Vacation rentals in Dillwyn

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Top-rated vacation rentals in Dillwyn

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A charming cottage is nestled among lush green grass and surrounded by trees. Its metal roof and white siding are complemented by well-maintained shrubbery. Dappled sunlight filters through the tree branches, creating a serene outdoor ambiance.
Cottage in Covesville
5 out of 5 average rating, 157 reviews

Historic cottage with stunning mountain views

Welcome to Rose Cottage in picturesque Albemarle County, where you'll enjoy expansive 360-degree views of the mountains surrounding historic Cove Lawn Farm. Relax in the tranquil rural setting or stroll more than two miles of comfortable walking paths that wind through 25 acres of stream-lined hayfields. From Rose Cottage, you're just minutes from the best local cideries, distilleries, and wineries including Pippin Hill Farm & Vineyards. Easy 20-minute drive to UVa and 22 minutes to Monticello.

Top guest favorite
The exterior of the log cabin is highlighted by a blend of natural wood and green metal roofing. Lush greenery surrounds the house, with vibrant pink flowers adding a touch of color. Windows maintain a classic design, framed in white, complementing the cabin's rustic charm.
Cabin in Farmville
4.98 out of 5 average rating, 133 reviews

Caryn’s Cozy Cabin Hampden-Sydney

Beautifully restored spacious and peaceful log cabin with curated finishes, furniture, and fixtures throughout. Kitchen layout, along with adjoining sunroom and deck are perfect for family gatherings. Incredible location. Less than 4 miles from Hampden-Sydney, Longwood University, Downtown Farmville, Appomattox River, High Bridge Trail, and Dining Shopping. 4 bedrooms -2 queen beds and 4 twin- 3 full bathrooms. Central air, fireplace, WiFi, 3 TVs, and washer and dryer. Managed locally

Top guest favorite
A gravel driveway leads toward a scenic countryside view, framed by trees on either side. At the entrance, two large tree stumps stand prominently, while a mailbox and a signpost indicate the property location. A soft sunset glow is visible in the distance.
Home in Farmville
5 out of 5 average rating, 132 reviews

The Hide-A-Way

Follow a long gravel driveway before you can view this comfortable house in the country. This house is 12 easy miles from the Town of Farmville and all it has to offer. Longwood University and Hampden-Sydney College is near by. Visit High Bridge State Park for hiking and Greenfront is a shopping destination. Lots of dining options will appeal to every taste and plenty of other activities to enjoy in this area. There is no phone-internet or satellite at The Hide-A-Way, Cell phones do work.

Top guest favorite
The cottage exterior is seen with a spacious front porch featuring two rockers and small tables. A warm glow from lights illuminates the entrance. The building showcases a sloped metal roof, charming green shutters, and potted plants on either side of the door.
Cottage in Scottsville
4.99 out of 5 average rating, 135 reviews

The Cottage at Hardware Hills Vineyard

Head for the Hills! The Cottage at Hardware Hills Vineyard sits atop the property alongside the main estate house. Bask in Virginia sunsets over the vines. Take a short hike down to the Hardware River where you can dip a toe in or try your hand at fishing. On weekends, you have a family-owned winery right in your front yard to stroll down and sit by the vines to enjoy delicious wines. Centrally located to many wine trail attractions and all that the Charlottesville area has to offer.

Top guest favorite
A circular firepit made of natural stones is surrounded by a gravel and mulch base, with a crackling fire at its center. The rustic cabin with a metal roof and large windows can be seen in the background, framed by lush greenery.
Home in Farmville
4.92 out of 5 average rating, 236 reviews

The Inn at Hampden-Sydney

A peaceful, quiet, and cozy home on 36 acres of beautiful land that rests just 5 minutes from Hampden-Sydney College and 10 minutes from Longwood University. We want your stay to be comfortable and relaxing, which is why each bed is comfortable and topped with luxurious linens. The house is equipped with 3 big screen tv's. You can also watch the deer from the enclosed front porch or open back deck. Enjoying sitting around the firepit or walking along one of the many paths on the property.

Guest favorite
Cabin in Farmville
4.97 out of 5 average rating, 189 reviews

Cedar Ridge Lodge | Hot Tub + Fire + Trail Access

Gather your crew and escape to Cedar Ridge Lodge! A timber-frame log lodge tucked into 27 private wooded acres in Virginia, just 3 hrs from DC and 1 hr from Richmond. Spend your days biking/hiking High Bridge Trail, your evenings around the fire ring, and your nights soaking in the private hot tub on the wrap-around porch. Wood-burning fireplace, game loft with board games, full kitchen, and WiFi when you need it. Downtown Farmville is just minutes away. Come relax and unwind!

