Holiday rentals in Cumberland County

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Top-rated holiday rentals in Cumberland County

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Top guest favourite
An aerial view captures a spacious rural landscape featuring a cozy guest house bordered by expansive green fields and trees. A pond is visible nearby, along with cultivated areas. The distant hills create a serene backdrop, emphasizing the tranquility of this working farm.
Guest house in Dillwyn
4.94 out of 5 average rating, 78 reviews

Cozy Farm Cottage near Farmville Virginia

Our cozy guest house is situated on a 36 acre working farm where you will enjoy privacy and pastoral views. Our posted rate is for 2 guests. The town of Farmville is an easy drive 10 miles south of us, where you will find Longwood University, Hampden-Sydney College, Green Front Furniture, the High Bridge Trail, and activities on the Appomattox River. Charlottesville, Richmond and Lynchburg are less than an hour away. Cottage has one bedroom with two twin beds, and one bedroom with a double bed.

Top guest favourite
A comfortable house is situated on a spacious grassy lawn, surrounded by trees. A long gravel driveway leads to the home and a storage shed, while scattered clouds float in a clear blue sky above.
Home in Farmville
5 out of 5 average rating, 114 reviews

The Hide-A-Way

Follow a long gravel driveway before you can view this comfortable house in the country. This house is 12 easy miles from the Town of Farmville and all it has to offer. Longwood University and Hampden-Sydney College is near by. Visit High Bridge State Park for hiking and Greenfront is a shopping destination. Lots of dining options will appeal to every taste and plenty of other activities to enjoy in this area. There is no phone-internet or satellite at The Hide-A-Way, Cell phones do work.

Superhost
A two-story barndominium is set amidst lush greenery, showcasing a welcoming exterior with wooden accents. An inviting porch features several rustic chairs, framed by stone columns. Large windows are accentuated by wooden shutters, reflecting the natural beauty of the surrounding landscape.
Home in Cumberland
5 out of 5 average rating, 4 reviews

Happy Hollow - Barndo Retreat

Welcome to your home away from home! Experience the charm and comfort of this beautifully customized barndominium, the Happy Hallow. This spacious retreat offers over 2400 sq ft of inviting living space, featuring a relaxing steam shower, sliding barn doors, 4 cozy outdoor patios, cathedral ceilings, and a welcoming eat-in kitchen. Immerse yourself in the tranquility of country living in this luxurious 3-bedroom, 3-bath home, surrounded by the peaceful beauty of rolling hills and nature.

Guest favourite
The exterior of a modern barndominium is showcased, featuring a dark wood facade with contrasting wooden shutters. A spacious porch is supported by wooden beams, with two seating areas visible. A gravel drive leads to the entrance, surrounded by trees and natural landscaping.
Home in Cumberland
5 out of 5 average rating, 10 reviews

Barndominium River Retreat

Experience a river retreat at our luxury barndominium in Central Virginia! We are nestled in the heart of our 40 acres parcel with 2 acres of river front access where you can swim, fish or kayak. We are in the middle of Cumberland State Forest. Take a short 10 minute drive to Bear Creek Lake State Park for swimming, hiking, and boating. Our spacious home features 3 bedrooms, 3 full baths, a steam shower, and soaking tub. Relax in a hammock or enjoy hanging with friends by the camp fire

Guest favourite
The exterior of the hobbit house features a large, round green door framed by two circular windows. The structure is set into a grassy hill, surrounded by trees, with a soft sunlight illuminating the scene. A small garden area is visible near the entrance.
Campsite in Arvonia
4.96 out of 5 average rating, 70 reviews

Shireton: Cozy Off-Grid Cabin in Virginia’s Nature

Experience the charm of Shireton, a distinctive off-grid retreat tucked away in Virginia’s countryside. This cozy, handcrafted home features solar power, a relaxing copper soaking tub, and nearby hiking trails for outdoor adventure. A refundable security deposit of $200 applies. Disconnect from the world with no TV or Wi-Fi and reconnect with nature in a peaceful, rustic setting. Ideal for those looking to camp or explore local attractions. Book now for a serene experience!

