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Places to stay near James Madison's Montpelier

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Top-rated vacation rentals near James Madison's Montpelier

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Guest favorite
The Ordinary is surrounded by a spacious lawn, framed by trees and greenery. A small outbuilding is visible to the left, while the house features a welcoming porch and a pitched roof. Natural light brightens the exterior, emphasizing its classic Virginia charm.
Home in Barboursville

Historic 1790 House Near Charlottesville

Originally a tavern built 1790 in the Williamsburg style, the Ordinary sits 6/10 mile off the main road--no other house in sight. 22 miles from Shenandoah National Park, convenient to local vineyards, the Ordinary is set on 650 acres in conservation easement; solar energy; generator in event of power outage; outdoor fire pit; 2 great fireplaces; wood provided by owner. The house is over 200 years old with narrow, steep steps and may not be suitable for children and people with mobility issues.

4.93 out of 5 average rating, 138 reviews
Top guest favorite
A newly constructed guesthouse features a charming exterior with a sloped red roof and white trim. A covered balcony with a red umbrella overlooks landscaped gardens. Stone pathways and greenery surround the home, enhancing the inviting outdoor space.
Guesthouse in Orange

Taj Garage Guesthouse

Above garage guesthouse with private, self check-in entrance, off-street parking, among historic homes, 4 blocks to restaurants, shops, park, etc. in downtown Orange. Includes a fully equipped kitchen, queen bed, full bath, seating area, TV, wifi and balcony. Custom heart pine furniture, EV charger, refrig, stove, microwave, toaster and Keurig. Close to superb wineries, breweries and historic sites. Four blocks from the railroad so you will occasionally hear "that lonesome whistle blow".

5.0 out of 5 average rating, 319 reviews
Guest favorite
A charming single-story house is presented with a light-colored exterior and dark shutters. Rocking chairs are positioned on the front porch, inviting relaxation. A well-maintained lawn surrounds the home, and a backdrop of trees complements the serene setting.
Cottage in Orange

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.

4.9 out of 5 average rating, 230 reviews
Top guest favorite
The entrance features double wooden doors that open to a welcoming interior. A 'hello' mat is placed on the threshold, and two stylish chairs are positioned on the balcony above, inviting guests to enjoy the view. Lush plants accentuate both sides of the entrance.
Apartment in Somerset

Cozy Farm Apt near Cville•hot tub, sauna, mt views

Come experience a relaxing getaway on our family’s dairy farm in Somerset. In beautiful Orange County, We are close enough to Charlottesville (25 min) for all your shopping and eating needs, but has the privacy, calm and tranquility of the country, with beautiful majestic mountain views! This is a wonderful location for exploring all of wine country, unwinding from the hustle of busy life, and then taking in the sunset in this quiet country setting with rolling hills as your backdrop!

4.98 out of 5 average rating, 224 reviews
Top guest favorite
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

4 unique rentals available (click our profile)! Unwind at this Central VA Country Paradise! Stay in a converted Barn & Silo w/ private natural swim pond and waterfall tucked into the woods on 140 Acres! Your own Oasis awaits, step out on your porch for coffee/drinks with the farm animals. Take a hike around the Lake on the 5+ miles of trails before cooling off in the pond while you gaze up at the stars. Sheep, Dwarf Fainting goats(next to silo 10' away), Chickens, Ducks, Bunnies, & Turkeys.

4.99 out of 5 average rating, 147 reviews
Top guest favorite
A charming green cottage is presented, featuring a small front porch with two chairs and potted flowers. Large windows allow natural light to fill the space, while the surrounding landscape includes grassy areas and trees, providing a peaceful rural setting.
Bungalow in Orange

Farm Cottage just outside town of Orange.

Charming 1920's cottage on a large farm just outside the town of Orange. Completely renovated and updated. Convenient to vineyards, battlefields, wedding venues and popular tourist destinations. Bucolic setting, very private. Spaces to enjoy the out of doors. Less than 2 miles to in-town wedding venues and Rounton Farm. Less than 4 miles to Inn at Willow Grove. 5 miles to Montpelier. Less than 7 miles to Grelen. 10 miles to Gordonsville. 12 miles to Barboursville. 19 miles to Mineral.

