Book Holiday Homes in Pittsville

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Pittsville

Private pool and hot tub, paddleboard, ping pong

Private pool and hot tub, paddleboard, ping pong

Goodview
When you stay at this vacation home in Goodview, you'll be on the waterfront and 6 minutes by car from Smith Mountain Lake.
Private pool and hot tub, paddleboard, ping pong
Hot tub, Dock, Fire Pit, Dog Friendly, Golf,

Hot tub, Dock, Fire Pit, Dog Friendly, Golf,

Huddleston
With a stay at this vacation home in Huddleston, you'll be on the waterfront, just steps from Smith Mountain Lake.
Hot tub, Dock, Fire Pit, Dog Friendly, Golf,
Charming SML lake front 3-bedroom house with WiFi and AC in beautiful Huddleston

Charming SML lake front 3-bedroom house with WiFi and AC in beautiful Huddleston

Huddleston
With a stay at this vacation home in Huddleston, you'll be on the waterfront and 3 minutes by foot from Smith Mountain Lake.
Charming SML lake front 3-bedroom house with WiFi and AC in beautiful Huddleston
Save an average of 15% on thousands of hotels when you're signed in
Splendid dog friendly home with shared pool, kayaks & free WIFI

Splendid dog friendly home with shared pool, kayaks & free WIFI

2 out of 5
Goodview
With a stay at this vacation home in Goodview, you'll be on the waterfront, within a 15-minute drive of Smith Mountain Lake and Moneta Library.
Splendid dog friendly home with shared pool, kayaks & free WIFI
Spacious dog-friendly house w/fire pit, deck, patio & grill

Spacious dog-friendly house w/fire pit, deck, patio & grill

Huddleston
When you stay at this vacation home in Huddleston, you'll be on the waterfront, a 1-minute drive from Smith Mountain Lake and 8 minutes from Smith Mountain Lake ...
Spacious dog-friendly house w/fire pit, deck, patio & grill
Lakefront home with views, private hot tub/dock, deck, Free Wifi

Lakefront home with views, private hot tub/dock, deck, Free Wifi

2 out of 5
Moneta
With a stay at this vacation home in Moneta, you'll be on the waterfront, within a 10-minute drive of Smith Mountain Lake and Crystal Shores Marina.
Lakefront home with views, private hot tub/dock, deck, Free Wifi
Shangri-La -dogs friendly, firepit, wifi, 2 kayaks, 2 kitchens, and a Pool Table

Shangri-La -dogs friendly, firepit, wifi, 2 kayaks, 2 kitchens, and a Pool Table

Huddleston
When you stay at this vacation home in Huddleston, you'll be 5 minutes by foot from Smith Mountain Lake.
Shangri-La -dogs friendly, firepit, wifi, 2 kayaks, 2 kitchens, and a Pool Table
Private house on Leesville Lake

Private house on Leesville Lake

Pittsville
When you stay at this vacation home in Pittsville, you'll be on a lake and within a 5-minute drive of Leesville Lake.
Private house on Leesville Lake
Sandy Bottom Cove, New Lakefront Luxury w/ Covered Decks + Heated Salt Pool, Beach, Hot Tub, Dock!

Sandy Bottom Cove, New Lakefront Luxury w/ Covered Decks + Heated Salt Pool, Beach, Hot Tub, Dock!

Moneta
With a stay at this vacation home in Moneta, you'll be on the waterfront, within a 15-minute drive of Smith Mountain Lake and Hickory Hill Vineyards.
Sandy Bottom Cove, New Lakefront Luxury w/ Covered Decks + Heated Salt Pool, Beach, Hot Tub, Dock!
Don't see what you're looking for?
See all available properties in Pittsville
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Pittsville Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Pittsville vacation homes are the perfect way for you to wing it.

Holiday houses in Pittsville let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Pittsville in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Pittsville adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Pittsville with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Pittsville vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Pittsville Holiday Homes essential information

Accommodation
442 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Private pool and hot tub, paddleboard, ping pong, Hot tub, Dock, Fire Pit, Dog Friendly, Golf, , Charming SML lake front 3-bedroom house with WiFi and AC in beautiful Huddleston, Splendid dog friendly home with shared pool, kayaks & free WIFI, Spacious dog-friendly house w/fire pit, deck, patio & grill, Lakefront home with views, private hot tub/dock, deck, Free Wifi, Shangri-La -dogs friendly, firepit, wifi, 2 kayaks, 2 kitchens, and a Pool Table, Private house on Leesville Lake, Sandy Bottom Cove, New Lakefront Luxury w/ Covered Decks + Heated Salt Pool, Beach, Hot Tub, Dock!

Top trending hotels in Pittsville

Private house on Leesville Lake

Private house on Leesville Lake

Pittsville
When you stay at this vacation home in Pittsville, you'll be on a lake and within a 5-minute drive of Leesville Lake.
Private house on Leesville Lake
Stylish Creekside Cabin w/ Fire Pit Near Wineries

Stylish Creekside Cabin w/ Fire Pit Near Wineries

Pittsville
With a stay at this cabin in Staunton River, you'll be in the mountains, and 18.9 mi (30.4 km) from Smith Mountain Lake and 23.8 mi (38.3 km) from Smith Mountain ...
Stylish Creekside Cabin w/ Fire Pit Near Wineries
Lakeinn

Lakeinn

2.5 out of 5
45 Enterprise Ln, Moneta, VA
Fully refundableReserve now, pay when you stay
With a stay at Lakeinn in Moneta, you'll be near the beach, within a 10-minute drive of Smith Mountain Lake and Booker T. Washington National Monument.
Lakeinn
Save an average of 15% on thousands of hotels when you're signed in
Days Inn by Wyndham Altavista

Days Inn by Wyndham Altavista

2.5 out of 5
1557 Main St, Altavista, VA
Fully refundableReserve now, pay when you stay
Located in Altavista, Days Inn by Wyndham Altavista is within a 5-minute drive of Avoca Museum and Town & Country Shopping Center.
Days Inn by Wyndham Altavista
Don't see what you're looking for?
See all available properties in Pittsville
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.