Pittsville Holiday Rentals

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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Pittsville holiday rentals

Outdoor dining
Private 2 Bedroom Suite at Boutique Inn with Hot Tub

Private 2 Bedroom Suite at Boutique Inn with Hot Tub

Private 2 Bedroom Suite at Boutique Inn with Hot Tub
2.0 star property
Altavista
The price is HK$944
HK$2,114 total
includes taxes & fees
4 Jan - 5 Jan 2026
Private 2 Bedroom Suite at Boutique Inn with Hot Tub
Interior
Restored 1840's Downtown Loft Near Blue Ridge Parkway

Restored 1840's Downtown Loft Near Blue Ridge Parkway

Restored 1840's Downtown Loft Near Blue Ridge Parkway
Historic Centertown Bedford
10.0 out of 10, Exceptional, (257)
"Great stay"
United States
John
The price is HK$699
HK$1,329 total
includes taxes & fees
1 Jan - 2 Jan 2026
Restored 1840's Downtown Loft Near Blue Ridge Parkway
Exterior
Cedar’s Rest Cabin

Cedar’s Rest Cabin

Cedar’s Rest Cabin
Bedford
10.0 out of 10, Exceptional, (82)
"This was our second stay and will be going for the third!"
United States
Donna B.
The price is HK$1,322
HK$2,200 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cedar’s Rest Cabin
Interior
Modern Altavista Farmhouse w/ Countryside Views

Modern Altavista Farmhouse w/ Countryside Views

Modern Altavista Farmhouse w/ Countryside Views
3.0 star property
Altavista
6.0 out of 10, (2)
"We booked the beautiful house to stay in for our daughter’s freshman move-in at Liberty University. She actually said that this was the best place I’ve ever booked (for anything). IT IS BEAUTIFUL, inside and out. The house was exceptionally clean and even had a nice subtle fresh scent. There were snacks, which were a hit with our 3 college-aged young adults. I feel that the hosts put their heart into every detail of our stay. We truly appreciated the hospitality of our hosts, and the memories...
United States
Rachel
The price is HK$1,143
HK$2,986 total
includes taxes & fees
31 Dec - 1 Jan 2026
Modern Altavista Farmhouse w/ Countryside Views
Terrace/patio
Boat, fish, golf, swim, & dine at Mariners Landing on Smith Mountain Lake!

Boat, fish, golf, swim, & dine at Mariners Landing on Smith Mountain Lake!

Boat, fish, golf, swim, & dine at Mariners Landing on Smith Mountain Lake!
Huddleston
10.0 out of 10, Exceptional, (27)
"Excellent stay. Host was very accommodating on a last minute weekend getaway booking. Love this location on SML."
United States
Amy C.
The price is HK$692
HK$1,981 total
includes taxes & fees
2 Jan - 3 Jan 2026
Boat, fish, golf, swim, & dine at Mariners Landing on Smith Mountain Lake!
Property grounds
MV37 Corner Waterfront Mariners: 2 Bedroom

MV37 Corner Waterfront Mariners: 2 Bedroom

MV37 Corner Waterfront Mariners: 2 Bedroom
3.0 star property
Bedford County
10.0 out of 10, Exceptional, (4)
"I would stay here again. "
United States
Zarela J.
The price is HK$1,704
HK$3,849 total
includes taxes & fees
1 Jan - 2 Jan 2026
MV37 Corner Waterfront Mariners: 2 Bedroom
Smart TV, stereo
Charming newly remodeled 1890’s, 3bd, 1Ba Downtown Bedford Loft

Charming newly remodeled 1890’s, 3bd, 1Ba Downtown Bedford Loft

Charming newly remodeled 1890’s, 3bd, 1Ba Downtown Bedford Loft
Historic Centertown Bedford
10.0 out of 10, Exceptional, (35)
"We very much enjoyed our stay. Everything about the loft was great, very clean and comfortable. We look forward to staying again."
United States
Terri T.
The price is HK$909
HK$1,629 total
includes taxes & fees
31 Dec - 1 Jan 2026
Charming newly remodeled 1890’s, 3bd, 1Ba Downtown Bedford Loft
Pool
Heron’s Cove on Leesville Lake.

Heron’s Cove on Leesville Lake.