Guest favorite
A vibrant sunset casts shades of orange and pink across a panoramic view of rolling hills and valleys. Lush trees frame the scene, while distant mountains create a serene backdrop against the colorful sky, embodying the tranquility of the surrounding landscape.
Cabin in Buckingham
4.94 out of 5 average rating, 191 reviews

Lotus View Retreat in Yogaville/Chalet

Custom-Built Retreat with Breathtaking Views This beautifully custom-built, fully furnished 2-bedroom home offers stunning panoramic views of the James River, Lotus Temple, and Blue Ridge Mountains, all just one mile from the heart of Yogaville. Nestled in peaceful seclusion, this standalone home features a private wraparound deck, a grand great room with soaring cathedral ceilings, and a serene master bedroom with an en-suite bathroom—a perfect sanctuary for relaxation.

Guest favorite
A two-story home is nestled among lush greenery, featuring a wooden exterior and a sloped roof. A small structure resembling a playhouse is positioned to the left. The surrounding lawn is neatly mowed, and a deck is visible on the upper level with outdoor seating.
Guest suite in Howardsville
4.9 out of 5 average rating, 162 reviews

Whisper Creek Lodge! Lower Level Suite!

Whisper Creek! Located in the foothills of the Shenandoah Mountains. This Lower Level Suite will provide you and friends with the perfect place for back woods peace and quiet. Located one hour from UVA, Wintergreen, numerous Craft Beer Pubs and Wineries. This includes numerous choices for hiking. If canoeing and kayaking is your interest, I am located a short distance from several launch sites. I am willing to shuttle vehicles and assist in getting you where you wanna be.

Top guest favorite
Tiny home in Scottsville
4.99 out of 5 average rating, 497 reviews

Rare Find: Private Animal Sanctuary & Tiny Cottage

For animal lovers seeking an exclusive and unique getaway, this boutique Airbnb in Scottsville offers a tranquil escape where guests can unwind in nature and connect with the sanctuary’s resident animals. Recognized by Northern Virginia Magazine, Trips 101, and Trips to Discover as one of Virginia’s most distinctive stays, this thoughtfully curated retreat features cozy furnishings, charming handcrafted details, and an expansive window that showcases views of the animals.

Guest favorite
Home in Scottsville
4.91 out of 5 average rating, 211 reviews

1893 House on Wild Oats Farm

This traditional rambling farm house built in 1893 is located on a 130 acre working cattle farm in lovely rural Virginia. Enjoy your morning coffee with views of the pastures, pond and woods from 3 porches. The farm is conveniently located to Scottsville, Charlottesville, UVA, Monticello, Ashlawn Highland, the James River, Richmond, Mt. Ida and award winning winery's and breweries. 8 people max staying in house

Superhost
A cozy cabin with a striking red metal roof is set amidst lush greenery. A stone pathway leads to the entrance, framed by trees and ivy. A classic lantern stands nearby, complementing the rustic charm of the wooden structure.
Cabin in Appomattox
4.95 out of 5 average rating, 429 reviews

Cozy and Private Riverfront Cabin on 50 Acres

Voted “Coolest AirBnb in Virginia” by Condé Nast www.cntraveler.com/gallery/best-airbnbs-in-the-us Nestled amongst a stand of mature hardwood trees, atop a bluff overlooking the scenic Appomattox River, this cozy cabin is a great place to let your stress melt away. Originally built in the 1800's and moved to its current location in the 1970's, it offers old-school charm and modern comfort.

Top guest favorite
A spacious backyard features a well-manicured lawn surrounded by large trees and two distinct buildings. The gray house, featuring a porch, is complemented by a vibrant red structure, both capturing a serene outdoor setting.
Guesthouse in Cumberland
4.96 out of 5 average rating, 138 reviews

Lucid Dreams little house

Have fun at Lucid Dreams Little house on the farm. You can go dream walking and feel so free and peaceful. Open land and woods. A place you just don’t want to leave. Rocky the Mimi horse will greet you in the yard. Redneck beach in the back where picnics are always fun. Check out our beautiful sun rises and sunsets. Bring your horse or a friend.

Popular amenities for Dillwyn vacation rentals

  1. Airbnb
  2. United States
  3. Virginia
  4. Buckingham County
  5. Dillwyn