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 small kitchen area features a black dining table surrounded by four wooden chairs. A coffee station is visible on the wall, with coffee cups and a coffee maker arranged neatly. Natural light enters through the window adorned with floral curtains.
Home in Danville
4.91 out of 5 average rating, 140 reviews

Quaint & Quiet Place 10 miles from VIR

Comfortable and relaxing, this older 3-bedroom home sits on 1.5 acres with large shade trees. Both front porch and back deck areas have peaceful views. Very safe, quiet neighborhood. The circle drive extending in front of the house adds extra paved parking for trailers, etc. VIR guests welcome! Under 10 mi to VIR. Less than 1 mi. to Danville Airport & dining, and 5 mi. to historic downtown Danville and the hospital, and 8 mi to Casino. Prime location to Danville. Very fast, high-speed WIFI.

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, 246 reviews

Antler Ridge Lodge - 19 Acres of Seclusion +WiFi

Only 12-mi to the Anthony Ford Boat Launch at SML, 8-mi to Myers Creek ramp at Leesville Lake. Well-stocked and waiting for your next get-a-way! Explore acres of yard, woods & creek. Leesville Lake only a 1/2-mi walk to the end of the road. Horses/hikers/bikers are welcome along the 5-mi ridge of Smith Mt only 3-mi away. Relax around a fire enjoying the starry sky or kick back in the comfortable lodge complete with a gas log fireplace, 65" Smart TV, & Fiber WiFi, 50 MBS up & down. Pet friendly.

Top guest favourite
Flat in Danville
4.96 out of 5 average rating, 222 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
Lush green trees frame a serene body of water, reflecting a clear blue sky. The view includes a modern house with a porch, positioned by the water's edge, creating a peaceful lakeside atmosphere.
Bungalow in Penhook
4.95 out of 5 average rating, 119 reviews

Scenic Lake Getaway

Awesome walkout basement apartment in a new home that is perfect for couples. Wake up to emerald waters and picturesque Smith Mountain view from the comforts of your bed. Full kitchen and dining as well as a furnished outdoor patio space with hot tub. The is an outdoor grill fire pit. A pontoon boat, 2 stand up paddleboards , 2 kayaks and a jet ski are available to rent. You are welcome to share the dock with us! It's a number of steps to get to the water, but well worth the walk back up.

Top guest favourite
A modernized cabin is set in a serene natural environment, surrounded by green grass and trees. A covered porch is featured at the front, with rocking chairs and a porch swing positioned for relaxation. A pathway leads to the cabin, enhancing accessibility.
Cabin in Long Island
4.92 out of 5 average rating, 105 reviews

100acre Woods Cabin Retreat

No Smoking in home, No animals or pets allowed! 30 mi to Lynchburg, 11 to Altavista. This cabin boasts 100 acres of serene nature while hiking the trails, fishing and swimming in the river. Canoe from the boat slip down river to the long Island community center. Relax on the large rocking chair front porch with your honey on the porch swing, or roast marshmallows and sip drinks around the fire pit! This is not a party house, it is meant to relax and enjoy peace, quiet, and nature, enjoy!

Guest favourite
A cedar cabin is set against a backdrop of serene water and mountains, with vibrant pink blooms in the foreground. The tranquil scene is enhanced by lush greenery surrounding the cabin, providing a peaceful lakefront atmosphere.
Cabin in Huddleston
4.9 out of 5 average rating, 126 reviews

Cute and Comfy Cabin

Every season offers something special be it summer on the water, fall foliage, cozy winters by the electric fireplace, and blooming springs.   Book your stay and experience why guests return year after year. Wake up to panoramic lake and mountain views in a peaceful, no-wake 60 acre cove, perfect for fishing, relaxing, reconnecting, and making memories. Inside, this cabin you’ll find a playful bear-themed décor that guests of all ages love—adding a fun, memorable touch to your stay. 

Top guest favourite
Home in Chatham
5 out of 5 average rating, 30 reviews

Hermione’s Purse

In the heart of downtown Chatham just across the creek from Chatham Hall, you will find a tiny home with room for everyone. Private and quiet with sweeping green views, Hermione’s Purse is within easy walking distance of both private schools and all downtown businesses. Built to last in 1960, the original part of the home consists of the living room and kitchen, with two bedrooms upstairs. The home’s first indoor bathroom and a bedroom downstairs were added in the 1980s.

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, 165 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
Farm stay in Hurt
4.97 out of 5 average rating, 116 reviews

18th Century Cabin Retreat

Come enjoy our 18th century cabin! They don't make them like this anymore. One side built in 1750, the other in 1825. Sit under the giant white oak and enjoy the country air. This is a wonderful retreat to kick back and relax. Enjoy the pool, horseshoes, and fire pit. In the winter months, cozy up by the wood stove or fire place with gas logs. NO PETS!!! Please do not bring your pets. Owners live on site, so if you are in need of anything, please ask!

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, 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.

Top guest favourite
Farm stay in Union Hall
4.92 out of 5 average rating, 158 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 exterior of a renovated log cabin is visible, featuring a green metal roof and white siding. A welcoming porch with two chairs is seen, framed by seasonal pumpkins. Tall trees and a neatly maintained yard create a serene rural setting.
Cottage in Danville
4.97 out of 5 average rating, 292 reviews

The Home House at Belle Farm

Built in 1932 as a log cabin, this completely renovated farm house is set in a peaceful rural setting. This cozy cottage has all modern amenities but maintains its character and charm, with nostalgic nods to its tobacco farm roots. Set on a 35 acre farm, chickens will be your neighbors.

Popular amenities for Pittsylvania County holiday rentals