Heron’s Cove on Leesville Lake.
Gretna
8.4 out of 10, Very good, (14)
"It was beautiful "
United States
Jenny W.
The price is HK$1,315
HK$2,599 total
includes taxes & fees
31 Dec - 1 Jan 2026
Heron’s Cove on Leesville Lake.
Pool
Cosy Lakefront Condo -- 1-bedroom w/WiFi & fitness room in wonderful Huddleston

Cosy Lakefront Condo -- 1-bedroom w/WiFi & fitness room in wonderful Huddleston

Cosy Lakefront Condo -- 1-bedroom w/WiFi & fitness room in wonderful Huddleston
Huddleston
8.2 out of 10, Very good, (14)
"What a great location. Beautiful lake views and boats available to rent within walking distance. The check-in process was very easy and the property had everything we needed."
United States
Beth Kimmick, Realtor, E.
The price is HK$381
HK$777 total
includes taxes & fees
11 Jan - 12 Jan 2026
Cosy Lakefront Condo -- 1-bedroom w/WiFi & fitness room in wonderful Huddleston
Exterior
Beautiful condo lakefront beautiful views, relaxing times what else do you need?

Beautiful condo lakefront beautiful views, relaxing times what else do you need?

Beautiful condo lakefront beautiful views, relaxing times what else do you need?
Huddleston
10.0 out of 10, Exceptional, (103)
"Beautiful place. Condo excellent."
United States
James B.
Beautiful condo lakefront beautiful views, relaxing times what else do you need?
Terrace/patio
Modern Lake Access Retreat. Hot Tub & Pet Friendly!

Modern Lake Access Retreat. Hot Tub & Pet Friendly!

Modern Lake Access Retreat. Hot Tub & Pet Friendly!
Huddleston
10.0 out of 10, Exceptional, (8)
"4.5 stars - great stay! The home is easy to find and not ridiculously far from grocery, dining, and entertainment. Hosts were commutative and made check in super simple. Our group especially enjoyed the large outdoor deck."
United States
Alicia R.
The price is HK$1,945
HK$4,672 total
includes taxes & fees
31 Dec - 1 Jan 2026
Modern Lake Access Retreat. Hot Tub & Pet Friendly!
Outdoor spa tub
1066 Joffrey - 3 Bedroom Home 1st Fairway at Mariners SML

1066 Joffrey - 3 Bedroom Home 1st Fairway at Mariners SML

1066 Joffrey - 3 Bedroom Home 1st Fairway at Mariners SML
2.5 star property
Bedford County
10.0 out of 10, Exceptional, (3)
"The stay was great although very short. "
United Kingdom
Zac W.
The price is HK$2,064
HK$5,102 total
includes taxes & fees
1 Jan - 2 Jan 2026
1066 Joffrey - 3 Bedroom Home 1st Fairway at Mariners SML
Indoor pool
#206 Pointe - 2 Bedroom Lakefront Condo at Mariners SML

#206 Pointe - 2 Bedroom Lakefront Condo at Mariners SML

#206 Pointe - 2 Bedroom Lakefront Condo at Mariners SML
Huddleston
10.0 out of 10, Exceptional, (4)
"On first floor, great location to beach/pool/market"
United States
AMANDA B.
The price is HK$2,072
HK$4,330 total
includes taxes & fees
31 Dec - 1 Jan 2026
#206 Pointe - 2 Bedroom Lakefront Condo at Mariners SML
Fridge, microwave, stovetop, dishwasher
#2400 Pointe - Studio Suite at Mariners SML

#2400 Pointe - Studio Suite at Mariners SML

#2400 Pointe - Studio Suite at Mariners SML
Huddleston
10.0 out of 10, Exceptional, (3)
"My brother and I stayed to do a little fishing. We had a good time and had lunch at Tiffany’s. We enjoyed our stay. "
United States
jesse h.
The price is HK$982
HK$2,145 total
includes taxes & fees
31 Dec - 1 Jan 2026
#2400 Pointe - Studio Suite at Mariners SML
Indoor pool
#344 Pointe - 2 Bedroom Lakefront Condo at Mariners SML

