Vacation rentals in Dillwyn

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Top-rated vacation rentals in Dillwyn

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Top guest favorite
A charming blue house is set on a green lot, framed by trees and bushes. The exterior features a welcoming front porch with steps leading up, and a gravel driveway accommodates multiple vehicles. Bright sunlight highlights the tidy, clean environment.
Bungalow in Scottsville
4.98 out of 5 average rating, 223 reviews

Scottsville Downtown Bungalow

Stay in downtown Scottsville. This little river town is very friendly. The house is neat and clean with central heat and air on a quiet side street. Have fun on the river tubing & kayaking. Walk to Van Clief Nature area, hiking trails, river, brewery & restaurants. It's about 20 miles from UVA and Yogaville & only a short drive to several wineries in the area. The covered front porch has a patio set for 4 to enjoy coffee or afternoon drinks. Due to allergies, I am unable to accommodate pets.

Top guest favorite
An aerial view captures a spacious rural landscape featuring a cozy guest house bordered by expansive green fields and trees. A pond is visible nearby, along with cultivated areas. The distant hills create a serene backdrop, emphasizing the tranquility of this working farm.
Guesthouse in Dillwyn
4.94 out of 5 average rating, 81 reviews

Cozy Farm Cottage near Farmville Virginia

Our cozy guest house is situated on a 36 acre working farm where you will enjoy privacy and pastoral views. Our posted rate is for 2 guests. The town of Farmville is an easy drive 10 miles south of us, where you will find Longwood University, Hampden-Sydney College, Green Front Furniture, the High Bridge Trail, and activities on the Appomattox River. Charlottesville, Richmond and Lynchburg are less than an hour away. Cottage has one bedroom with two twin beds, and one bedroom with a double bed.

Guest favorite
Home in Dillwyn
4.9 out of 5 average rating, 183 reviews

Lazy Bear Lodge | 12 Acre Fun Family Getaway

🐻 Welcome to The Lazy Bear Lodge 🐻—a one-of-a-kind 10 acre retreat where fun, fresh air, and unforgettable memories come naturally. Sleeping up to 12 guests, this spacious lodge features a wrap around deck, fully stocked kitchen, charming bear-themed décor, extremely clean accommodations, and incredible outdoor spaces with a huge fire pit, lawn games, hiking trails, and room to roam. It's the perfect escape for families and friends looking for a unique getaway that's as relaxing as it is fun.

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
4.99 out of 5 average rating, 141 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
5.0 out of 5 average rating, 151 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
Farm stay in Scottsville
5.0 out of 5 average rating, 105 reviews

Riverview at Belle Meade Farm

Escape to Belle Meade Farm, a magnificent 106-acre estate overlooking the James River, once owned by Thomas Jefferson's family. Nestled in the serene countryside, the property is just a mile away from historic downtown Scottsville, a short 25-minute drive to Charlottesville, and near many wineries and breweries. Experience the ultimate outdoor adventure by indulging in a plethora of activities, including petting the cats and dogs, catch and release fishing at our pond, or tubing the river!

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
4.91 out of 5 average rating, 240 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
Home in Rice
4.87 out of 5 average rating, 314 reviews

The Back House at Gully Tavern

Discover the perfect escape at our family-friendly cottage! Ideal for contractor crews, adventurers, or families seeking relaxation, our spot has it all. Nestled near trails, lakes, and wedding venues like The Barn @ Gully Tavern, enjoy hiking, fishing, or relaxing by the fire pit. Just 10 minutes from Longwood and 15 minutes from Twin Lakes State Park’s beach, it’s perfect for stargazing, grilling, and making memories. Escape to nature and experience convenience, relaxation, and fun.

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, 193 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, 168 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
A tiny house is set against a backdrop of colorful sunset skies. The exterior features blue siding with softly glowing lights around the entrance. Lawn chairs are positioned in front, inviting relaxation. Trees and greenery surround the area, enhancing the serene atmosphere.
Tiny home in Scottsville
4.99 out of 5 average rating, 520 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.

Top guest favorite
A two-story house constructed with natural materials is surrounded by mature trees and landscaped grounds. Large windows allow for ample natural light, and the brown wood deck wraps around the building, providing outdoor access from both floors. A clear path leads to the entrance.
Chalet in Dillwyn
5.0 out of 5 average rating, 72 reviews

Seven Springs, a cozy getaway sitting on 500 acres

The perfect place to get away from the hussle and bussle. ****No cleaning fees**** ****No Pets Allowed**** Seven Springs is a place for you to relax, be secluded, and enjoy rustic elegance at its best. The view offers fields and an appreciation of the beautiful standing timber. We call it Seven Springs because there are 7 natural springs that run together. One of the only Airbnb in the state of Virginia with it's own private 18 hole disc golf course!

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