Pittsville holiday homes

We found 554 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Pittsville to find one that's perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include cable TV and a washer and dryer. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Pittsville

Showing deals for:6 Nov - 13 Nov

Great Room
View from house
King Bedroom 2 with lake view
Shoreline walkway
Exceptional
(11 reviews)

Blue Heron Cottage, Dock, Beach, Peaceful Cove, SUPs, Canoe, Kayaks, Ping Pong

Huddleston

7% off
NZ$6,937
for 7 nights, 1 home
NZ$991 per night
includes taxes & fees
Blue Heron Cottage, Dock, Beach, Peaceful Cove, SUPs, Canoe, Kayaks, Ping Pong
Lake Path
Cabin
Kitchen Bar
Dining
Exceptional
(321 reviews)

Unique Historical log cabin with private beach and 300 ft. of waterfrontage.

Huddleston

7% off
NZ$2,219
for 7 nights, 1 cabin
NZ$317 per night
includes taxes & fees
Unique Historical log cabin with private beach and 300 ft. of waterfrontage.
Aerial View from Driveway
Great Room Looking Down from Balcony with Glass Railing
Heron Point
Open Plan Kitchen/Dining/Great Room Areas from Entry
Exceptional
(210 reviews)

Heron Point - Amazing Property with Breathtaking Water Views - Luxury Hot Tub!

Huddleston

13% off
NZ$14,621
for 7 nights, 1 home
NZ$2,089 per night
includes taxes & fees
Heron Point - Amazing Property with Breathtaking Water Views - Luxury Hot Tub!
Dock and Fire-pit
View from upstairs porch
Screened porches, great for AM coffee
granite counters in kitchen
Exceptional
(88 reviews)

Mountain View, waterfront, large quiet cove, gentle lot, covered dock & deep H2O

Huddleston

8% off
NZ$5,136
for 7 nights, 1 home
NZ$734 per night
includes taxes & fees
Mountain View, waterfront, large quiet cove, gentle lot, covered dock & deep H2O
Living area
Outdoor dining
Exterior
Interior
Exceptional
(26 reviews)

The Grandview Lodge, Oasis at Smith Mountain Lake!

Huddleston

8% off
NZ$9,222
for 7 nights, 1 home
NZ$1,317 per night
includes taxes & fees
The Grandview Lodge, Oasis at Smith Mountain Lake!
New Playground equipment right by the clubhouse pool.
Conference Center pool with great views of the mountains
Porch with covered ceiling and fan (grill now sits on ground and no paddleboard)
Back of our building. We are in the middle closest to the courtesy boat slips.
Exceptional
(152 reviews)

PENINSULA PARADISE at BERNARD'S LANDING! Closest to the Water!!!

Moneta

8% off
NZ$2,679
for 7 nights, 1 apartment
NZ$383 per night
includes taxes & fees
PENINSULA PARADISE at BERNARD'S LANDING! Closest to the Water!!!
Dining
Living area
Private kitchen
Outdoor spa tub
Exceptional
(18 reviews)

Romantic Luxury Lake Access Cabin w/ Hot Tub, Spacious Deck, and Pine walls

Pittsville

8% off
NZ$2,581
for 7 nights, 1 cabin
NZ$369 per night
includes taxes & fees
Romantic Luxury Lake Access Cabin w/ Hot Tub, Spacious Deck, and Pine walls
Property grounds
Property grounds
Kitchen
Living area
Exceptional
(47 reviews)

Bright, Beautiful Smith Mountain Lakefront, Full Amenities & Perfect Location!

Moneta

7% off
NZ$7,892
for 7 nights, 1 home
NZ$1,127 per night
includes taxes & fees
Bright, Beautiful Smith Mountain Lakefront, Full Amenities & Perfect Location!
Outdoor dining
Exterior
Private kitchen
Private kitchen
Exceptional
(80 reviews)

Spacious 2BR + Loft Condo • Pool • Gorgeous Lake View

Huddleston

8% off
NZ$2,679
for 7 nights, 1 apartment
NZ$383 per night
includes taxes & fees
Spacious 2BR + Loft Condo • Pool • Gorgeous Lake View
Beach at the pointe
Pointe
Pointe
Screen porch
Exceptional
(43 reviews)

CATCHING RAEs on Quiet Cove

Huddleston

7% off
NZ$3,602
for 7 nights, 1 apartment
NZ$515 per night
includes taxes & fees
CATCHING RAEs on Quiet Cove
Living Room Upstairs
Lounge chairs
House View
View from Deck
Exceptional
(58 reviews)

Deep Water / Mountain View Waterfront / 3 King Beds / Kayaks, SUP

Huddleston

7% off
NZ$13,004
for 7 nights, 1 home
NZ$1,858 per night
includes taxes & fees
Deep Water / Mountain View Waterfront / 3 King Beds / Kayaks, SUP
Property grounds
Living area
Dining
Exterior
Exceptional
(5 reviews)

Sunset Lake House with private dock and game room

Penhook

8% off
NZ$11,698
for 7 nights, 1 home
NZ$1,671 per night
includes taxes & fees
Sunset Lake House with private dock and game room
Master Bedroom
Exterior
Private kitchen
Exterior
Exceptional
(115 reviews)

Smith Mtn Lake 3 BR, 3 bath Lakefront Home; private with great location

Moneta

8% off
NZ$3,293
for 7 nights, 1 home
NZ$470 per night
includes taxes & fees
Smith Mtn Lake 3 BR, 3 bath Lakefront Home; private with great location
Parking Entrance to the condo
Sunset from the living room
Aerial View of The Clubhouse with large outdoor pool, tennis/pickleball courts
Indoor Hot Tub is open year round!
Exceptional
(108 reviews)

Amazing Views and Two Kayaks Ready to Use!

