
Holiday rentals in Pittsylvania County
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Top-rated holiday rentals in Pittsylvania County
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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.

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

Room to Roam
A haven for nature seekers, this home is just out of town with plenty of comfort that makes you feel a world away from stresses of life. Turn onto quiet back roads to our quaint little escape just along the edge of a timber farm where creeks and streams border this secluded property. There is plenty of land to roam as you explore and appreciate the wildlife. Absence of city lights makes the night sky a perfect backdrop for stargazing. Take time to get away from it all and enjoy some relaxation.

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!

Family Retreat w/Gameroom Near Averett and Casino
Enjoy the comfort and convenience of our spacious home, perfect for both short getaways and extended stays. It is only 5 minutes away from Caesars Casino and 30 minutes away from VIR. Our property is equipped with modern amenities you need for a comfortable and productive stay, including: * High-speed Wi-Fi * Dedicated workspace * Smart TVs in all bedrooms * Sound system (Bluetooth) in living rooms * Game room * BBQ grill Message me about weekly or extended stay discount.

Levi Hall Farmhouse- Whole House
This beautifully renovated farmhouse blends rustic charm with all the modern amenities needed for a relaxing and memorable stay. Nestled in a peaceful rural setting, the home features five spacious king bedrooms and four full bathrooms, thoughtfully designed for convenience and comfort. Fresh linens, plush towels, & toiletries are provided to make your stay as comfortable as possible. The kitchenette is minimal and tidy, meant for convenience rather than full-scale cooking.

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.

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.

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

18th Century Cabin Retreat
Come enjoy our 18th century cabin! They don't make them like this anymore. One side built in 1750, the other in 1825. Sit under the giant white oak and enjoy the country air. This is a wonderful retreat to kick back and relax. Enjoy the pool, horseshoes, and fire pit. In the winter months, cozy up by the wood stove or fire place with gas logs. NO PETS!!! Please do not bring your pets. Owners live on site, so if you are in need of anything, please ask!

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!

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.
Popular amenities for Pittsylvania County holiday rentals
Other great holiday rentals in Pittsylvania County

11-Acre Lakefront Escape w/ Two Cottages

Cozy cottage

Heart of Danville Renovated Modern 3bd/2ba.

"Remodeled Spacious Retreat"

Iconic Church Turned Unique Stay (Casino/VIR)

Beautiful Family Style Home

Hycliff Lodge - water access

Zen at Marker 10* Lakefront with Hot Tub!
Destinations to explore
- Pet-friendly rentals Pittsylvania County
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- Smith Mountain Lake State Park
- Hanging Rock State Park
- Greensboro Science Center
- Virginia International Raceway
- Fairy Stone State Park
- Guilford Courthouse National Military Park
- Liberty Mountain Snowflex Centre
- International Civil Rights Center & Museum
- National D-Day Memorial
- Martinsville Speedway
- Mill Mountain Zoo
- Percival's Island Natural Area
- Explore Park
- Taubman Museum of Art
- Mill Mountain Star
- Elon University
- Tanger Family Bicentennial Garden
- Virginia Museum of Transportation
- Harvester Performance Center
- SeaQuest Lynchburg
- Greensboro Country Club
- Amazement Square





