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Holiday rentals in Pittsylvania County

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Top-rated holiday rentals in Pittsylvania County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A charming two-story home with a white exterior is set against a clear blue sky. A welcoming entrance with a wooden door is flanked by decorative elements. A brick pathway leads through a manicured lawn, surrounded by lush greenery, enhancing the inviting atmosphere.
Home in Danville
4.98 out of 5 average rating, 133 reviews

Historic Gem w amenities * Midweek Stay Discounts*

Experience the best of Danville in this beautifully remodeled 1920’s gem! *MID-WEEK STAY DISCOUNT OF $30 OFF STAYS OF 3 NIGHTS OR MORE SUN-THUR* * 4 Bedrooms * 2 Full Bathrooms * 5 mins to Danville Caesars Virginia Casino * 20 mins to Virginia International Raceway * 35 mins to Martinsville Speedway * Fully Equipped Kitchen * Beautiful Deck with string lights/ yard games * Fire pit with Adirondack Chairs * Free Disney+ Streaming * Driveway & Street Parking * Walk to Averett or Downtown Danville

Top guest favourite
Flat in Danville
4.96 out of 5 average rating, 207 reviews

The Historic Blessing House in Danville on Main

Located on historic Main Street, the home has central HVAC, is workspace friendly, w/ tv and walking distance to coffee shop/wine bar/restaurant/museum/ hospital. Averette Univ is 6 blocks. Casino 1 mi Queen bed, ceiling fan, window blinds, drapes, full floor mirror & walk-in closet. Full kitchen w/ ceiling fan, coffee, tea, Keurig, bottled water, disinfectant, sanitizer, and cooking essentials. Private Bath with shower, soap, shampoo, conditioner, hair dryer. Linens incl. W/D available.

Top guest favourite
An open living area features a stone fireplace with a mounted TV above and large windows that provide a panoramic view of the lake. A round glass dining table is set near the window, complemented by a cozy sofa and armchair, inviting relaxation and gatherings.
Apartment in Moneta
4.99 out of 5 average rating, 284 reviews

Fun Lake Getaway with Breathtaking Views

Fantastic getaway on beautiful Smith Mountain Lake! Enjoy stunning views on two sides of this top-floor, corner condo with a wrap-around deck and natural shade. It is perfect for a relaxing break or an adventure! Activities include boating (with guest docks), swimming (indoor and outdoor), pickle ball, working out, and relaxing in the hot tub, steam room or sauna! If you are working remotely, this quiet space includes a desk and high-speed wireless. The individual HVAC unit also has a UV light.

Top guest favourite
A charming cottage is set against a backdrop of lush greenery, featuring a well-maintained gravel pathway leading to its entrance. Two stories are visible, with red shutters framing the windows and a porch area adorned by a decorative lantern. The expansive yard invites a sense of tranquility.
Home in Gretna
5 out of 5 average rating, 79 reviews

Little Haven Cottage

Leave the demands of life and enter the peace of our Little Haven Cottage. Enter our rendition of an English cottage and enjoy watching local wildlife pass through the tranquility. Your stay will offer a repose and the ability to connect through a slow and quiet experience. Surrounded by the growing Amish community and stores where you can buy Amish food/goods. 45 min to Liberty University/ Lynchburg 40 min to Smith Mountain Lake Under 20 min to historic railroad towns Gretna/Chatham/Altavista

Top guest favourite
A charming lodge exterior is framed by a large tree, showcasing a cozy structure with a sloped roof and a brick chimney. Outdoor seating is arranged near a gravel area, inviting relaxation in a serene natural setting.
Home in Sandy Level
4.97 out of 5 average rating, 234 reviews

Antler Ridge Lodge

Only 3 miles from SMITH MOUNTAIN! Zip Code 24161. (There's another Sandy Level near NC.) It is well-stocked and waiting for your next get-a-way! Explore acres of yard, woods & creek. Leesville & SML beaches & boat launches are 9-30 miles away. Walk or ride 1/2-mi to the road's end at Leesville Lake. Horses/hikers/bikers are welcome along the 5-mi ridge of Smith Mt minutes away. Relax around a fire enjoying the starry sky or kick back in the comfortable lodge complete with a gas log fireplace.

