Holiday Rentals in Pittsylvania County

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Featured Holiday Rentals in Pittsylvania County

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

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

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

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!

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.

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!

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

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.

Smith Mountain Lake Retreat w/ Private Beach!

7.0 out of 10, Good, (8)
"Was a nice place to get away for a weekend. Had a homey feel. Very nice private location and view of the lake."
Smith Mountain Lake Retreat w/ Private Beach!

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 €308
includes taxes & fees
30 Jun - 1 Jul
Cozy Lakefront Condo with Kayaks at Bernard's Landing on Smith Mountain Lake

Cozy Waterfront Cottage -- Cabin 7 Cedar Key, No Wake Cove, Great Views!

9.6 out of 10, Exceptional, (202)
"Perfect trip within a 2-3 hour drive time Beautiful landscape and cabin vibe"
Cozy Waterfront Cottage -- Cabin 7 Cedar Key, No Wake Cove, Great Views!

Spacious pet friendly house w/hot tub, kayaks, air hockey, deck & patio

Spacious pet friendly house w/hot tub, kayaks, air hockey, deck & patio

Foothills Retreat, New Lakefront Luxury w/ Covered Decks + Hot Tub, Fire Pit Terrace, Dock & More!

9.6 out of 10, Exceptional, (71)
"Can’t ask for a better stay. We have stayed at two of GateWays properties within a month on purpose. They’re built by someone that understand lake life. Relaxed and luxury for a vacation. Special owners to understand the dynamics of a quiet cove. "
Foothills Retreat, New Lakefront Luxury w/ Covered Decks + Hot Tub, Fire Pit Terrace, Dock & More!

Whispering Pines Estate, Waterfront Luxury w/ Covered Verandas + Heated Salt Pool, Hot Tub, Dock!

10.0 out of 10, Exceptional, (5)
Whispering Pines Estate, Waterfront Luxury w/ Covered Verandas + Heated Salt Pool, Hot Tub, Dock!

Waterfront Condo!

9.8 out of 10, Exceptional, (44)
"This place was perfect for our stay. Cute and cozy!"
Waterfront Condo!

Sweet By and By... Your Escape to the Beauty of Smith Mountain Lake

9.8 out of 10, Exceptional, (158)
"Our trip was very enjoyable. The Sweet By & By was very clean, very cozy, beautiful view, and just overall very relaxing."
Sweet By and By... Your Escape to the Beauty of 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.
Save an average of 15% on thousands of hotels when you're signed in