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Holiday rentals in Pittsylvania County

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Pittsylvania County

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

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Guest favourite
A spacious living area is furnished with a dark sectional sofa and a wooden coffee table atop a neutral area rug. Light fixtures hang from the ceiling, and a warm welcome sign is mounted on the wall. The open layout provides a view into the dining space.
Home in Alton
4.94 out of 5 average rating, 198 reviews

8 mi. to VIR! 18 min to Danville, South Boston, Va

Spacious, clean, & relaxing, this home is less than 8 miles from VIR and 18 mi to Danville, South Boston, or Roxboro. The listing is on one floor level to accommodate those with mobility issues. High-speed Starlink WiFi. Bedrooms provide linens/pillows/blankets. Bathrooms provide towels & necessities. Full kitchen w/coffee. Oversized paved parking with easy accessibility. Perfect for trailers/multiple large vehicles. Close to hwy, may want to pack earplugs. Strict no smoking or pets please.

Top guest favourite
Flat in Danville
4.96 out of 5 average rating, 223 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
A welcoming entryway features an archway leading to a cozy living area, illuminated softly from a nearby lamp. Framed botanical art adorns the walls, alongside decorative plants in stylish pots. A neutral rug adds warmth and texture to the wooden floor.
Home in Danville
5 out of 5 average rating, 101 reviews

BRAND NEW! Charming 2 Br home...great location!!!

Perfectly nestled in a quiet, safe neighborhood! Centrally located near the downtown River District and Riverwalk Trail, Averett Univ., SOVAH Health and great restaurants. Professionally renovated, decorated and landscaped with attention to details to make your stay comfortable and enjoyable! Screened porch for coffee and birdwatching, fresh herbs and flowers for cutting, great internet for home office and smart tvs in every room. Well supplied throughout to make the perfect home away from home

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, 106 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. 

Guest favourite
The image showcases different areas of the home. A cozy living room with a smart TV and seating is visible alongside a modern kitchen with ample counter space. A dining nook features a round table with decor. A game room highlights entertainment options, including a dartboard and a mini-golf setup.
Home in Danville
4.91 out of 5 average rating, 121 reviews

Central Retreat with Gameroom Near Casino

Enjoy the comfort and convenience of our spacious home, perfect for both short getaways and extended stays. It is only 5 minutes away from Caesars Casino and 30 minutes away from VIR. Our property is equipped with modern amenities you need for a comfortable and productive stay, including: * High-speed Wi-Fi * Dedicated workspace * Smart TVs in all bedrooms * Sound system (Bluetooth) in living rooms * Game room * BBQ grill Message me about weekly or extended stay discount.

Guest favourite
Flat in Danville
4.97 out of 5 average rating, 118 reviews

Chic Haven: 2b/1bath in the Heart of Danville

Welcome to our chic and charming boutique-inspired Airbnb nestled in the heart of the Old West End, just steps from Downtown Danville. Designed with a passion for style and comfort, our space offers a unique blend of luxury and personality, curated to provide you with an unforgettable stay. While there are stairs, the privacy that you'll find on your front and back patios is unmatched! You'll be able to enjoy your morning coffee with a private view. STR Permit# PZ25-00015

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
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, 79 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
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, 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, 201 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, 159 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.

Popular amenities for Pittsylvania County holiday rentals