Vacation rentals in Pittsylvania County

4.97 out of 5 average rating, 262 reviews

A charming lodge exterior is framed by a large tree, showcasing a cozy structure with a sloped roof and a brick chimney. Outdoor seating is arranged near a gravel area, inviting relaxation in a serene natural setting.

Home in Sandy Level

Antler Ridge Lodge - 19 Acres of Seclusion +WiFi

Only 12-mi to the Anthony Ford Boat Launch at SML, 8-mi to Myers Creek ramp at Leesville Lake. Well-stocked and waiting for your next get-a-way! Explore acres of yard, woods & creek. Leesville Lake only a 1/2-mi walk to the end of the road. Horses/hikers/bikers are welcome along the 5-mi ridge of Smith Mt only 3-mi away. Relax around a fire enjoying the starry sky or kick back in the comfortable lodge complete with a gas log fireplace, 65" Smart TV, & Fiber WiFi, 50 MBS up & down. Pet friendly.

A welcoming entryway features an archway leading to a cozy living area, illuminated softly from a nearby lamp. Framed botanical art adorns the walls, alongside decorative plants in stylish pots. A neutral rug adds warmth and texture to the wooden floor.

5.0 out of 5 average rating, 106 reviews

BRAND NEW! Charming 2 Br home...great location!!!

Perfectly nestled in a quiet, safe neighborhood! Centrally located near the downtown River District and Riverwalk Trail, Averett Univ., SOVAH Health and great restaurants. Professionally renovated, decorated and landscaped with attention to details to make your stay comfortable and enjoyable! Screened porch for coffee and birdwatching, fresh herbs and flowers for cutting, great internet for home office and smart tvs in every room. Well supplied throughout to make the perfect home away from home

4.95 out of 5 average rating, 213 reviews

A lakehouse is framed against a vibrant sunrise, with soft hues of orange and pink reflecting on the tranquil water. The structure features a wraparound deck, and a slight mist hovers above the lake, enhancing the serene atmosphere of the secluded setting.

Home in Pittsville

Lakehouse on Leesville Lake in Bedford County VA

This secluded, 3 bedroom lakefront home was renovated In 2019. My late wife Gail and I installed a new kitchen, vinyl plank flooring, new well, and new decks (both wraparound and lower deck.) The home is located about an hours drive from Lynchburg, Roanoke or Danville. Enjoy our private dock and boat ramp for fishing, watercraft, swimming, and nature watching! Keep an eye out for wildlife, both great and small! Great Blue Herons, Eagles and Osprey are personal favorites!

4.91 out of 5 average rating, 117 reviews

A modernized cabin is set in a serene natural environment, surrounded by green grass and trees. A covered porch is featured at the front, with rocking chairs and a porch swing positioned for relaxation. A pathway leads to the cabin, enhancing accessibility.

Cabin in Long Island

100acre Woods Cabin Retreat

No Smoking in home, No animals or pets allowed! 30 mi to Lynchburg, 11 to Altavista. This cabin boasts 100 acres of serene nature while hiking the trails, and with just a 20 minute hike you can be at the boat slip, fishing, and swimming in the river . Relax on the large rocking chair front porch with your honey on the porch swing, or roast marshmallows and sip drinks around the fire pit! This is not a party house, it is meant to relax and enjoy peace, quiet, and nature, enjoy!

4.91 out of 5 average rating, 34 reviews

Cozy cottage

Stay at this beautifully renovated, 1940s cottage, right on the outskirts of Danville. Perfectly placed on a calm street, you will be able to relax while only being 5-10 minutes from all stores and attractions. The space is cute and cozy with everything you need to feel right at home! **PLEASE READ** This home was built in the 1940s. The ceilings are low. Most rooms are around 7 ft. The living room is 6’ 8”. If you are a taller person, the ceiling height may be uncomfortable.

5.0 out of 5 average rating, 41 reviews

Home in Chatham

Hermione’s Purse

In the heart of downtown Chatham just across the creek from Chatham Hall, you will find a tiny home with room for everyone. Private and quiet with sweeping green views, Hermione’s Purse is within easy walking distance of both private schools and all downtown businesses. Built to last in 1960, the original part of the home consists of the living room and kitchen, with two bedrooms upstairs. The home’s first indoor bathroom and a bedroom downstairs were added in the 1980s.

4.97 out of 5 average rating, 38 reviews

Home in Huddleston

Cozy SML Lakeside Cottage with Dock & Kayaks

Escape to this cozy lakeside cottage—perfect for couples or small families. Enjoy stunning views, direct lake access, and peaceful vibes. Lounge on the private dock or deck, swim, fish, or paddle out with two included kayaks or an inflatable paddleboard. A gentle sloping lawn leads to the water, plus a boat ramp (9'8" wide) and a private dock make lake adventures easy. Whether sipping coffee at sunrise or exploring the lake, this retreat blends comfort with outdoor charm.

The exterior of a historic house features a covered front porch and a rooftop veranda with seating. Lush greenery surrounds the property, and a well-maintained lawn offers a welcoming appearance. The structure showcases a blend of classic design with modern renovation elements.

4.96 out of 5 average rating, 103 reviews

Historic house w/modern touches

*20% WEEKDAY DISCOUNTS* Centrally located near historic downtown, Averett U, and Caesar’s, this 100-yr-old beauty has been attractively renovated & tastefully appointed with curated furnishings to modernize it while maintaining its historic roots. Covered front porch and rooftop veranda for savoring a lazy morning or unwinding at day’s end. Spacious main level en-suite Master bedroom; stunning, fully equipped kitchen; office space; bunkbeds and game room for the kids.

4.98 out of 5 average rating, 93 reviews

The exterior of a charming single-story home features white siding, a grey roof, and two front entrances. A well-maintained lawn with green grass surrounds the house, and trees with autumn foliage provide a colorful backdrop. A paved walkway leads to the front doors.

Home in Gretna

Nellie’s Nest

This adorable three bedroom is perfect for your stay in Gretna. Hit the sidewalks for a run or walk down to the best coffee shop around, The Pod. Take a quick 15 min drive to Smith Mountain Lake or visit the wineries just outside of town. Relaxed living at it's best here in small town Virginia! *More photos coming Common Destinations: Chatham Hall and Hargrave Military Academy - 12 mins Olde Dominion Agricultural Complex - 6 mins Liberty University - 36 miles

4.96 out of 5 average rating, 188 reviews

Home in Huddleston

Diving Board, Waterslide, Private, Lakefront

Welcome to this peaceful & private 1-acre A-Frame lakefront escape on stunning Smith Mountain Lake, VA! Enjoy sweeping wide-water views, breathtaking sunsets, and mountain vistas from four serene outdoor living spaces. Jump in the crystal clear lake from the dock’s diving board, race down the waterslide, or just relax in total privacy. Peaceful, fun, and unforgettable, this is lake life at its best!

4.93 out of 5 average rating, 175 reviews

Farm stay in Union Hall

Pine Haven Farms

Make memories at this unique and family-friendly place. Pine Haven Farms is a working farm. Spread out and enjoy the pastoral surroundings. We are located less than two miles away from Magnum Point Marina at Smith Mountain Lake if you want to add some lake time to your vacation stay. Please be aware that electric fencing is used for the cattle. Children should be supervised at all times.

Superhost

The living room features a comfortable black leather sofa and a classic armchair with a patterned design. A coffee table sits centrally on a patterned area rug, while a TV is mounted on the wall. Natural light enters through the windows, enhancing the space.