rustic red cabin is shown with a wooden porch and a grill. Large windows allow natural light to enter. The surrounding area features dried grass and trees, while a patio chair is positioned near the cabin, inviting relaxation in the outdoor space.

Tiny home in Reva

4.96 out of 5 average rating, 137 reviews

The Tool Shed, Pet Friendly

The Tool Shed at Mountain Field Farm provides a delightful retreat just a short 20-minute drive from the majestic Old Rag Mountain and the serene White Oak Falls. Immerse yourself in the breathtaking landscape, explore the nearby exquisite wineries and craft breweries, and meander through the quaint streets of Culpeper, where adventure blends seamlessly with relaxation and fine dining. Don’t forget to bring along some peppermints for our gentle horses, who are always eager to greet visitors.

Superhost

A compact cabin is showcased amidst tall trees, featuring dark wooden siding and large windows. Steps lead to a picnic table in the foreground, while a parked vehicle is seen nearby, indicating a private outdoor space perfect for relaxation.

Cabin in Stanardsville

4.87 out of 5 average rating, 727 reviews

Postcard Cabins Shenandoah - DC

An easy drive from the city, Postcard Cabins, formerly Getaway, is the ultimate way to experience the great outdoors. Nestled across acres of private woodlands, our tiny cabins have everything you need (AC/Heat, en-suite bathroom, fresh linens) and nothing you don’t. Featuring a private outdoor area (hello, fire pit), each cabin is designed to help you disconnect from the everyday. As part of your stay, you'll receive a complimentary allocation of provisions, like s’mores, coffee and more.*

Top guest favorite

A living area features a comfortable gray sofa and armchair, set on a light area rug. A wooden coffee table is centrally located, while a TV sits on a decorative stand. Natural light enters through a window, complemented by soft lighting from a chandelier above.

Cottage in Orange

4.96 out of 5 average rating, 431 reviews

Private Fenced Yard for Dogs/Horses - 2BR Cottage

2BR Hen and Hound Cottage is located just outside Orange, VA and has a private fenced yard for pets and walk-in access to adjacent James Madison's Montpelier and its many walking trails. In addition, we are minutes away from all of the popular wedding venues in Orange and a short drive to Shenandoah National Park. Our house on Whistle Stop Farm (so named for the train that passes by) is next to the cottage if you need us. Otherwise, the place is yours. Come enjoy some time in country!

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

4.96 out of 5 average rating, 406 reviews

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! On-site walking trail. 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.

Guest favorite

A cabin is illuminated warmly against a starry night sky, surrounded by tall trees with sparse foliage. The screened-in porch features large windows, reflecting the evening light. The landscape creates a serene and secluded atmosphere, inviting guests to connect with nature.

Cabin in Etlan

4.97 out of 5 average rating, 229 reviews

Modern Cabin | Old Rag in Shenandoah National Park

Stay near the best mountain trails in Shenandoah National Park with a few wineries and breweries close by. You'll have access to ... -- Our private creek and swimming hole -- A hot tub under the stars -- Starlink WiFi with up to 200 Mbps download speeds, adequate for remote work and streaming services (see more below) -- A kitchen fully stocked with all the equipment you'll need to prepare your own meals -- 2 bedrooms and an inflatable mattress in the common area

Guest favorite

The image depicts a scenic view of a rural property featuring two red barns in the background and a single-story cottage in the foreground. Lush green landscaping surrounds the structures, with parking visible and distant hills framing the scene under a soft, overcast sky.

Barn in Etlan

4.97 out of 5 average rating, 173 reviews

Hayloft Cottage

The Hayloft Cottage is open year-round for your country-living pleasure. Spring is here! This is your chance to get away from all the crowds and spend some peaceful down-time in your own, personal retreat. Enjoy the many local hiking trails, the fields, the mountains, and the fresh air. And feel free to bring the pups along (dogs only; limit 2). We have a fenced-in, 1.5 acre lot shared with our other cottage (Amy's Place) and ourselves.