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Top Holiday Rentals in Pittsville

Private house on Leesville Lake

10.0 out of 10, Exceptional, (31)
"Wonderful stay."
Private house on Leesville Lake

Stylish Creekside Cabin w/ Fire Pit Near Wineries

10.0 out of 10, Exceptional, (54)
"Very nice and very private. Would definitely stay here again."
Stylish Creekside Cabin w/ Fire Pit Near Wineries

Treetop & Waterfront! Quiet Cove, Hot Tub, Kayaks, Game Room and more

10.0 out of 10, Exceptional, (52)
"Wonderful!"
Treetop & Waterfront! Quiet Cove, Hot Tub, Kayaks, Game Room and more

Secluded Waterfront Get Away on Smith Mountain Lake

9.8 out of 10, Exceptional, (161)
"Beautiful location and one of the cleanest houses we have stayed in. Overall excellent experience and can’t wait to return."
Secluded Waterfront Get Away on Smith Mountain Lake

Romantic SML Penthouse, Bernard’s Landing. Smith Mountain Lake 3 Pools

10.0 out of 10, Exceptional, (292)
"We loved our stay here! Everything was exactly as described and pictured. Would definitely come back! "
Romantic SML Penthouse, Bernard’s Landing. Smith Mountain Lake 3 Pools

Waterfront Condo at Stripers Landing, Smith Mountain Lake, Virginia

9.6 out of 10, Exceptional, (63)
"We love coming to this area for our sml trips. Its kid friendly with the pool and easy access to the lake."
Waterfront Condo at Stripers Landing, Smith Mountain Lake, Virginia

5 Bed 4 Bath Waterfront Home on Deep Water Cove Ideally located by car or boat!

9.8 out of 10, Exceptional, (196)
"Stunning home on Smith Mountain Lake. Our group of friends came and had a restful weekend away. Loved the kayaks, multiple bedrooms and bathrooms, and the view! The host was AMAZING with communication and was incredibly kind. Highly recommend this house!"
5 Bed 4 Bath Waterfront Home on Deep Water Cove Ideally located by car or boat!

Lakefront home for easy boating, fishing, private dock & AC/Wifi, Dogs ok!

9.0 out of 10, Wonderful, (24)
"Enjoyed our stay! Family of 5 - house is well described in the listing. We fit comfortably in the house; rented a boat and jet ski and used the kayaks and could easily get out on the lake from this great location; nice kitchen table for evening board games and lovely porch for morning tea!"
Lakefront home for easy boating, fishing, private dock & AC/Wifi, Dogs ok!

Unique cabin that sits right on the water. Huge deck. Amazing views. Gas grill.

9.4 out of 10, Exceptional, (78)
"The title says it all, the water view we're incredible to wake up to every morning and the over all feel of the property was very comfortable. We had a great stay!"
Unique cabin that sits right on the water. Huge deck. Amazing views. Gas grill.

Lovely studio at Mariners Landing!

9.8 out of 10, Exceptional, (58)
"It worked well for our quick stay"
Lovely studio at Mariners Landing!

Bernard's Landing Bliss! - Breathtaking Views & Modern Updates

10.0 out of 10, Exceptional, (252)
"Great location, clean and close to restaurants…loved the fireplace and the ease of check in and check out. "
Bernard's Landing Bliss! - Breathtaking Views & Modern Updates

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

10.0 out of 10, Exceptional, (3)
"Really enjoyed the stay. Plenty of room to spread out inside and out, with a great dock. We enjoyed the paddle boards, as well as ice cream just a short walk away at the marina. We would definitely return!"
Charming SML lake front 3-bedroom house with WiFi and AC in beautiful Huddleston

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

9.8 out of 10, Exceptional, (22)
"My family and I had a great time here! I would rent this house again! Accommodations were great! We really loved the water! Maybe hard to get to the water if handicapped!"
Shangri-La -dogs friendly, firepit, wifi, 2 kayaks, 2 kitchens, and a Pool Table

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

9.6 out of 10, Exceptional, (10)
"My family and I stayed here for a long Memorial Day weekend. It was clean, and so welcoming. The lake is beautiful and we loved being able to fish and jump in from the dock. The hot tub was amazing and clean. We had the best time and loved every bit of our stay. Would highly recommend and would stay there again!"
Hot tub, Dock, Fire Pit, Dog Friendly, Golf,

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

10.0 out of 10, Exceptional, (273)
"The cabin was super cozy and fun. We had a lot of fun swimming and playing on the dock and enjoying the hammocks and scenery."
Unique Historical log cabin with private beach and 300 ft. of waterfrontage.

Private pool and hot tub, paddleboard, ping pong

10.0 out of 10, Exceptional, (1)
"The house was beautiful with an amazing view. Spent a long of time on the dock swimming in the clean, clear lake and sitting by the pool. Would definitely come back!"
Private pool and hot tub, paddleboard, ping pong

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

2.0 star property
8.4 out of 10, Very good, (6)
"My family and I had a wonderful stay. The scenery was gorgeous and the amenities were great! Would highly recommend!!"
Splendid dog friendly home with shared pool, kayaks & free WIFI

Belview Bay Condo, Best Sunsets Ever

9.4 out of 10, Exceptional, (75)
"Clean, comfortable and equipped with everything we needed. A lovely place to stay."
Belview Bay Condo, Best Sunsets Ever

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

9.8 out of 10, Exceptional, (22)
"Cute one bedroom on Smith Mountain Lake."
The price is £260
includes taxes & fees
1 Jul - 2 Jul
Cozy Lakefront Condo with Kayaks at Bernard's Landing on Smith Mountain Lake

Recently updated 1 BR Condo with stunning lake views - No cleaning or linen fees

10.0 out of 10, Exceptional, (151)
"The condo was great. Very clean with a great location and lake views. Todd was very accommodating. "
Recently updated 1 BR Condo with stunning lake views - No cleaning or linen fees
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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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?

5 Bed 4 Bath Waterfront Home on Deep Water Cove Ideally located by car or boat!: This holiday home rental outside of Pittsville is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 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 Palmer's Marina and Smith Mountain Lake.

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.