Guest favourite
The exterior of the lodge is showcased, featuring a spacious deck with outdoor seating. The large windows highlight the inviting interior, surrounded by colorful fall foliage. A gravel pathway leads toward the entrance, inviting guests to explore the private retreat.
Home in Gretna
4.93 out of 5 average rating, 108 reviews

Gorgeous Lakefront Cabin Resort: 5400sqft 6BR, 5ba

Welcome to the Lake Bear Lodge family! 5,400sqft private lakefront resort w a gorgeous view feat: * King bed suite * 6br, 5 bath * Massive Game Room! ~21 Arcades!!! ~75in TV ~Ping Pong ~2-player B-ball ~Pool Table ~Shuffleboard ~Bar w BT Speaker * Massive main living room w 70in TV * Private Dock * Firepit * Loaded Kitchen w Coffee Station * Huge Deck * 2 Screened Porch Areas (1 in master) * 6 kayaks, paddleboat * 2 paddleboards for rent, ask for price * Whirlpool bathtub * Gas grill

Guest favourite
A cozy living area is highlighted by a comfortable sectional sofa and a coffee table adorned with magazines. Two mirrors reflect light from nearby windows, enhancing the openness of the space. A decorative wall accent adds a welcoming touch.
Home in Danville
4.95 out of 5 average rating, 151 reviews

Comfy 3BR w/ large basement, deck, W/D, wifi

Our family's best memories occurred here - so we're opening our doors to groups looking to make memories of their own. With 3 bedrooms, 5 beds and free parking, there's room for everyone. Our huge family room with sleeper sectional, office nook, back deck, large yard, WiFi, large TVs, and games are reasons to stay in - but if you venture out, we're 10 minutes from the riverwalk and parks. With modern farmhouse decor, Retreat on Rosemary says, "Welcome to the South, y'all!"

Guest favourite
A modern living area features a cozy sofa facing a stone fireplace. Large glass doors open to reveal expansive lake and mountain views. A dining table is positioned near the window, complemented by natural light and decorative accents throughout the space.
Apartment in Moneta
4.95 out of 5 average rating, 150 reviews

Bernard's Landing Bliss! Breathtaking Views

Come savor the breathtaking lake and mountain views and experience the best of Bernards Landing in this condo! Enjoy the best amenities - high end stainless appliances, big flat screen TVs, keypad door access – and the list goes on! River Rock Tiled Shower and Silestone Counters! Bernard’s Landing offers so much – 2 outdoor/1 indoor pool, hot tub, beach, gym, sauna, boat launch, courtesy dock, tennis, pickle ball, racquetball courts, The Landing Restaurant, and more!

Top guest favourite
The exterior of a charming single-story home features white siding, a grey roof, and two front entrances. A well-maintained lawn with green grass surrounds the house, and trees with autumn foliage provide a colorful backdrop. A paved walkway leads to the front doors.
Home in Gretna
4.99 out of 5 average rating, 74 reviews

Nellie's Nest

This adorable three bedroom is perfect for your stay in Gretna. Hit the sidewalks for a run or walk down to the best coffee shop around, The Pod. Take a quick 15 min drive to Smith Mountain Lake or visit the wineries just outside of town. Relaxed living at it's best here in small town Virginia! *More photos coming Common Destinations: Chatham Hall and Hargrave Military Academy - 12 mins Olde Dominion Agricultural Complex - 6 mins Liberty University - 36 miles

Top guest favourite
A lakehouse is framed against a vibrant sunrise, with soft hues of orange and pink reflecting on the tranquil water. The structure features a wraparound deck, and a slight mist hovers above the lake, enhancing the serene atmosphere of the secluded setting.
Home in Pittsville
4.95 out of 5 average rating, 198 reviews

Lakehouse on Leesville Lake in Bedford County VA

My late wife, Gail, & I came out of retirement to renovate this unique home with a completely new kitchen, vinyl plank flooring, new deck & new well in the Fall of 2019. This 3 bedroom lakehouse is very secluded within about an hour drive from Lynchburg, Roanoke or Danville. The dock and boat ramp are especially convenient. Keep an eye out for eagles, osprey, deer, bear, turkeys, otters, geese & heron.

Top guest favourite
A red barn-style house is situated amidst green grass and trees. A stone chimney rises from one side, while a fire pit with seating is positioned nearby. A separate building is visible in the background, contributing to the rural setting.
Farm stay in Union Hall
4.92 out of 5 average rating, 145 reviews

Pine Haven Farms

Make memories at this unique and family-friendly place. Pine Haven Farms is a working farm. Spread out and enjoy the pastoral surroundings. We are located less than two miles away from Magnum Point Marina at Smith Mountain Lake if you want to add some lake time to your vacation stay. Please be aware that electric fencing is used for the cattle. Children should be supervised at all times.

Top guest favourite
The image captures a fountain with multiple streams of water, set against a backdrop of a brick building with a vibrant awning. Outdoor seating is visible at a restaurant, surrounded by greenery and park space.
Loft in Danville
4.97 out of 5 average rating, 194 reviews

2BR Riverview Fountain Loft - Best Location!

BEST LOCATION! 2 BR River District Loft in the very heart of downtown. River and Fountain Park views. Popular local restaurant downstairs and many more within short walking distance as well as Ballad Brewery and Riverwalk access and a Bikeshare station within 50 yards. Great for VIR, Averett University, Caesar’s Casino and Corporate visits.

Popular amenities for Pittsylvania County holiday rentals