Vacation rentals in Dillwyn

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Top-rated vacation rentals in Dillwyn

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Guest favorite

Home in Dillwyn

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.

4.9 out of 5 average rating, 185 reviews

Top guest favorite

Farm stay in Scottsville

Riverview at Belle Meade Farm

Sorry for the increase in pricing as Airbnb has rolled their guest fees into our daily rate instead of charging separately. Overall, total costs are the same as before this change. 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.

5.0 out of 5 average rating, 106 reviews

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

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.

5.0 out of 5 average rating, 152 reviews

Top guest favorite

A covered patio area features two reclining chairs, providing a comfortable space to relax. A charcoal grill is positioned under the awning, while potted plants add a touch of greenery. The backdrop showcases a lush woodland setting, enhancing the outdoor experience.

Guest suite in Howardsville

La-de-da studio near James River and Wineries

Welcome to La-de-da! We are located in beautiful, rural Howardsville, Virginia with convenient access to all the recreational amenities the James River has to offer. We are a VERY scenic 35 minutes to Wintergreen, all the wineries, breweries, distilleries and orchards in the region and great hiking trails! We are far enough outside of the cities of Charlottesville and Scottsville to provide peace and quiet, but just a scenic 20 minute drive to Scottsville and 40 minutes to Charlottesville.

4.91 out of 5 average rating, 171 reviews

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

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.

4.91 out of 5 average rating, 241 reviews

Top guest favorite

An aerial view captures the surrounding area, highlighting a baseball field with well-maintained grass and a nearby parking lot filled with cars. The landscape includes green trees and distant hills under a partly cloudy sky, showcasing the neighborhood's proximity to key facilities.

Home in Farmville

Farmville-Entire House - walk to Downtown & Campus

King Bed added. Entire house - you’ll be the only ones there. 3 Bedrooms & 2 Full Baths. It's like having 3 Hotel Rooms but you get a full kitchen & family room. Walk to Downtown Farmville / Longwood Univ. Primary BR has a King Bed / private bath w walk-in shower. BR 2 has a Queen bed & twin daybed w access to 2nd hall bath w tub. 3rd BR has a Queen bed w twin bunk. Great location across the street f/Longwood Baseball field. Your door code will be specific to you and not re used

4.99 out of 5 average rating, 163 reviews

Guest favorite

Home in Rice

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.

4.87 out of 5 average rating, 316 reviews

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

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.

4.9 out of 5 average rating, 170 reviews

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

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.

4.94 out of 5 average rating, 195 reviews

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

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.

4.99 out of 5 average rating, 522 reviews

Top guest favorite

A traditional two-story farmhouse with white siding is set against a lush green landscape. Two porches extend across the front, flanked by vibrant flower beds and well-maintained grass. The surrounding trees provide a natural backdrop, enhancing the serene rural atmosphere.

Home in Scottsville

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

4.91 out of 5 average rating, 225 reviews

Guest favorite

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

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.

4.95 out of 5 average rating, 444 reviews