Vacation rentals in Pittsylvania County

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Top-rated vacation rentals in Pittsylvania County

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

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Top guest favorite
Apartment in Danville
4.96 out of 5 average rating, 233 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 favorite
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, 134 reviews

Cute and Comfy Cabin, Stunning Lakefront Views,

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 & 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.  See Notes

Guest favorite
A wooden dock extends over a calm lake, leading to a covered area where people can relax. The surface of the water reflects the soft blues and warm hues of the sky, with mountains visible in the background, enhancing the serene atmosphere.
Home in Bedford County
4.93 out of 5 average rating, 28 reviews

Hycliff Lodge - water access

Enjoy the nature and tranquility of this private, 5 acre mountain home on Leesville Lake. Hycliff offers comfortable sleeping for 6 with 3 bedrooms and 2 full bathrooms. The open floor plan, cozy furnishings and a plethora of entertainment are sure to make some core family vacation memories. Hiking and fishing lovers are sure to enjoy the challenging, 1/10 mile walk to the water to your private, covered dock. The mountain and sunset views are stunning all year long from this gorgeous property.

Top guest favorite
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
4.93 out of 5 average rating, 108 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 favorite
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, 123 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 and 2 kayaks 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 favorite
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, 208 reviews

Lakehouse on Leesville Lake in Bedford County VA

This secluded, 3 bedroom lakefront home was renovated In 2019. My late wife Gail and I installed a new kitchen, vinyl plank flooring, new well, and new decks (both wraparound and lower deck.) The home is located about an hours drive from Lynchburg, Roanoke or Danville. Enjoy our private dock and boat ramp for fishing, watercraft, swimming, and nature watching! Keep an eye out for wildlife, both great and small! Great Blue Herons, Eagles and Osprey are personal favorites!

Guest favorite
Home in Danville
4.86 out of 5 average rating, 21 reviews

Cozy cottage

Stay at this beautifully renovated, 1940s cottage, right on the outskirts of Danville. Perfectly placed on a calm street, you will be able to relax while only being 5-10 minutes from all stores and attractions. The space is cute and cozy with everything you need to feel right at home! **PLEASE READ** This home was built in the 1940s. The ceilings are low. Most rooms are around 7 ft. The living room is 6’ 8”. If you are a taller person, the ceiling height may be uncomfortable.

Top guest favorite
Home in Chatham
5.0 out of 5 average rating, 33 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 favorite
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
4.98 out of 5 average rating, 86 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 favorite
Aerial view of the cabin and pool area, surrounded by lush green trees and well-maintained gardens. A rectangular pool is centrally located, flanked by colorful umbrellas alongside sun loungers. The rustic cabin and neighboring structures feature varied roof styles, contributing to the serene country setting.
Farm stay in Hurt
4.97 out of 5 average rating, 119 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!

Guest favorite
Home in Huddleston
4.97 out of 5 average rating, 181 reviews

Diving Board, Waterslide, Private, Lakefront

Welcome to this peaceful & private 1-acre A-Frame lakefront escape on stunning Smith Mountain Lake, VA! Enjoy sweeping wide-water views, breathtaking sunsets, and mountain vistas from four serene outdoor living spaces. Jump in the crystal clear lake from the dock’s diving board, race down the waterslide, or just relax in total privacy. Peaceful, fun, and unforgettable, this is lake life at its best!

Top guest favorite
Farm stay in Union Hall
4.93 out of 5 average rating, 169 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.

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