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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Guest favorite

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, 205 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.

LocationFamilyNearby

Top guest favorite

A cozy sleeping area features a spacious bed dressed in soft linens, with a layered throw blanket and decorative pillows. Large windows offer views of the surrounding forest, while natural wood paneling and a light fixture enhance the serene ambiance.

Tiny home in Union Hall

4.98 out of 5 average rating, 65 reviews

BelleTerre Luxe Havens in Forest-Maple

Meet "Maple", your serene sanctuary immersed in nature. She’s designed to soothe your soul with nature-inspired tones and luxurious simplicity. Wake up wrapped in soft linens and down duvets, surrounded by towering trees and the sounds of nature. Lounge in bed while watching the wildlife, soak in the standalone tub, and unwind on your private deck with a grill, hammock, and firepit. Whether you’re here to reconnect with yourself or a loved one, Maple welcomes you with warmth, comfort, and peace.

FamilyLocationHiking

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.

ValueLocationLong stay

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, 135 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

ValueFamilyGetting around

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, 109 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!

LocationValueIndoor spaces

Top guest favorite

The exterior of the cottage is set against a backdrop of lush greenery. A covered porch invites relaxation, with seating available on both the porch and around a stone fire pit. A pathway leads to the entrance, surrounded by trees for privacy.

Cottage in Penhook

5.0 out of 5 average rating, 30 reviews

The Cottage on Locust Lane, Waterfront On SML

Nestled in the serene woods overlooking the beautiful waters of Smith Mountain Lake, The Cottage on Locust Lane offers the perfect blend of tranquility and opportunities for fun on the lake. Our charming cottage is located in a peaceful cove at the foot of Smith Mountain in Penhook, Virginia. Smith Mountain Lake has earned the title "The Jewel of the Blue Ridge Mountains" and our cottage is the perfect location to relax, have fun, and experience all our beautiful lake has to offer.

LocationFamilyIndoor spaces

Guest favorite

Home in Danville

4.86 out of 5 average rating, 22 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.

LocationFamilyQuiet

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.

FamilyValueView

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, 87 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

FamilyLocationCondition

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!

LocationFamilySleep quality

Top guest favorite

The home features a brick exterior with white shutters and a covered front porch. A sloped grassy yard leads to a stone walkway. Large windows allow for natural light, creating an open and welcoming entrance.

Home in Danville

4.97 out of 5 average rating, 71 reviews

Cozy Danville Retreat- updated game room!

Bring the whole family to this great place with lots of room for fun. Welcome to our inviting 3-bedroom, 2-bath home in beautiful Danville, VA! Perfect for families, groups, or business travelers, our spacious and stylish home offers all the comforts you need for a relaxing stay. Enjoy a blend of modern amenities and Southern charm in a quiet neighborhood just minutes from downtown.

FamilyLocationIndoor spaces

Guest favorite

The living room features a comfortable black leather sofa and a classic armchair with a patterned design. A coffee table sits centrally on a patterned area rug, while a TV is mounted on the wall. Natural light enters through the windows, enhancing the space.

Home in Danville

4.94 out of 5 average rating, 106 reviews

The Empty Nest

Located just 2.7 miles from Caesars Virginia and 2 miles from the NC state line, the Empty Nest is your perfect getaway. With Virginia International Raceway 20 miles away and Martinsville Speedway just 30 miles, it's an ideal base for both adventure and relaxation. Enjoy the comfort and convenience of this charming retreat!

ValueFamilyCheck-in