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Holiday houses in Pittsylvania County

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Top-rated holiday rentals in Pittsylvania County

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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, 124 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
Apartment in Danville
4.95 out of 5 average rating, 198 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.

Guest favourite
The studio apartment features a spacious bed dressed in blue linens, complemented by a decorative area rug. A wooden sofa and a dining table with four chairs are arranged nearby. Kitchen appliances are neatly organized, with light-colored cabinetry and countertop space utilized efficiently.
Apartment in Pittsville
4.85 out of 5 average rating, 20 reviews

Garage-top studio, Bedford Co. near Leesville Lake

In the country, as quiet as possible in Southern Bedford County. This garage-top studio apartment is on Dannie’s private driveway, 200 yards down from the gate. Dannie also operates an AirBnB Lake house at mile marker 8 on Leesville Lake, just 2 hundred yards further down the driveway, all located on Dannie's 10 acre, forested retirement retreat. There is free access to our Leesville Lake boat ramp available with plenty of parking for a boat trailer and possibly limited access to our dock.

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.
Condo in Moneta
4.99 out of 5 average rating, 276 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, 74 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
4.96 out of 5 average rating, 227 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.

Top Guest favourite
A serene lakeside view is presented, showcasing a smoothly flowing body of water bordered by lush greenery. A dock is visible, with boats moored alongside. The sky is painted in soft blues and warm hues, reflecting the tranquil atmosphere of the setting.
Condo in Moneta
4.91 out of 5 average rating, 266 reviews

Dock Holiday at Bernard's Landing

Experience the water and mountain views at spectacular this 1 bedroom, 1 bath top floor corner condo in desirable Dockside section of Bernard's Landing. Guests enjoy all the amenities of Bernard's Landing including 2 outdoor and 1 indoor pool, Basketball, tennis and pickle ball courts,beach area, restaurant, fitness center and marina area with boat rentals. All pools and beach are short walk from the front door. Enjoy stunning views from the walk-out deck in this well-stocked condo.

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, 143 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!"

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, 70 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 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
4.91 out of 5 average rating, 139 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.

Guest favourite
Two blue armchairs are positioned in a bright living area, centered around a modern electric fireplace. A colorful red accent pillow contrasts with the blue fabric of the chairs. Light streams through the adjacent window, showcasing warm wooden flooring.
Home in Danville
4.93 out of 5 average rating, 15 reviews

Charming Farm House Right in Town!

Beautiful pastoral setting and walking distance to the Dan River walking and biking trails and to historic River Town. Also a short drive to the new casino! Lovely green views out all windows, and you get the whole house- very private- no neighbors on either side! Laundry facilities in main level and romantic fire circle with chairs to watch the sunset. Frequent deer sightings!

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, 188 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