4.99 out of 5 average rating, 503 reviews
Top guest favorite
Cottage in Orange

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!

4.95 out of 5 average rating, 514 reviews
Top guest favorite
A view from an open doorway reveals a covered porch with white rocking chairs. A welcome mat lies on the wooden floor, leading to a scenic landscape of rolling hills adorned with autumn foliage. A glimpse of black chairs is visible in the distance.
Cottage in Gordonsville

Merry View Cottage

Our newly renovated farm cottage sits at the edge of a grove of giant hardwoods. Enjoy year round mountain views, including Merry Mountain. Ease into the morning while watching wildlife from a front porch rocker. Visit local wineries, breweries, restaurants, museums, shops, hiking trails or wedding venues. Unwind in the hammock or practice yoga on the back deck. Prepare dinner in our full size kitchen. Then, star gaze around the fire-pit after dark. This peaceful oasis awaits you.

5.0 out of 5 average rating, 213 reviews
Top guest favorite
A modern cabin-style home is nestled among tall trees, showcasing a sleek black exterior. A spacious screened-in porch is visible, supported by a deck with steps leading down to a gravel path. Large windows enhance the connection with the natural surroundings.
Home in Orange

Hidden Haven

Hidden Haven is just that! A 600 square foot romantic, private, peaceful, little haven. Hidden in the woods just 6 miles outside of the Town of Orange. Open the garage door in the living area and step out on the 300 square foot screened in porch where you can relax at the firepit under the covered roof. On the porch at Hidden Haven, we like to say, "time wasted is time well spent". The romantic vibe and modern amenities make it a prefect place for a couple's getaway.

4.97 out of 5 average rating, 199 reviews
Top guest favorite
Treehouse in Stanardsville

CloudPointe Retreat

Rare Appalachian Treehouse Gem! Luxurious, one-of-a-kind retreat for couples. Elevated tiny house among the treetops, private parking, plush bedroom, sleek bathroom, beautiful kitchenette, loveseat, lounge, private double-level decks, fireside lounging (wood provided), gas grill, and patio with a hot tub! Surrounded by nature, with wineries, hikes, restaurants and shopping all nearby. Please come and relax and revel in the beauty of nature! 4WD is recommended.

4.98 out of 5 average rating, 129 reviews
Top guest favorite
The cottage is set amidst lush greenery, showcasing a charming exterior with a light-colored facade and a metal roof. Adjacent to the porch, two rocking chairs frame the entrance, while neatly trimmed shrubs and vibrant flowers enhance the welcoming atmosphere.
Cottage in Orange

Cozy Country Cottage

"Cozy Country Cottage" is a rare find. It's located in a quiet neighborhood surrounded by beautiful farmland. It has a self check-in entrance, parking next to house and an amazing view of sheep grazing in pasture across the road. It's close to wineries, breweries, historic sites such as Mount Pelier, Monticello which is 23 miles, Woodberry Forest School which is 10 mins. away, shopping, hiking and more. Come and enjoy the quite, peaceful country !

4.94 out of 5 average rating, 101 reviews
Top guest favorite
The exterior of the home features a traditional two-story structure with white siding and blue shutters. A welcoming front porch is adorned with potted plants and a seasonal wreath. Lush greenery surrounds the entrance, leading to a stone pathway.
Home in Orange

Monrovia on Main

Monrovia on Main is a beautifully restored gem built in 1904. Guests have use of the entire 3,400 square foot, 5 bedroom home with 3 updated full baths. Enjoy a private backyard or front porch for morning coffee or evening drinks. Walking distance to an array of shops & restaurants in downtown Orange. The home is located near Montpelier, Woodberry Forest as well as Barboursville Vineyards.

