Vacation rentals in Cumberland County

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Top-rated vacation rentals in Cumberland County

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Top guest favorite
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.
Guesthouse in Dillwyn
4.94 out of 5 average rating, 80 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.

Guest favorite
A spacious living area features a large stone fireplace as the focal point, surrounded by mounted animal heads. Cozy seating includes a sofa and an armchair with a decorative pattern. Soft lighting is provided by two floor lamps, creating a warm and inviting ambiance.
Vacation home in Columbia
4.95 out of 5 average rating, 44 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 favorite
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, 132 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.

Guest favorite
Cabin in Farmville
4.97 out of 5 average rating, 189 reviews

Cedar Ridge Lodge | Hot Tub + Fire + Trail Access

Gather your crew and escape to Cedar Ridge Lodge! A timber-frame log lodge tucked into 27 private wooded acres in Virginia, just 3 hrs from DC and 1 hr from Richmond. Spend your days biking/hiking High Bridge Trail, your evenings around the fire ring, and your nights soaking in the private hot tub on the wrap-around porch. Wood-burning fireplace, game loft with board games, full kitchen, and WiFi when you need it. Downtown Farmville is just minutes away. Come relax and unwind!

Guest favorite
Train in Columbia
5 out of 5 average rating, 21 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 favorite
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
4.94 out of 5 average rating, 88 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 favorite
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, 11 reviews

Private Riverfront Lodge on 40 Acres Pets Fire Pit

Escape to The Retreat at Timber Lodge, a peaceful 40-acre Virginia getaway with riverfront access, fire pit, porches, and room for the whole family. Perfect for family vacations, couples, book clubs, small retreats, wedding guests, and outdoor lovers. Enjoy Bear Creek Lake State Park nearby for swimming and hiking then come back to relax in comfort with 3 bedrooms, 3 full baths, a steam shower, soaking tub, full kitchen, Wi-Fi, and pet-friendly space.

Guest favorite
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, 156 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*

Guest favorite
Apartment in Dillwyn
5 out of 5 average rating, 8 reviews

Cozy Studio near Farmville in the countryside

Cozy studio apartment attached to The Eppes House. The Eppes House is available for rent under another listing. Nestled in the peaceful countryside of Dillwyn, VA, you're just 9 miles from Farmville, where you can explore local dining, charming shops, and the seasonal farmers market. Whether you're here to unwind in nature, sip local wine, or dive into Virginia’s rich history, this is the perfect base.

Guest favorite
Home in Farmville
5 out of 5 average rating, 8 reviews

Trailside Cottage | Spacious 2BR Near Greenfront

Stay at Trailside Cottages, a newly built 2-bedroom cottage in Farmville near the High Bridge Trail. Walk to Greenfront and downtown Farmville for shopping, dining, and entertainment, or drive downtown in just 3 minutes. With extra space, modern finishes, and a great location, it’s ideal for families, friends, or a relaxing getaway. ***More photos coming. Adding finishing touches!***

Top guest favorite
Home in Dillwyn
4.99 out of 5 average rating, 92 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 favorite
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.
Guesthouse in Cumberland
4.96 out of 5 average rating, 138 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 vacation rentals