Holiday rentals in Chatham

4.96 out of 5 average rating, 80 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.

5 out of 5 average rating, 68 reviews

Home in Gretna

Little Haven Cottage

Leave the demands of life and enter the peace of our Little Haven Cottage. Enter our rendition of an English cottage and enjoy watching local wildlife pass through the tranquility. Your stay will offer a repose and the ability to connect through a slow and quiet experience. Surrounded by the growing Amish community and stores where you can buy Amish food/goods. 45 min to Liberty University/ Lynchburg 40 min to Smith Mountain Lake Under 20 min to historic railroad towns Gretna/Chatham/Altavista

4.97 out of 5 average rating, 209 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, 71 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, 245 reviews

Apartment in Moneta

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.

4.9 out of 5 average rating, 190 reviews

Cabin in Brookneal

Rustic Cabin on a 350+ acre Camp

This charming rustic cabin is located at Hat Creek Camp, a 350+ acre camp with over 7 miles of hiking trails and two lakes. The cabin has three rooms, a bedroom, bathroom, and common space/kitchen. The kitchen includes a stove, fridge, blender, coffee maker, and microwave. The bedroom has a Queen bed, and the bathroom has a spacious shower. This cabin is small but very personable, around the camp it is affectionately known as The Pickle. Perfect for quiet getaways in the country.

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!"

4.98 out of 5 average rating, 59 reviews

Home in Gretna

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

4.97 out of 5 average rating, 104 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!

4.88 out of 5 average rating, 137 reviews

Cute Comfy House

Only 1 mile from the new Caesars casino - Welcome to the cute comfy house! This home has 2 bedrooms with a queen in each room. There is an additional single person foldout cot in the closet. Freshly remodeled from top to bottom and situated on an acre in a quiet and peaceful neighborhood minutes away from Main St., Averette University, downtown and the Riverwalk. Washer/Dryer in the basement

4.9 out of 5 average rating, 123 reviews

Farm stay in Union Hall

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.

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Other great holiday rentals in Chatham

4.92 out of 5 average rating, 13 reviews

Home in Gretna

Farmhouse in Gretna, Virginia

DillonRating, 5 stars1 month ago

Place has everything you will need to make yourself at home beds were comfy backyard was very Nice! If I’m back up here I will be checking with Andrew about this house!

5 out of 5 average rating, 13 reviews

Cabin in Martinsville

Energize Retreat Cabin #3

TanyaRating, 5 stars1 month ago

The place was absolutely beautiful and peaceful. Well maintained and very clean. Thank you for the beauty.

5 out of 5 average rating, 13 reviews

Home in Huddleston

Lake Haven - Hot Tub! Mountain Views!

MikeRating, 5 stars2 weeks ago

This lakefront spot was perfect for a laid-back weekend with my childhood friends. The house was clean, updated, and had plenty of space for all of us to hang out and relax. The private dock was a standout—we spent a ton of time by the water, just catching up and enjoying the quiet. The host made everything easy, from check-in to check-out. Whether we were grilling, enjoying the hot tub, or just kicking back on the deck, it was exactly the kind of getaway we needed. Would definitely come back.

4.97 out of 5 average rating, 29 reviews

Relaxing oasis

ChristinaRating, 5 stars2 weeks ago

"I recently had the pleasure of staying at Jarrod Airbnb, and I cannot recommend it highly enough! From the moment we arrived, we were greeted with warmth and hospitality. The space was spotlessly clean, beautifully decorated, and equipped with all the amenities we needed for a comfortable stay. The location was perfect, with easy access to local attractions, restaurants, and public transport. We truly felt at home! One of the highlights of our stay was [mention any specific feature, like a stunning view, a cozy fire pit, or a fantastic kitchen]. Overall, our experience was fantastic, and I would definitely stay here again on future visits. Thank you, [Host's Name], for making our trip so memorable!"

4.99 out of 5 average rating, 75 reviews

Flat in Bassett

The Porch at Fairystone

DonaldRating, 5 stars3 days ago

We had a great time and even extended our stay. Spencer's place is very comfortable with all the amenities of home. Excellent place convenient to town.

5 out of 5 average rating, 70 reviews

Heart of Danville Renovated Modern 3bd/2ba.

AlexisRating, 5 stars4 weeks ago

This location was perfect for our trip to VIR. It was close to stores and less than half an hour from the track. Adelaide was friendly and responded quickly. The house was beautiful, clean and very well decorated.

5 out of 5 average rating, 18 reviews

Cabin in Union Hall

The Chalet at BWJ

AveryRating, 5 stars4 days ago

This place is amazing, the chalet was very clean and had everything needed for a nice get away. It’s located in a beautiful area with lots of farm life and is extremely peaceful and secluded. The hot tub is located in a perfect spot to either watch stars or the sunrise. Overall it was an awesome experience and I’d recommend it to anyone wanting a relaxing getaway. The host Coy was friendly and respectful and he responded very quickly to all questions.