
Holiday rentals in Pittsylvania County
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Top-rated holiday rentals in Pittsylvania County
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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.

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

Roark Mill Retreat
Welcome to the Roark Mill Retreat. Your cozy and private getaway located in the bottom level of our charming home on Roark Mill Road in Hurt, VA. This inviting space offers a comfortable queen bed along with a queen/twin bunk bed. We offer a well equipped kitchenette and a refreshing bathroom. Enjoy the convenience of a separate entrance and the tranquility of a peaceful neighborhood. Whether you’re here for one night or a longer stay, you’ll find everything you need for an enjoyable visit.

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!

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.

Lake Lover's Paradise
Come to the lake! This spacious one bedroom top floor end unit is uniquely located between Napoli by the Lake restaurant and large outdoor swimming pool. Fantastic views of the lake from the large deck! Sleeps 2 adults and 2 small children under three. The following amenities are provided during your stay (Subject to season and repair): 2 Outdoor Pools Exercise Room Boat & Jet Ski Rental 1 Indoor Pool Hot Tub Courtesy Boat Slips Beach & Boat Launch Area Tennis & Pickleball Courts

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.

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

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!

Central, Stylish 3/2 Family Home + Great Amenities
This very recently renovated home is one of the most stylish, comfortable and luxe Airbnb's to be had in the area. With 3 bedrooms and 2 bathrooms, there is more than enough space for six guests! All the furniture and furnishings are new and you have everything you need to be safe, comfortable, productive and entertained. Whether you're into reading, enjoying Netflix, journaling or cooking in the chef's kitchen, this is the perfect place for you!

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.

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
Other great holiday rentals in Pittsylvania County

Little House at Leesville Lake

Cozy cottage

Lake Haven - Hot Tub! Mountain Views!

Terrapin Station

The Owl House

Rough camping

We have water! Spacious with Gentle Slope and Dock

Hickory Forest Hideaway
Destinations to explore
- Rentals with pools Pittsylvania County
- Rentals with outdoor seating Pittsylvania County
- Pet-friendly rentals Pittsylvania County
- Rentals with lake access Pittsylvania County
- Rentals with beach access Pittsylvania County
- Rentals with a kayak Pittsylvania County
- Fitness-friendly rentals Pittsylvania County
- Apartment rentals Pittsylvania County
- Beachfront rentals Pittsylvania County
- House rentals Pittsylvania County
- Waterfront rentals Pittsylvania County
- Rentals with a firepit Pittsylvania County
- Rentals with a patio Pittsylvania County
- Flat rentals Pittsylvania County
- Rentals with a fireplace Pittsylvania County
- Rentals with a hot tub Pittsylvania County
- Family-friendly rentals Pittsylvania County
- Rentals with a washing machine and dryer Pittsylvania County
- Smith Mountain Lake State Park
- Hanging Rock State Park
- Greensboro Science Center
- Virginia International Raceway
- Elon University
- Fairy Stone State Park
- International Civil Rights Center & Museum
- Liberty Mountain Snowflex Centre
- Guilford Courthouse National Military Park
- National D-Day Memorial
- Amazement Square
- Martinsville Speedway
- Mill Mountain Zoo
- Explore Park
- Percival's Island Natural Area
- Taubman Museum of Art
- Mill Mountain Star
- Tanger Family Bicentennial Garden
- Virginia Museum of Transportation
- Harvester Performance Center
- Greensboro Country Club
- SeaQuest Lynchburg





