A tree-lined path with a clear blue sky.

Holiday Rentals in Cumberland County

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Our top choices for Cumberland County holiday rentals

A log cabin with a porch, a small deck, and a fire pit area.

1. Getaway Cabin | Hot tub + Fire Pit + Trail Access

Getaway Cabin | Hot tub + Fire Pit + Trail Access
Farmville
9.8 out of 10, Exceptional, (74 reviews)
"I give this cabin a five-star rating! It was incredibly cozy, spotless, and made me feel right at home. Communication with the owner was excellent—they were friendly, responsive, and very accommodating throughout my stay. I highly recommend this cabin to anyone looking for a relaxing getaway. I would definitely stay here again!"
United States
Michelle R.
The price is €293
includes taxes & fees
19 Oct - 20 Oct
Getaway Cabin | Hot tub + Fire Pit + Trail Access
A log cabin interior with a fireplace, a television mounted on the wall, and a dining area.

2. Cedar Ridge Cabin | Hot Tub + Fire + Trail Access

Cedar Ridge Cabin | Hot Tub + Fire + Trail Access
Farmville
10.0 out of 10, Exceptional, (66 reviews)
"Second time we have stayed at this property and it is excellent! Very convenient to town also"
United States
Brandi P.
The price is €414
includes taxes & fees
14 Oct - 15 Oct
Cedar Ridge Cabin | Hot Tub + Fire + Trail Access
A two-story house with a deck, a front door, and a mailbox.

3. Trailside Cottage | Spacious 2BR Near Greenfront

Trailside Cottage | Spacious 2BR Near Greenfront
Farmville
10.0 out of 10, Exceptional, (1 review)
"This adorable 2 bedroom cottage was perfect for a weekend visit to FarmVille with another couple. Each bedroom has its own bathroom. Beds were comfortable. A short walk to the High Bridge Trail that can also take you right into town. It is also a short drive to Main St"
United States
Steven C.
The price is €250
includes taxes & fees
13 Oct - 14 Oct
Trailside Cottage | Spacious 2BR Near Greenfront
A modern kitchen with grey cabinets, stainless steel appliances, a window with blinds, and a painting on the wall.

4. Trailside 2BR Cottage | Walk Downtown + Greenfront

Trailside 2BR Cottage | Walk Downtown + Greenfront
Farmville
The price is €241
includes taxes & fees
13 Oct - 14 Oct
Trailside 2BR Cottage | Walk Downtown + Greenfront
A red cabin with a wooden deck and a metal roof, elevated on stilts, surrounded by trees.

5. Trailside Cottage | 1BR Near Greenfront

Trailside Cottage | 1BR Near Greenfront
Farmville
The price is €247
includes taxes & fees
13 Oct - 14 Oct
Trailside Cottage | 1BR Near Greenfront
A modern kitchen with stainless steel appliances, a central island, and a dining area with a view.

6. Cozy Trailside 1BR | Walk to Green Front

Cozy Trailside 1BR | Walk to Green Front
Farmville
The price is €292
includes taxes & fees
18 Oct - 19 Oct
Cozy Trailside 1BR | Walk to Green Front
A house with a covered porch, outdoor seating, and a well-lit deck area.

7. Steel Magnolias Cozy Main Home in Amelia County

Steel Magnolias Cozy Main Home in Amelia County
Amelia Court House
9.6 out of 10, Exceptional, (15 reviews)
"I would highly recommend Jenny’s VRBO- the house was beautiful, clean, and she was incredibly welcoming and communicative! "
United States
Marissa H.
The price is €272
includes taxes & fees
15 Oct - 16 Oct
Steel Magnolias Cozy Main Home in Amelia County
A brick house with a chimney, a front porch, and a mailbox.

8. Walk to Longwood • Sleeps 6 • Cozy Cottage Near Hampden-Sydney

Walk to Longwood • Sleeps 6 • Cozy Cottage Near Hampden-Sydney
Farmville
10.0 out of 10, Exceptional, (17 reviews)
"The house is a charming older home. Great location, very clean, would stay here again!"
United States
Tracy F.
The price is €322
includes taxes & fees
3 Nov - 4 Nov
Walk to Longwood • Sleeps 6 • Cozy Cottage Near Hampden-Sydney
A kitchen with a wooden ceiling, a bar area with stools, and a sign that says 'Handmade.'

9. Historic Powhatan Retreat | Walk to Restaurants & Distillery

Historic Powhatan Retreat | Walk to Restaurants & Distillery
Powhatan
10.0 out of 10, Exceptional, (6 reviews)
"The layout was comfortable, house was charming. Owner was very good with communication, and helpful with any questions that arose. Would definitely stay here again!"
United States
Ryan S.
The price is €241
includes taxes & fees
2 Nov - 3 Nov
Historic Powhatan Retreat | Walk to Restaurants & Distillery
A two-story house with a front porch, a central entrance, and a symmetrical window arrangement.

10. Private Guest Suite by Wineries/Orchards/Cville

Private Guest Suite by Wineries/Orchards/Cville
Palmyra
10.0 out of 10, Exceptional, (54 reviews)
"Very nice room and suite clean and accomdating "
United States
Nick S.
The price is €213
includes taxes & fees
13 Oct - 14 Oct
Private Guest Suite by Wineries/Orchards/Cville
A wooden hot tub with a stone fireplace in the background.

