
Holiday houses in Pittsylvania County
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Pittsylvania County
Guests agree: these stays are highly rated for location, cleanliness and more.

Lovers retreat, walk to casino
Enjoy a trip away from your worries and strife by relaxing in this stylish couples haven that feels like stepping into your cottage Pinterest board. What better way to spend time away from home than in a spacious, artist-endowed retreat, far away from clutter, chores, and stress? Slip into a comfy bathrobe after a warm bath to watch tv, fall asleep listening to green noise, or enjoy coffee on the front porch. Ideal for longer stays- discounts applied. Extra linens and cleaning products supplied.

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.

Fun Lake Getaway with Breathtaking Views
Fantastic getaway on beautiful Smith Mountain Lake! Enjoy stunning views on two sides of this top-floor, corner condo with a wrap-around deck and natural shade. It is perfect for a relaxing break or an adventure! Activities include boating (with guest docks), swimming (indoor and outdoor), pickle ball, working out, and relaxing in the hot tub, steam room or sauna! If you are working remotely, this quiet space includes a desk and high-speed wireless. The individual HVAC unit also has a UV light.

Tranquility Cove Condo at Smith Mountain Lake
—We Welcome You— Visit and experience the ultimate respite while enjoying amazing water and mountain views, sunrises, and sunsets. This ground level condo is perfectly situated in Bernard's Landing Resort on beautiful Smith Mountain Lake! This bright, stylish & thoughtfully appointed space welcomes you to a full kitchen, spacious bdrm w/king bed, walk-in shower, and a queen sleep sofa. Amenities include restaurant & bar, tennis, pickle ball, gym, sauna, hot tub, three pools and a sandy beach.

Little Haven Cottage
Leave the demands of life and enter the peace of our Little Haven Cottage. Enter our rendition of an English cottage and enjoy watching local wildlife pass through the tranquility. Your stay will offer a repose and the ability to connect through a slow and quiet experience. Surrounded by the growing Amish community and stores where you can buy Amish food/goods. 45 min to Liberty University/ Lynchburg 40 min to Smith Mountain Lake Under 20 min to historic railroad towns Gretna/Chatham/Altavista

Antler Ridge Lodge
Only 3 miles from SMITH MOUNTAIN! Zip Code 24161. (There's another Sandy Level near NC.) It is well-stocked and waiting for your next get-a-way! Explore acres of yard, woods & creek. Leesville & SML beaches & boat launches are 9-30 miles away. Walk or ride 1/2-mi to the road's end at Leesville Lake. Horses/hikers/bikers are welcome along the 5-mi ridge of Smith Mt minutes away. Relax around a fire enjoying the starry sky or kick back in the comfortable lodge complete with a gas log fireplace.

Roark Mill Retreat
Welcome to the Roark Mill Retreat. Your cozy and private getaway located in the bottom level of our charming home on Roark Mill Road in Hurt, VA. This inviting space offers a comfortable queen bed along with a queen/twin bunk bed. We offer a well equipped kitchenette and a refreshing bathroom. Enjoy the convenience of a separate entrance and the tranquility of a peaceful neighborhood. Whether you’re here for one night or a longer stay, you’ll find everything you need for an enjoyable visit.

Dock Holiday at Bernard's Landing
Experience the water and mountain views at spectacular this 1 bedroom, 1 bath top floor corner condo in desirable Dockside section of Bernard's Landing. Guests enjoy all the amenities of Bernard's Landing including 2 outdoor and 1 indoor pool, Basketball, tennis and pickle ball courts,beach area, restaurant, fitness center and marina area with boat rentals. All pools and beach are short walk from the front door. Enjoy stunning views from the walk-out deck in this well-stocked condo.

Gorgeous Lakefront Cabin Resort: 5400sqft 6BR, 5ba
Welcome to the Lake Bear Lodge family! 5,400sqft private lakefront resort w a gorgeous view feat: * King bed suite * 6br, 5 bath * Massive Game Room! ~21 Arcades!!! ~75in TV ~Ping Pong ~2-player B-ball ~Pool Table ~Shuffleboard ~Bar w BT Speaker * Massive main living room w 70in TV * Private Dock * Firepit * Loaded Kitchen w Coffee Station * Huge Deck * 2 Screened Porch Areas (1 in master) * 6 kayaks, paddleboat * 2 paddleboards for rent, ask for price * Whirlpool bathtub * Gas grill

Comfy 3BR w/ large basement, deck, W/D, wifi
Our family's best memories occurred here - so we're opening our doors to groups looking to make memories of their own. With 3 bedrooms, 5 beds and free parking, there's room for everyone. Our huge family room with sleeper sectional, office nook, back deck, large yard, WiFi, large TVs, and games are reasons to stay in - but if you venture out, we're 10 minutes from the riverwalk and parks. With modern farmhouse decor, Retreat on Rosemary says, "Welcome to the South, y'all!"

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

Farmhouse in Gretna, Virginia

Little House at Leesville Lake

Cozy Danville Retreat

Peaceful Chatham Home w/ Grill & Deck

Hermione’s Purse

Cozy Cabin in the Country —NEWLY ADDED Fire Pit

Charming Lakefront Condo at Bernard's Landing

Hilltop Hideaway
Destinations to explore
- Rentals with pools Pittsylvania County
- Rentals with beach access Pittsylvania County
- House rentals Pittsylvania County
- Rentals with a patio Pittsylvania County
- Apartment rentals Pittsylvania County
- Rentals with lake access Pittsylvania County
- Family-friendly rentals Pittsylvania County
- Condo rentals Pittsylvania County
- Fitness-friendly rentals Pittsylvania County
- Rentals with a hot tub Pittsylvania County
- Rentals with a fire pit Pittsylvania County
- Pet-friendly rentals Pittsylvania County
- Waterfront rentals Pittsylvania County
- Beachfront rentals Pittsylvania County
- Rentals with a washing machine and dryer Pittsylvania County
- Rentals with a kayak Pittsylvania County
- Rentals with a fireplace Pittsylvania County
- Rentals with outdoor seating Pittsylvania County
- Smith Mountain Lake State Park
- Hanging Rock State Park
- Greensboro Science Center
- Amazement Square
- Ballyhack Golf Club
- National D-Day Memorial
- Liberty Mountain Snowflex Centre
- International Civil Rights Center & Museum
- Autumn Creek Vineyards
- Valhalla Vineyards
- Guilford Courthouse National Military Park
- Altillo Vineyards




