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
4.93 out of 5 average rating, 75 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.

Superhost
The cabin is situated on a gently sloping landscape, surrounded by greenery. Its exterior features light grey siding and large windows, complemented by a screened porch. Steps lead up to the entrance, while trees provide a natural backdrop enhancing the serene setting.
Home in Farmville
5 out of 5 average rating, 4 reviews

Farmville Main Lake House

Welcome to our rustic yet cozy cabin overlooking Farmville Lake. This peaceful retreat is minutes from Longwood and Hampden-Sydney. The home has plenty of room with 4 bedrooms and 2 baths. This tranquil property is perfect for taking a walk or reading a book on the screened porch with beautiful lake views. Beds include 1 king, 2 queens, 1 double, 1 twin. Towels included. *Renters must be at least 30 years old. **Additional 1 room guest house located on the property also available for rent.

Guest favourite
The exterior of a green, converted train car is shown, featuring large windows and a set of steps leading to a black railing. Surrounding vegetation provides a natural backdrop, enhancing the serene setting along the railway.
Train in Columbia
4.98 out of 5 average rating, 56 reviews

Pullman Train Car at Rassawek

Our Pullman Car is one of 3 converted train cars available for rentals. The car was built by Pullman Co. in 1888. Guests staying in this car have access to the shared amenities of Rassawek Station including the patio “Flat Car” and our Lodge Cabin. Guests can also use the ponds on the property as well as the 5+ miles of private country roads for hiking, running and biking. The converted car has a living area, full kitchen, a bedroom with two double beds, a full bath with shower and a half bath.

Guest favourite
A cozy living area features a large stone fireplace, adorned with mounted animal heads, including a moose and bears. Comfortable seating is provided by a plush sofa and armchairs, while artwork and warm lighting create a relaxed atmosphere. A rug adds warmth underfoot.
Holiday home in Columbia
4.95 out of 5 average rating, 39 reviews

Absolute heaven for outdoor enthusiasts!

If you love the outdoors and seclusion, Hooper's Rock Farm is for you. 1.5 miles of James River frontage in Cumberland Co, VA, 30-acre private lake, and 650 acres of fields, woods, and hills to explore and hike. Two living areas - one with large stone fireplace. Full kitchen. Screened porch overlooking lake. Sat TV. 2 John boats with trolling motors available for bass and crappie fishing in the lake. Entrance is 1 mile from public boat landing for James River access. Near many VA vineyards.

Top guest favourite
A gravel driveway leads toward a scenic countryside view, framed by trees on either side. At the entrance, two large tree stumps stand prominently, while a mailbox and a signpost indicate the property location. A soft sunset glow is visible in the distance.
Home in Farmville
5 out of 5 average rating, 99 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, 3 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, 9 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
A hobbit house structure features a large, rounded door surrounded by a circular frame. The grass-covered roof blends with the natural landscape, with soft, green mounds and stepping stones leading to the entrance. Trees stand tall in the background, providing a serene forest setting.
Campsite in Arvonia
4.94 out of 5 average rating, 54 reviews

Shireton

Welcome to our hobbit house! As the property is off the grid, our solar panels may be unreliable at times. To ensure your comfort, we’ve installed a quiet backup generator that activates easily if power is interrupted. Set in a remote, natural location, we encourage guests to embrace the “glamping” atmosphere. Please note, we do not offer discounts for generator use. If this sounds like your ideal getaway, please read the full description and reach out w/ any questions.

Guest favourite
A calm river scene features smooth, dark rocks at the water's edge, with gentle ripples reflecting the clear blue sky. Lush green trees line the riverbanks, enhancing the serene atmosphere. The landscape suggests a secluded natural environment perfect for relaxation.
Home in Columbia
4.96 out of 5 average rating, 69 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.

Guest favourite
A serene lakefront view showcases a spacious green lawn leading to a small pavilion. The pavilion features a covered area for relaxation, with a clear view of the tranquil lake surrounded by trees under a blue sky with scattered clouds.
Home in Farmville
4.95 out of 5 average rating, 151 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
A brand-new one-story house features a light yellow exterior with white trim and a metal roof. The entrance is accentuated by a small staircase leading to the front door, framed by large windows. Surrounding the home are well-maintained shrubs and a gravel driveway.
Home in Dillwyn
4.99 out of 5 average rating, 78 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, 106 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.

Popular amenities for Cumberland County holiday rentals