4.98 out of 5 average rating, 135 reviews

Popular amenities for vacation rentals near James Madison's Montpelier

KitchenWifiPoolFree parking on premisesAir conditioning

Other top sights near James Madison's Montpelier

Carter Mountain Orchard

289 locals recommend

James Monroe's Highland

168 locals recommend

Jefferson Vineyards

121 locals recommend

Horton Vineyards

69 locals recommend

Eastwood Farm and Winery

44 locals recommend

DuCard Vineyards

112 locals recommend

Condo rentals with wifi

Top guest favorite
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.
Condo in North Downtown

The Townie 3 BD/2BA Historic Downtown Building

4.92 out of 5 average rating, 201 reviews
Superhost
A sunlit sunroom features large panoramic windows offering views of the outdoors. Comfortable seating is arranged with two wicker sofas and a daybed, accented by vibrant cushions and a decorative blanket. A coffee table sits in the center on a striped area rug.
Condo in North Downtown

Luxurious Posh Downtown Condo

4.91 out of 5 average rating, 193 reviews
Guest favorite
A series of ski gondolas are seen ascending a mountain, suspended from overhead cables. Snow-covered slopes can be observed below, with a bright blue sky providing a clear backdrop. The gondolas feature large windows, allowing views of the winter landscape.
Condo in McGaheysville

Massanutten Woodstone 2-BR, 2 Bath

4.84 out of 5 average rating, 147 reviews
Top guest favorite
A bright living room features two large sofas facing each other, complemented by a cozy chair. A coffee table sits between them atop hardwood flooring. A flat-screen TV is mounted on the wall opposite the seating. Light curtains frame the glass doors leading to a patio.
Condo in Mineral

First Floor Lake Anna Waterfront Condo + Boat Slip

4.97 out of 5 average rating, 29 reviews
Superhost
Condo in Charlottesville

Pet-Friendly in Belmont near UVA & Downtown - #311

5.0 out of 5 average rating, 3 reviews
Guest favorite
A scenic view of a waterfront area is captured, featuring a wooden dock with boat slips and a smooth path lined with rocks. Trees adorned in autumn colors frame the calm water, enhancing the peaceful atmosphere of the lakeside setting.
Condo in Mineral

Pet-Friendly Lake Anna Condo w/ Boat Slip

4.9 out of 5 average rating, 80 reviews
Superhost
An outdoor pool is showcased under a clear blue sky, surrounded by sun loungers and blue umbrellas. The water appears inviting, with gentle ripples reflecting the sunlight. Lush greenery is visible in the background, contributing to the serene setting.
Condo in Gordonsville

Beautiful 2BD condo in an equestrian themed resort

5.0 out of 5 average rating, 4 reviews
Guest favorite
A three-bedroom cabin is surrounded by tall trees, featuring a wooden exterior that blends with the natural environment. A set of stairs leads to a welcoming front porch, while a paved path guides visitors through the well-maintained landscape.
Condo in Gordonsville

Shenandoah 3BR Cabin on Lovely Resort w/amenities

5.0 out of 5 average rating, 8 reviews

Family-friendly house rentals

Top guest favorite
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

4.99 out of 5 average rating, 918 reviews
Guest favorite
A charming cottage is illuminated in the evening light, showcasing a welcoming entryway with yellow glow. The lawn is green and well-maintained, bordered by shrubs and trees, with a glimpse of outdoor seating visible near the entrance.
Home in Gordonsville

Wine Country Cottage, Hot Tub, Game Room, Slps 12

4.99 out of 5 average rating, 103 reviews
Guest favorite
An open living area features high wooden ceilings with exposed beams, creating a spacious atmosphere. A large kitchen island with bar seating is situated near a dining table. Two spiral staircases lead to upper levels, while large windows frame views of the surrounding nature.
Home in Robertson

One Of A Kind Home in VA Wine Country on 50 acres

4.93 out of 5 average rating, 258 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

4.98 out of 5 average rating, 329 reviews
Top guest favorite
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

4.96 out of 5 average rating, 359 reviews
Top guest favorite
A spacious game room is presented, featuring a billiard table, ping pong table, and foosball table, all situated on light-colored flooring. Well-lit by recessed ceiling lights, the room offers a contemporary feel with a dark accent wall adorned with textured paneling.
Home in Orange

Lake Anna Getaway • HotTub, GameRoom & Lake toys

4.99 out of 5 average rating, 132 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

