
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.

Cute and Comfy Cabin, Stunning Lakefront Views,
Every season offers something special be it summer on the water, fall foliage, cozy winters by the electric fireplace, and blooming springs. Book your stay & experience why guests return year after year. Wake up to panoramic lake and mountain views in a peaceful, no-wake 60 acre cove, perfect for fishing, relaxing, reconnecting, and making memories. Inside, this cabin you’ll find a playful bear-themed décor that guests of all ages love—adding a fun, memorable touch to your stay. See Notes

The Historic Blessing House in Danville on Main
Located on historic Main Street, the home has central HVAC, is workspace friendly, w/ tv and walking distance to coffee shop/wine bar/restaurant/museum/ hospital. Averette Univ is 6 blocks. Casino 1 mi Queen bed, ceiling fan, window blinds, drapes, full floor mirror & walk-in closet. Full kitchen w/ ceiling fan, coffee, tea, Keurig, bottled water, disinfectant, sanitizer, and cooking essentials. Private Bath with shower, soap, shampoo, conditioner, hair dryer. Linens incl. W/D available.

Lake Lover's Paradise
Come to the lake! This spacious one bedroom top floor end unit is uniquely located between Napoli by the Lake restaurant and large outdoor swimming pool. Fantastic views of the lake from the large deck! Sleeps 2 adults and 2 small children under three. The following amenities are provided during your stay (Subject to season and repair): 2 Outdoor Pools Exercise Room Boat & Jet Ski Rental 1 Indoor Pool Hot Tub Courtesy Boat Slips Beach & Boat Launch Area Tennis & Pickleball Courts

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.

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.

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!

Heart of Danville Renovated Modern 3bd/2ba.
Newly renovated ranch in the heart of Danville. As you enter the front door is a sitting room to relax and enjoy reading a good book. Three bedrooms with King Size Beds and 60” Smart TVs . Enter the open floor plan from the kitchen into family room with the fireplace, 65” Smart TV, a new modern style sectional sofa and chair for a relaxing stay. Outdoor eating on the new deck. A Fire Pit is located in the backyard for sitting around a cozy fire.

The Empty Nest
Located just 2.7 miles from Caesars Virginia and 2 miles from the NC state line, the Empty Nest is your perfect getaway. With Virginia International Raceway 20 miles away and Martinsville Speedway just 30 miles, it's an ideal base for both adventure and relaxation. Enjoy the comfort and convenience of this charming retreat!

Relaxing 1bd/1bth Apt | 1.8 miles from Casino
This NEWLY furnished, top floor apartment space is located on Main Street in the heart of the Old West End. Enjoy being walking distance to two local restaurants: Crema & Vine as well as Kingg Crop while being just a few minutes drive from the Casino and other attractions. Your positive experience is our top priority!
Popular amenities for Pittsylvania County holiday rentals
Other great holiday rentals in Pittsylvania County

Little House at Leesville Lake

Roark Mill Retreat

Cozy cottage

The Cedar Farm | Close To VIR, Danville

La Buena Vida Retreat

"Remodeled Spacious Retreat"

11-Acre Lakefront Escape w/ Two Cottages

Relax & Recharge at This Charming Country Home
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
- Elon University
- Guilford Courthouse National Military Park
- Liberty Mountain Snowflex Centre
- International Civil Rights Center & Museum
- National D-Day Memorial
- Amazement Square
- Martinsville Speedway
- Mill Mountain Zoo
- Percival's Island Natural Area
- Explore Park
- Taubman Museum of Art
- Mill Mountain Star
- Tanger Family Bicentennial Garden
- Virginia Museum of Transportation
- Harvester Performance Center
- SeaQuest Lynchburg
- Greensboro Country Club