#344 Pointe - 2 Bedroom Lakefront Condo at Mariners SML

#344 Pointe - 2 Bedroom Lakefront Condo at Mariners SML
Huddleston
10.0 out of 10, Exceptional, (1)
The price is HK$1,787
HK$3,963 total
includes taxes & fees
12 Jan - 13 Jan 2026
#344 Pointe - 2 Bedroom Lakefront Condo at Mariners SML
Exterior detail
Reagan’s Retreat~ Farmhouse Cottage on 45 acres~Hot Tub, Fire Pit

Reagan’s Retreat~ Farmhouse Cottage on 45 acres~Hot Tub, Fire Pit

Reagan’s Retreat~ Farmhouse Cottage on 45 acres~Hot Tub, Fire Pit
Glade Hill
10.0 out of 10, Exceptional, (74)
"Peaceful, beautiful, clean, and the beds were super comfortable. It was exactly what we were looking for. "
United States
Nikki H.
The price is HK$804
HK$2,029 total
includes taxes & fees
4 Jan - 5 Jan 2026
Reagan’s Retreat~ Farmhouse Cottage on 45 acres~Hot Tub, Fire Pit
Stovetop, coffee/tea maker, cookware/dishes/utensils
#233 Pointe - 2 Bedroom Lakefront Condo at Mariners SML

#233 Pointe - 2 Bedroom Lakefront Condo at Mariners SML

#233 Pointe - 2 Bedroom Lakefront Condo at Mariners SML
Bedford County
10.0 out of 10, Exceptional, (5)
"Great location, great property, balcony was super nice!! Had Mother's Day Brunch, downstairs at Tiff's, it was excellent as well. Very nice stay!!"
United States
Jacqueline T.
The price is HK$2,072
HK$4,330 total
includes taxes & fees
31 Dec - 1 Jan 2026
#233 Pointe - 2 Bedroom Lakefront Condo at Mariners SML
Marina
#116 Pointe - 1 Bedroom Lakefront Condo at Mariners SML

#116 Pointe - 1 Bedroom Lakefront Condo at Mariners SML

#116 Pointe - 1 Bedroom Lakefront Condo at Mariners SML
Huddleston
10.0 out of 10, Exceptional, (4)
"Property was perfect. Very clean and comfy. The view was awesome. Would stay again."
United States
Phyllis O.
The price is HK$1,676
HK$3,428 total
includes taxes & fees
31 Dec - 1 Jan 2026
#116 Pointe - 1 Bedroom Lakefront Condo at Mariners SML
Exterior
Cozy Lakefront Condo with Kayaks at Bernard's Landing on Smith Mountain Lake

Cozy Lakefront Condo with Kayaks at Bernard's Landing on Smith Mountain Lake

Cozy Lakefront Condo with Kayaks at Bernard's Landing on Smith Mountain Lake
Moneta
10.0 out of 10, Exceptional, (35)
"We had a wonderful stay! Very peaceful and clean! "
United States
Sarah R.
The price is HK$818
HK$2,053 total
includes taxes & fees
11 Jan - 12 Jan 2026
Cozy Lakefront Condo with Kayaks at Bernard's Landing on Smith Mountain Lake
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.
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Top Pittsville Hotel Reviews

Hampton Inn Gretna - Smith Mountain Lake

Hampton Inn Gretna - Smith Mountain Lake

10/10 Excellent
"Thank you! I have stayed there since 2023 every year to visit family for the holidays. I have always been pleased with everything up and down! Keep up the great work! "
John 1-night trip
Posted 7 days ago
Hampton Inn Gretna - Smith Mountain Lake

Find out more about Pittsville

Search for holiday rentals in Pittsville on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsville using one of the methods below:

  • View our selection of featured holiday rentals in Pittsville
  • Use the map to find apartments and other holiday homes in the Pittsville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pittsville while they last

Look no further and take a look at our great range of rental properties in Pittsville!

Frequently asked questions

Are there holiday rentals in Pittsville?

Yes, there are holiday rentals close to the most popular sights in Pittsville, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pittsville has to offer?

Secluded Lakefront Cabin Resort: 5400sqft 6BR, 5ba: This holiday home rental outside of Pittsville is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What’s there to see and do in Pittsville?

While you're exploring the area, Leesville Lake and Smith Mountain Lake State Park are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Lakeside Marina and Lake Haven Marina.

What’s a holiday rental in Pittsville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pittsville. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for small groups.