Guest favourite
A vintage boxcar is displayed with its exterior painted in a light color featuring the words 'Linking North and South' with a stylized map of Virginia. A set of stairs leads to the entry, surrounded by greenery and natural wooden ground.
Train in Columbia
5 out of 5 average rating, 20 reviews

Boxcar with floor to ceiling glass doors

Guests staying in the Boxcar have access to the shared amenities of Rassawek Station including the patio “Flat Car” and our Lodge Cabin. Guests also have access to our ponds and 5+ miles of private country roads for hiking, running and biking. The boxcar living area has a sofa and coffee table and small area with table, two chairs and a mini fridge/freezer with a Keurig. The bedroom has a queen bed and dresser and there is a full bathroom with shower, sink and toilet.

Guest favourite
Home in Columbia
4.95 out of 5 average rating, 80 reviews

Riverview Cabin on the James

VERY secluded with PRIVATE River access, STUNNING views, and a Hot Tub! A unique property offers modern amenities with a cabin feel. Granite countertops and upgraded appliances, custom tile showers, high quality mattresses, leather reclining couch. But the best part is the covered porch overlooking the James River! With your own private river access, you can enjoy a cool dip in the water or just the serenity of the peace and quiet. Lots of wildlife and stunning views.

Superhost
A two-story Federal style brick home features a welcoming red door framed by white trim. The front yard is landscaped with vibrant pink flowering shrubs and well-maintained grass, creating a charming entrance under a bright blue sky.
Home in Farmville
4.72 out of 5 average rating, 47 reviews

Charming Home Near Longwood & Hampden-Sydney

Welcome to our charming two-story Federal style brick home in the heart of Farmville. This thoughtfully updated space features three private bedrooms with queen beds and one and a half bathrooms, offering comfort and room to unwind. Enjoy an easy walk to downtown shops, restaurants, and cafes, with Longwood University and campus events just minutes away. Ideal for weekend visits or extended stays, with weekly and monthly discounts available.

Top guest favourite
Home in Farmville
4.95 out of 5 average rating, 155 reviews

The Lake House

Enjoy nature in this lakefront 3 bed/1.5 bath retreat. This house is set off the road in a very serene and rural area, yet you are only a short drive away from many conveniences. Less than 5 miles from Downtown Farmville, restaurants, GreenFront, and Longwood University. About a 20 min to Hampden Sydney. This is the perfect place to disconnect from the outside world and relax dockside. *Please read all details below*

Top guest favourite
Home in Dillwyn
4.99 out of 5 average rating, 86 reviews

Vinca House

Designed to be a comfortable place to rest...or work. Easily accessible on State Route but set in a wooded lot in southern Buckingham County, fifteen minutes from Farmville and ten minutes from Dillwyn. Broadband internet for work or recreation. Sit outside and see the neighboring farm animals or the occasional wildlife activity. Our posted rate is for up to 2 guests.

Top guest favourite
A spacious backyard features a well-manicured lawn surrounded by large trees and two distinct buildings. The gray house, featuring a porch, is complemented by a vibrant red structure, both capturing a serene outdoor setting.
Guest house in Cumberland
4.97 out of 5 average rating, 124 reviews

Lucid Dreams little house

Have fun at Lucid Dreams Little house on the farm. You can go dream walking and feel so free and peaceful. Open land and woods. A place you just don’t want to leave. Rocky the Mimi horse will greet you in the yard. Redneck beach in the back where picnics are always fun. Check out our beautiful sun rises and sunsets. Bring your horse or a friend.

Top guest favourite
A charming carriage house showcases a light-colored exterior with extensive wraparound porches. Lush green grass and neatly arranged flower beds enhance the landscape. A stone chimney rises from the side, framed by tranquil trees and a clear blue sky.
Home in Farmville
5 out of 5 average rating, 25 reviews

Carriage House

Welcome to town and country! Relax in this calm, private carriage house while visiting Farmville. This equestrian styled home is located by a 42 acre horse farm, and one mile from High Bridge Trail state park! It is 3 miles from charming downtown and Longwood University. Only 8 miles from Hampden-Sydney College.

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