Moneta

7% off
NZ$2,806
for 7 nights, 1 apartment
NZ$401 per night
includes taxes & fees
Amazing Views and Two Kayaks Ready to Use!
Kitchen
Living Room
Lakefront Pool at the Pointe
Mariners Cottage Lake Retreat
Exceptional
(12 reviews)

Mariners Cottage - Stunning SML Getaway with Resort Perks at Mariners Landing!

Huddleston

8% off
NZ$5,760
for 7 nights, 1 home
NZ$823 per night
includes taxes & fees
Mariners Cottage - Stunning SML Getaway with Resort Perks at Mariners Landing!
Indoor pool at the Bernard’s Landing Clubhouse - Hot tub is around the corner.
Outdoor dining
Living area
Interior
Exceptional
(68 reviews)

Charming Lakefront Condo at Bernard's Landing, only steps from the shore!

Moneta

8% off
NZ$3,275
for 7 nights, 1 apartment
NZ$468 per night
includes taxes & fees
Charming Lakefront Condo at Bernard's Landing, only steps from the shore!
Pool
Exterior
View from balcony
Beach
Exceptional
(122 reviews)

Condo with great Lake views. Come stay with us on your vacation 

Huddleston

7% off
NZ$4,699
for 7 nights, 1 apartment
NZ$671 per night
includes taxes & fees
Condo with great Lake views. Come stay with us on your vacation 
Private kitchen
Outdoor spa tub
Room
Living area
Very good
(10 reviews)

Charming 2-bedroom Cottage located at Va Dare and Portside Bar! Sleeps 4

Moneta

7% off
NZ$2,238
for 7 nights, 1 apartment
NZ$320 per night
includes taxes & fees
Charming 2-bedroom Cottage located at Va Dare and Portside Bar! Sleeps 4
The Pointe at Mariners Landing.
Sunset at The Pointe pool.
The Landing Restaurant.
ariel shot of The Pointe.
Wonderful
(15 reviews)

Mariners Landing Condo at SML. AMENITY OVERLOAD!

Huddleston

7% off
NZ$2,480
for 7 nights, 1 apartment
NZ$354 per night
includes taxes & fees
Mariners Landing Condo at SML. AMENITY OVERLOAD!
New awning for deck enjoyment.
Beautiful pool & lake view!
Stripers Landing from the water
View of condos & walkway from  boat slip-Drive down for easier access
Pool
Exceptional
(167 reviews)

SUNSET VIEWS-Pristine WATERFRONT Penthouse Condo on SML- Boat Slip Available

Moneta

8% off
NZ$1,785
for 7 nights, 1 apartment
NZ$255 per night
includes taxes & fees
SUNSET VIEWS-Pristine WATERFRONT Penthouse Condo on SML- Boat Slip Available
Property grounds
Beach
Living area
Room
Exceptional
(25 reviews)

Two-Level Penthouse with stunning views of Smith Mountain Lake. 3 bed. 3.5 bath

Huddleston

8% off
NZ$5,962
for 7 nights, 1 apartment
NZ$852 per night
includes taxes & fees
Two-Level Penthouse with stunning views of Smith Mountain Lake. 3 bed. 3.5 bath
Room
Property grounds
Private kitchen
Interior
Exceptional
(25 reviews)

Waterfront Townhome- with Boat Slip and Dock!

Moneta

8% off
NZ$3,557
for 7 nights, 1 home
NZ$508 per night
includes taxes & fees
Waterfront Townhome- with Boat Slip and Dock!
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Pittsville getaway

Learn about the unique charm of Pittsville with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Pittsville

Do you want to discover attractions to see in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Pittsville a fun spot to go on holiday. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Hickory Hill Vineyards (13.8 mi / 22.3 km)
  • Tomahawk Mill Vineyard and Winery (8.1 mi / 13 km)

Exploring the natural features in Pittsville

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Pittsville is a great spot to appreciate mother nature. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Smith Mountain Lake (10.9 mi / 17.5 km)
  • Leesville Lake (7.5 mi / 12.1 km)
  • Smith Mountain Lake State Park (10.2 mi / 16.5 km)
  • Smith Mountain Lake Community Park (11.3 mi / 18.2 km)
  • Shreve Park (13.2 mi / 21.2 km)
  • Leonard Coleman Memorial Park (13.4 mi / 21.5 km)

How to get to and around Pittsville

The nearest airport is in Lynchburg, VA (LYH-Lynchburg Regional), located 28.3 mi (45.5 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Danville, VA (DAN-Danville Regional), which is 28.9 mi (46.5 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Pittsville?
The average price for a holiday home in Pittsville can vary depending on factors like season, property type and length of stay. Whether you're dreaming about a sprawling villa with a pool or a cosy condo just for the two of you, just enter your travel dates to view stays with fantastic value.
How much does it cost to rent a beach house in Pittsville?
The average price for a holiday home by the beach in Pittsville depends on when you're going and the size and type of property you want. You can easily and quickly find prices on Bookabach by entering your destination and travel dates. Then use our filter tool to choose the number of bedrooms and amenities that you prefer, like air conditioning, WiFi and a pool.
How old do you have to be to rent a holiday home in Pittsville?
The minimum age requirements can differ across properties on Bookabach, so double-check the rules of the holiday home in Pittsville you're interested in. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Pittsville for?
How long you can rent a holiday home in Pittsville varies according to the property. Just enter your desired travel dates to display a list of options offering extended stays. With a range of amenities like air conditioning and kitchens, as well as some offering discounted weekly or monthly prices, you're sure to find someplace just right to call your home away from home in Pittsville.