Holiday rentals in Pittsylvania County

4.96 out of 5 average rating, 81 reviews

Guest suite in Chatham

Mahalo Suite...beach vibes in Virginia foothills

Keep it simple at this 438 sq ft peaceful and centrally-located place in the heart of Chatham, VA. Within walking distance to Chatham Hall and Hargrave and our local coffee shop and restaurants. Conveniently located 25 minutes from Danville and 45 minutes from Lynchburg and a 5Smith Mountain Lake State Park is about 45 minutes from here which offers various outdoor activities, including lake swimming, boat ramp, hiking, and fishing. We apologize for any inconvenience but we do not allow animals.

4.95 out of 5 average rating, 185 reviews

Flat in Danville

Main St, near dtwn casino, coffee, wifi, free park

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.

4.98 out of 5 average rating, 254 reviews

Fun Lake Getaway with Breathtaking Views

Fantastic getaway on beautiful Smith Mountain Lake! Enjoy stunning views on two sides of this top-floor, corner condo with a wrap-around deck and natural shade. It is perfect for a relaxing break or an adventure! Activities include boating (with guest docks), swimming (indoor and outdoor), pickle ball, working out, and relaxing in the hot tub, steam room or sauna! If you are working remotely, this quiet space includes a desk and high-speed wireless. The individual HVAC unit also has a UV light.

4.97 out of 5 average rating, 210 reviews

Home in Sandy Level

Antler Ridge Lodge

Only 3 miles from SMITH MOUNTAIN! Zip Code 24161. (There's another Sandy Level near NC.) It is well-stocked and waiting for your next get-a-way! Even have Gas Logs in the fireplace! Explore acres of yard, woods & creek. Leesville & SML beaches & boat launches are 9-30 mi away. Walk or ride 1/2-mi to the road's end at Leesville Lake. Horses/hikers/bikers are welcome along the 5-mi ridge of Smith Mt minutes away. Relax around a fire enjoying the starry sky or kick back in the comfortable lodge.

4.97 out of 5 average rating, 74 reviews

Cabin in Chatham

Log Cabin Retreat/Pet Friendly: Lake, Golf & Wine

WELCOME to this rustic log cabin nestled on a picturesque 80-acres! Enjoy the tranquility of nature while being just minutes from: -- ODAC/Olde Dominion Agricultural Complex (4 mi) -- Smith Mountain Lake (17 mi) -- Bridgewater Plaza (35 mi) -- Cedars Country Club (1 mi) -- Homeplace Vineyard (5.4 mi) -- Caesar's Casino (28 mi) This spacious cabin offers 2 bedrooms, 2 beds, 1 bath making it the perfect getaway for relaxation and adventure. BOOK NOW for an unforgettable stay!

5 out of 5 average rating, 27 reviews

Flat in Hurt

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.

4.9 out of 5 average rating, 248 reviews

Dock Holiday at Bernard's Landing

Experience the water and mountain views at spectacular this 1 bedroom, 1 bath top floor corner condo in desirable Dockside section of Bernard's Landing. Guests enjoy all the amenities of Bernard's Landing including 2 outdoor and 1 indoor pool, Basketball, tennis and pickle ball courts,beach area, restaurant, fitness center and marina area with boat rentals. All pools and beach are short walk from the front door. Enjoy stunning views from the walk-out deck in this well-stocked condo.

4.95 out of 5 average rating, 134 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!"

4.91 out of 5 average rating, 191 reviews

Lake Escape - Smith Mountain Lake Condo

Located in Bernard's Landing, SML, this ground-floor condo offers everything you need for a quick getaway or a week-long vacation. The condo has recently been re-decorated and offers beautiful lake views, convenient access to boat rentals, one of the best restaurants on SML (Napoli by the Lake), and all the amenities you need. Guests have access to indoor and outdoor pools (outdoor pools open seasonally), sandy beach area, sauna, gym, and tennis and pickle ball courts.

4.95 out of 5 average rating, 141 reviews

Bernard's Landing Bliss! Breathtaking Views

Come savor the breathtaking lake and mountain views and experience the best of Bernards Landing in this condo! Enjoy the best amenities - high end stainless appliances, big flat screen TVs, keypad door access – and the list goes on! River Rock Tiled Shower and Silestone Counters! Bernard’s Landing offers so much – 2 outdoor/1 indoor pool, hot tub, beach, gym, sauna, boat launch, courtesy dock, tennis, pickle ball, racquetball courts, The Landing Restaurant, and more!

4.97 out of 5 average rating, 107 reviews

Farm stay in Hurt

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!

4.95 out of 5 average rating, 188 reviews

Home in Pittsville

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.

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Popular amenities for Pittsylvania County holiday rentals

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Free parking on premises

Air conditioning

Other great holiday rentals in Pittsylvania County

5 out of 5 average rating, 28 reviews

Cozy Danville Retreat

ChrisRating, 5 stars3 days ago

This is a beautiful property, and I highly recommend!

4.98 out of 5 average rating, 44 reviews

Apartment in Huddleston

NEW, CLEAN - Belle's Boat Haven in SML

BrandyRating, 5 stars1 week ago

Loved our stay at SML! The coffee bar was a great touch and the towels were incredibly soft. Danielle and Ryan are great host. Would definitely come back!

4.8 out of 5 average rating, 85 reviews

Home in Moneta

Cabana Too at Smith Mountain Lake

AllisonRating, 5 stars5 days ago

Loved the location wonderful place to stay definitely want to return

4.97 out of 5 average rating, 32 reviews

Relaxing oasis

Alisha Rating, 5 stars2 days ago

Nice neighborhood, friendly neighbors, home was spotless, close to everything we were in town for!

5 out of 5 average rating, 43 reviews

The “Cedarbrook Retreat”

EricaRating, 5 stars1 week ago

Wow! This place was just as it was described! We thoroughly enjoyed everything! It was close to the casino restaurants and my favorite TJ Maxx!!!! Thanks again for the kindness that was shown annnnd the icing on the cake were the treats left by Noah!!! It made the overnight stay amazing!!

5 out of 5 average rating, 3 reviews

The Owl House

JerridRating, 5 stars3 weeks ago

Very quiet little neighborhood, but not too far away from the local restaurants. Plenty of space in the home. The enclosed back porch is a very nice seating area for a relaxing evening.

5 out of 5 average rating, 15 reviews

Home in Penhook

Cozy Lakeside Mountain Home

ChristopherRating, 5 stars5 days ago

this is a must stay if yoy want to relax from the outside world private dock was ver convienent and his house was very cozy this will be a destination i will come to again for sure !