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

8 mi. to VIR! 18 min to Danville, South Boston, Va
Spacious, clean, & relaxing, this home is less than 8 miles from VIR and 18 mi to Danville, South Boston, or Roxboro. The listing is on one floor level to accommodate those with mobility issues. High-speed Starlink WiFi. Bedrooms provide linens/pillows/blankets. Bathrooms provide towels & necessities. Full kitchen w/coffee. Oversized paved parking with easy accessibility. Perfect for trailers/multiple large vehicles. Close to hwy, may want to pack earplugs. Strict no smoking or pets please.

Historic Gem w amenities * Midweek Stay Discounts*
Experience the best of Danville in this beautifully remodeled 1920’s gem! *MID-WEEK STAY DISCOUNT OF $30 OFF STAYS OF 3 NIGHTS OR MORE SUN-THUR* * 4 Bedrooms * 2 Full Bathrooms * 5 mins to Danville Caesars Virginia Casino * 20 mins to Virginia International Raceway * 35 mins to Martinsville Speedway * Fully Equipped Kitchen * Beautiful Deck with string lights/ yard games * Fire pit with Adirondack Chairs * Free Disney+ Streaming * Driveway & Street Parking * Walk to Averett or Downtown Danville

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.

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

Central Retreat with Gameroom Near 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.

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!"

Walking Distance to Casino
Step back in time without sacrificing comfort in this beautifully updated 2-bedroom mill house. Originally built in the early 1900s this charming home has been thoughtfully renovated to preserve its character while offering all the modern conveniences you expect. The Danville Caesars Virginia Casino is Just 0.5 mile distance and a short 9 minute walk. This home offers a private back deck with outdoor seating, fenced in backyard and a picnic table for additional seating.

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

Lakehouse on Leesville Lake in Bedford County VA
My late wife, Gail, & I came out of retirement to renovate this unique home with a completely new kitchen, vinyl plank flooring, new deck & new well in the Fall of 2019. This 3 bedroom lakehouse is very secluded within about an hour drive from Lynchburg, Roanoke or Danville. The dock and boat ramp are especially convenient. Keep an eye out for eagles, osprey, deer, bear, turkeys, otters, geese & heron.

Cute Comfy House
Only 1 mile from the new Caesars casino - Welcome to the cute comfy house! This home has 2 bedrooms with a queen in each room. There is an additional single person foldout cot in the closet. Freshly remodeled from top to bottom and situated on an acre in a quiet and peaceful neighborhood minutes away from Main St., Averette University, downtown and the Riverwalk. Washer/Dryer in the basement

Waterfront with Waterside, Diving Board & Arcade
Welcome to your 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!

Guest House near VIR, Hyco Lake, Dan River.
The guest home is surrounded by 6 acres of woods with trails leading to a scenic creek. Dan River canoeing & fishing can be accessed 1/2 mile away. VIR is only 7 miles away. Dan Daniels Memorial Park around 17 minutes drive and offers beautiful, scenic, paved walking & biking trails & fishing along Dan River with bike & canoe rentals. Hyco lake Marina is 9.5 miles away.
Popular amenities for house rentals in Pittsylvania County
House rentals with a pool

SML Retreat | Pool Table & Kayaks + Lake Amenities

Private Dock,Indoor Pool, and Hot Tub

Near VIR, Caesar's Casino, Firepit, Jacuzzi, Pool

Fairway Haven Golf Course/Lake Retreat

Casita Blanca White House dock the boat fish/swim

Smith Mountain Lake Retreat

Heron’s Cove on Leesville Lake.

4 BR Golf View House Mariners
Weekly house rentals

Farmhouse in Gretna, Virginia

The Grey Nest

Cozy Danville Retreat

Hycliff Lodge - water access

Private lakefront home - Kayaks, Dock, Quiet Cove

Martha - a view of 3 Sisters! Lucky Number 7!

Lakefront Gem Newly remodeled huge new dock

Lake Haven - Hot Tub! Mountain Views!
Private house rentals

Absolutely Shore

Kyle's Place

Serenity Cove - SML Lakefront

Waterfront Retreat: Kayaks, Dock & Family Fun!

Smith Mountain Lake / Blue Ridge

Relaxing oasis

Historic house w/modern touches

Lakefront Luxury: Hot Tub, Sleeps 12, Gentle Slope
Destinations to explore
- Rentals with beach access Pittsylvania County
- Rentals with a kayak Pittsylvania County
- Rentals with a fireplace Pittsylvania County
- Pet-friendly rentals Pittsylvania County
- Family-friendly rentals Pittsylvania County
- Rentals with a firepit Pittsylvania County
- Rentals with pools Pittsylvania County
- Rentals with a patio Pittsylvania County
- Waterfront rentals Pittsylvania County
- Rentals with lake access Pittsylvania County
- Rentals with outdoor seating Pittsylvania County
- Fitness-friendly rentals Pittsylvania County
- Rentals with a hot tub Pittsylvania County
- Flat rentals Pittsylvania County
- Rentals with a washing machine and dryer Pittsylvania County
- Apartment rentals Pittsylvania County
- Beachfront rentals Pittsylvania County
- House rentals Virginia
- House rentals United States
- 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
- Guilford Courthouse National Military Park
- Autumn Creek Vineyards
- Altillo Vineyards
- Valhalla Vineyards