11. One of kind wellness/glamping experience right outside of Richmond with everything you need and more to truly relax.

One of kind wellness/glamping experience right outside of Richmond with everything you need and more to truly relax.
Mineral
10.0 out of 10, Exceptional, (7 reviews)
"Went here for our anniversary and it was an absolutely lovely time! Will definitely be back!"
United States
ValarieR
The price is €411
includes taxes & fees
14 Oct - 15 Oct
One of kind wellness/glamping experience right outside of Richmond with everything you need and more to truly relax.
A cozy living room with a brick fireplace, a flat-screen TV mounted above it, and a dining area with a wooden table and chairs.

12. Cozy Cabin w/ Hot Tub | State Park | Near Lake

Cozy Cabin w/ Hot Tub | State Park | Near Lake
Appomattox
9.8 out of 10, Exceptional, (34 reviews)
"Great location and had everything needed for a great stay. "
United States
Jeff S.
The price is €259
includes taxes & fees
19 Oct - 20 Oct
Cozy Cabin w/ Hot Tub | State Park | Near Lake
A modern kitchen with a large island, a built-in oven, and a window with curtains.

13. Bluebird Cottage B: Quiet, Firepit, Patio, Games

Bluebird Cottage B: Quiet, Firepit, Patio, Games
Palmyra
10.0 out of 10, Exceptional, (63 reviews)
"The host was very responsive and we thoroughly enjoyed staying there. Beautiful backyard!"
United States
Kelli c.
The price is €233
includes taxes & fees
11 Nov - 12 Nov
Bluebird Cottage B: Quiet, Firepit, Patio, Games
A covered porch with two wooden rocking chairs and a view of a wooded area with autumn foliage.

14. Still Waters a secluded quiet lake front home close to Hampden Sydney & Longwood

Still Waters a secluded quiet lake front home close to Hampden Sydney & Longwood
Pamplin
10.0 out of 10, Exceptional, (9 reviews)
"We loved the beauty of the home; the location was quiet and restful. It was very easy to communicate with Renee. For our family it was a perfect location to vacation. "
United States
David W.
The price is €332
includes taxes & fees
13 Oct - 14 Oct
Still Waters a secluded quiet lake front home close to Hampden Sydney & Longwood
A compact kitchen with a stove, oven, coffee maker, and a refrigerator.

15. Pine Grove Apartment: Visit Monticello, wineries, UVA

Pine Grove Apartment: Visit Monticello, wineries, UVA
Troy
9.4 out of 10, Exceptional, (6 reviews)
"Was a great place to lay our heads for the night while we were in town for a wedding very cozy and had everything you could need would highly recommend!"
United States
Jordan
The price is €224
includes taxes & fees
13 Oct - 14 Oct
Pine Grove Apartment: Visit Monticello, wineries, UVA
A single-story house with a front porch and a covered driveway.

16. The Country Retreat – Cozy Comfort Meets Peaceful Countryside

The Country Retreat – Cozy Comfort Meets Peaceful Countryside
Scottsville
9.4 out of 10, Exceptional, (6 reviews)
"Nice clean place out in the country. We were there for Memorial Day weekend and had a nice relaxing time."
United States
Michael L.
The price is €311
includes taxes & fees
20 Oct - 21 Oct
The Country Retreat – Cozy Comfort Meets Peaceful Countryside
A wooden deck with wicker chairs and a table, surrounded by a wooden railing and greenery.

17. Visit Monticello, Wineries, UVA: Room for a Crowd

Visit Monticello, Wineries, UVA: Room for a Crowd
Troy
9.4 out of 10, Exceptional, (24 reviews)
"Great place for us, comfortable and well-equipped."
United States
Lynn F.
The price is €665
includes taxes & fees
18 Oct - 19 Oct
Visit Monticello, Wineries, UVA: Room for a Crowd
A geodesic dome structure with a hot tub, seating area, and a small wooden building in a forest setting.

18. One of kind wellness/glamping experience with wellness amenities, covered outdoor dining, a complete live fire cooking setup, and a clear star gazing top.

One of kind wellness/glamping experience with wellness amenities, covered outdoor dining, a complete live fire cooking setup, and a clear star gazing top.
Mineral
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful location and close to Richmond. Everything was functional, spotless, and very easy to use from arrival to departure. Can't say enough about how great an experience this was and will definitely be returning in the future"
United States
AlexanderG
The price is €399
includes taxes & fees
13 Oct - 14 Oct
One of kind wellness/glamping experience with wellness amenities, covered outdoor dining, a complete live fire cooking setup, and a clear star gazing top.
Holiday Home Exterior [summer]

19. 2 Queen Bed| Non Smoking

2 Queen Bed| Non Smoking
Keyswille VA
10.0 out of 10, Exceptional, (160 reviews)
"Conveniently located next to key spots but not too noisy at night, really enjoyed that balance during our visit."
United States
Anonymous traveller
The price is €76
includes taxes & fees
11 Nov - 12 Nov
2 Queen Bed| Non Smoking
A modern kitchen with stainless steel appliances, a dining table with chairs, and a window with blinds.

20. Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries

Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
Troy
9.2 out of 10, Wonderful, (150 reviews)
"Had a great stay! Everything was as expected and the property was nice."
United States
Jules R.
The price is €191
includes taxes & fees
19 Oct - 20 Oct
Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cumberland County Hotel Reviews

Cedar Ridge Cabin | Hot Tub + Fire + Trail Access

Cedar Ridge Cabin | Hot Tub + Fire + Trail Access

10/10 Excellent
"Spectacular rental. Super cozy and very clean."
Melody R. 2-night trip
Posted 5 hours ago
Cedar Ridge Cabin | Hot Tub + Fire + Trail Access

Find out more about Cumberland County

Holiday Homes in Cumberland County

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