Holiday rentals in Pittsylvania County

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Top-rated holiday rentals in Pittsylvania County

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Guest favourite
A charming cottage-style home features a pastel pink front door, flanked by two symmetrical windows with classic shutters. The entryway is approached by a stone pathway leading up from a landscaped front yard, enhancing the welcoming appearance of the property.
Home in Danville
4.95 out of 5 average rating, 21 reviews

Lover’s retreat, walk to casino

Enjoy a trip away from your worries and strife by relaxing in this stylish couples haven that feels like stepping into your cottage Pinterest board. What better way to spend time away from home than in a spacious, artist-endowed retreat, far away from clutter, chores, and stress? Slip into a comfy bathrobe after a warm bath to watch tv, fall asleep listening to green noise, or enjoy coffee on the front porch. Ideal for longer stays- discounts applied. Extra linens and cleaning products supplied.

Top guest favourite
Flat in Danville
4.96 out of 5 average rating, 214 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 inviting indoor pool area features a clear blue water pool, surrounded by large windows that allow natural light to fill the space. A vibrant mural of mountains and water adds a serene backdrop, while a poolside ladder provides easy access.
Apartment in Moneta
4.99 out of 5 average rating, 291 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.

Guest favourite
Aerial view captures a modern condo complex beside a sparkling pool, surrounded by lush greenery. The inviting pool area features comfortable lounge chairs positioned around the water, and the serene landscape showcases trees and paths leading towards the nearby lake.
Apartment in Moneta
4.98 out of 5 average rating, 116 reviews

Tranquility Cove Condo at Smith Mountain Lake

—We Welcome You— Visit and experience the ultimate respite while enjoying amazing water and mountain views, sunrises, and sunsets. This ground level condo is perfectly situated in Bernard's Landing Resort on beautiful Smith Mountain Lake! This bright, stylish & thoughtfully appointed space welcomes you to a full kitchen, spacious bdrm w/king bed, walk-in shower, and a queen sleep sofa. Amenities include restaurant & bar, tennis, pickle ball, gym, sauna, hot tub, three pools and a sandy beach.

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, 83 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, 239 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 walk-out deck overlooks the lush green lawn and serene water views. A small round table is paired with two comfortable chairs. Nearby, the exterior of a neighboring building is visible, complementing the tranquil setting.
Apartment in Moneta
4.91 out of 5 average rating, 275 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
4.94 out of 5 average rating, 157 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
An indoor pool is surrounded by white columns, featuring a mural of mountains and a lake on the wall. Several chairs are positioned along the edge of the pool area, with potted plants adding a touch of greenery.
Apartment in Moneta
4.91 out of 5 average rating, 211 reviews

Lake Escape - Smith Mountain Lake Condo

Located in Bernard's Landing, SML, this ground-floor condo offers everything you need for a quick getaway or a week-long vacation. The condo has recently been re-decorated and offers beautiful lake views, convenient access to boat rentals, one of the best restaurants on SML (Napoli by the Lake), and all the amenities you need. Guests have access to indoor and outdoor pools (outdoor pools open seasonally), sandy beach area, sauna, gym, and tennis and pickle ball courts.

Guest favourite
An outdoor pool area features a protective cover, with a compass design set into the pavement. Surrounding greenery and residential buildings are visible in the background, with tennis courts as a nearby amenity.
Apartment in Moneta
4.95 out of 5 average rating, 151 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
A bright living area features a comfortable sofa and two armchairs arranged around a glass coffee table on a patterned area rug. Natural light filters through the windows, enhancing the space, while a modern ceiling fan adds functionality. Artwork is displayed on the wall.
Home in Danville
5 out of 5 average rating, 38 reviews

Chic 2Br/1Ba Home near Downtown & Caesars Casino!

This contemporary styled home, nestled in a quiet neighborhood, is perfect for extended business stays and family, couples or friend getaways. Enjoy quick access to explore Danville's Historic River District sites, trails, museums, restaurants and much more! Downtown Historic River District: 3.4mi Caesar's Virginia Casino: 5.5mi VIR (Virginia International Raceway): 17.5mi Martinsville Speedway: 33mi Liberty University: 59mi

Top guest favourite
A spacious upper deck features a propane grill, a round table with an umbrella, and two chairs, all overlooking a serene lake view. The railing borders the deck, complemented by a decorative lantern that adds subtle charm.
Home in Pittsville
4.95 out of 5 average rating, 200 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.

Popular amenities for Pittsylvania County holiday rentals