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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
Home in Danville
4.92 out of 5 average rating, 142 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 nestles among vibrant blooming trees, with soft pink blossoms contrasting against the green landscape. The structure features light-colored siding with brick accents, surrounded by lush grass and a gravel drive, offering a peaceful country setting.
Home in Sandy Level
4.97 out of 5 average rating, 248 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
A market sign hangs from a building, featuring the name 'Midtown Market' in bold letters. An American flag is displayed prominently beside the entrance, and the structure showcases horizontal wooden siding with a covered awning. The background features a hint of greenery and a clear sky.
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
The entrance is framed by columns, featuring a welcoming red door. Potted plants adorn the porch, accompanied by several chairs on both sides. The pathway is lined with fresh mulch and greenery, providing a charming entrance to the home.
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
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
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 exterior of a historic building is illuminated at night, featuring large windows and a welcoming entrance. A striking red armchair is positioned prominently in the entryway, creating a vibrant focal point against the neutral tones of the façade.
Apartment in Danville
4.98 out of 5 average rating, 42 reviews

1 BR suite - River District - full kitchen

Welcome to the former Nabisco building! Reincarnated as short-term lodging, this 1 BR suite is the best of historic building rehabs with modern amenities. Enjoy complimentary coffee, bottled water, snacks and the best the River District has to offer. Conveniences such as wifi, a full kitchen, and in-unit laundry are at your fingertips to enhance your stay. Enjoy street and courtyard views in a luxurious suite with bars, restaurants, and the casino just minutes away from the front door.

Guest favourite
A cozy living area features a modern flat-screen TV mounted on a dark gray wall, above a fireplace. Two green chairs frame a low wooden coffee table on a textured area rug, creating a relaxed setting. Natural light from an adjacent space enhances the warmth of the room.
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.

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.

Top guest favourite
A modern kitchen features a wood countertop paired with white cabinetry and stainless steel appliances. Two framed botanical prints hang above the dual sinks, providing a subtle decorative touch. Natural light illuminates the space through the window, enhancing the warm wood flooring.
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
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 spacious, wooden lower deck is shown, overlooking a calm lake. A grill is positioned at the deck's edge, with a railing surrounding the area. In the background, a dock with a swimming ladder and parked boats is visible, framed by wooded shores.
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.

Popular amenities for Pittsylvania County holiday rentals