4.95 out of 5 average rating, 488 reviews
Top guest favorite
Home in Charlottesville

Tranquil Estate Cottage | Vineyards & C'ville

4.95 out of 5 average rating, 745 reviews

Apartment rentals with air conditioning

Top guest favorite
Apartment in Rochelle

1 Bedroom Apartment With a Kitchenette on 28 Acres

4.92 out of 5 average rating, 217 reviews
Top guest favorite
A private hot tub is positioned on a wooden deck, inviting relaxation. The exterior of a two-story building is visible in the background, featuring a well-maintained lawn and a staircase leading to a covered porch. Soft lighting illuminates the outdoor seating area.
Apartment in Madison

The Studio at Dark Run Retreat

4.91 out of 5 average rating, 276 reviews
Top guest favorite
A vibrant sunset illuminates the sky with shades of orange and pink, casting a warm glow over the rolling hills. Lush greenery is visible in the foreground, complemented by scattered trees and shrubs, offering a serene view of the surrounding landscape.
Apartment in Stanardsville

Parker Mountain Carriage House Near SNP, UVA & JMU

4.97 out of 5 average rating, 237 reviews
Top guest favorite
A cozy living area is equipped with a vibrant yellow armchair and a light gray sectional sofa. A large screen TV is mounted on the wall, and natural light enters through a window adorned with white curtains. A round wooden coffee table sits on a patterned area rug.
Apartment in Culpeper

Red Fox Retreat

4.98 out of 5 average rating, 144 reviews
Top guest favorite
Apartment in Gordonsville

A private apartment with Self Check-in.

4.97 out of 5 average rating, 535 reviews
Guest favorite
The spacious living and dining area features a large dining table set with blue dishware. A comfortable seating area is arranged with a dark sofa facing a television. Natural light fills the room through expansive windows, highlighting the modern kitchen in the background.
Apartment in North Downtown

On Downtown Mall | Huge | King Beds | UVA | Coffee

4.94 out of 5 average rating, 197 reviews
Top guest favorite
Apartment in Crozet

The Barn at Haden near Wineries and C'ville

4.99 out of 5 average rating, 560 reviews
Guest favorite
An open-plan living space is featured, showcasing comfortable seating arrangements, including a beige sofa and dark chairs. A coffee table is positioned centrally, with a TV unit nearby. Light walls and warm lighting create an inviting atmosphere, complemented by a patterned area rug.
Apartment in North Downtown

*Private Apartment in Downtown Cville*

4.84 out of 5 average rating, 669 reviews

Other great vacation rentals near James Madison's Montpelier

Guest favorite
Farm stay in Rapidan

Iconic Farmhouse w/ Furnished Silo & Highland Cows

4.87 out of 5 average rating, 153 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

4.94 out of 5 average rating, 174 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

4.97 out of 5 average rating, 139 reviews
Guest favorite
The cottage features a distinctive red exterior with a green roof, set amidst lush greenery. A welcoming front porch is visible, with two chairs placed on it. The surroundings include trees and a clear blue sky, emphasizing a tranquil outdoor setting.
Cottage in Ruckersville

Lake Haven Cottage

4.89 out of 5 average rating, 390 reviews
Top guest favorite
Cabin in Stanley

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

4.99 out of 5 average rating, 301 reviews
Guest favorite
The exterior of La Petite Maison showcases a charming guest house with a large screened porch, surrounded by vibrant flower beds. A turquoise umbrella shades a lounge chair next to the seasonal in-ground pool, providing a relaxing outdoor space.
Guesthouse in Gordonsville

La Petite Maison at Hedgeapple Hollow

4.9 out of 5 average rating, 195 reviews
Guest favorite
A charming guest cottage is set amidst greenery, featuring a welcoming front porch with white railings. Stone steps lead to the entrance. An inviting garden surrounds the cottage, complemented by decorative landscaping and trees in the background, creating a serene outdoor environment.
Guesthouse in Gordonsville

Gordonsville Guest Cottage - private studio

4.95 out of 5 average rating, 120 reviews
Top guest favorite
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

4.99 out of 5 average rating, 245 reviews