Book Holiday Homes in Cumberland

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Cumberland

Cozy retreat just 1 mile from the Fine Creek Brewery & eclectic wedding venue.

Cozy retreat just 1 mile from the Fine Creek Brewery & eclectic wedding venue.

Powhatan
With a stay at this vacation home in Powhatan, you'll be 19.5 mi (31.5 km) from Short Pump Town Center and 20.2 mi (32.5 km) from University of Richmond.
Cozy retreat just 1 mile from the Fine Creek Brewery & eclectic wedding venue.
Charming Virginia Retreat w/ Covered Porch & Yard!

Charming Virginia Retreat w/ Covered Porch & Yard!

Farmville
With a stay at this vacation home in Farmville, you'll be within a 10-minute drive of J Fergeson Gallery and Mainly Clay.
Charming Virginia Retreat w/ Covered Porch & Yard!
In the Village Of Powhatan- walking distance to owners restaurant

In the Village Of Powhatan- walking distance to owners restaurant

Powhatan
When you stay at this vacation home in Powhatan, you'll be 8 minutes by car from Mill Quarter Plantation Golf Club.
In the Village Of Powhatan- walking distance to owners restaurant
Save an average of 15% on thousands of hotels when you're signed in
Secluded Cabin w/ Hot Tub - State Park - Near Lake

Secluded Cabin w/ Hot Tub - State Park - Near Lake

Appomattox
Located in Appomattox, this vacation home is in the mountains, within a 15-minute drive of Appomattox River and Holliday Lake State Park.
Secluded Cabin w/ Hot Tub - State Park - Near Lake
5 Bedroom Hilltop Villa with Magnificent Views

5 Bedroom Hilltop Villa with Magnificent Views

Buckingham
When you stay at this vacation home in Buckingham, you'll be on a river and 14 minutes by foot from James River.
5 Bedroom Hilltop Villa with Magnificent Views
Cozy Get-A-Way in Neighborhood On 3 Lakes, With Fishing Docks, Firepit, Kayaks

Cozy Get-A-Way in Neighborhood On 3 Lakes, With Fishing Docks, Firepit, Kayaks

Powhatan
The price is AU$666 per night from 23 Apr to 24 Apr
AU$666
includes taxes & fees
23 Apr - 24 Apr
With a stay at this vacation home in Powhatan, you'll be 8.8 mi (14.2 km) from Windy Hill Sports and 9.6 mi (15.5 km) from Appomattox River.
Cozy Get-A-Way in Neighborhood On 3 Lakes, With Fishing Docks, Firepit, Kayaks
Riverview Cabin on the James

Riverview Cabin on the James

Cumberland County
The price is AU$469 per night from 9 Apr to 10 Apr
AU$469
includes taxes & fees
9 Apr - 10 Apr
This vacation home is 11.8 mi (19 km) from Byrd Cellars Winery and Vineyard and 12.2 mi (19.7 km) from Elk Island Winery.
Riverview Cabin on the James
Steel Magnolias Cozy Main Home in Amelia County

Steel Magnolias Cozy Main Home in Amelia County

Amelia Court House
The price is AU$461 per night from 14 Apr to 15 Apr
AU$461
includes taxes & fees
14 Apr - 15 Apr
Located in Amelia Court House, this vacation home is on a lake, within a 15-minute drive of Appomattox River and Amelia County Court House.
Steel Magnolias Cozy Main Home in Amelia County
106 acre Farm with Animals, River & Private Pond, near Wineries and Breweries

106 acre Farm with Animals, River & Private Pond, near Wineries and Breweries

Scottsville
When you stay at this vacation home in Scottsville, you'll be on the waterfront, within a 5-minute drive of James River and Dorrier Park.
106 acre Farm with Animals, River & Private Pond, near Wineries and Breweries
Don't see what you're looking for?
See all available properties in Cumberland
View all properties
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.

Cumberland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Cumberland vacation homes are the perfect way for you to wing it.

Holiday houses in Cumberland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Cumberland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Cumberland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Cumberland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Cumberland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Cumberland Holiday Homes essential information

Accommodation
16 Holiday Homes
Lowest Price
AU$115
Highest Price
AU$666
Popular accommodation
Cozy retreat just 1 mile from the Fine Creek Brewery & eclectic wedding venue. , Charming Virginia Retreat w/ Covered Porch & Yard!, In the Village Of Powhatan- walking distance to owners restaurant, Secluded Cabin w/ Hot Tub - State Park - Near Lake, 5 Bedroom Hilltop Villa with Magnificent Views, Cozy Get-A-Way in Neighborhood On 3 Lakes, With Fishing Docks, Firepit, Kayaks, Riverview Cabin on the James, Steel Magnolias Cozy Main Home in Amelia County, 106 acre Farm with Animals, River & Private Pond, near Wineries and Breweries

Top trending hotels in Cumberland

Hotel Weyanoke

Hotel Weyanoke

3.5 out of 5
202 High Street, Farmville, VA
Fully refundableReserve now, pay when you stay
The price is AU$178 per night from 20 Apr to 21 Apr
AU$178
includes taxes & fees
20 Apr - 21 Apr
Located in Farmville, Hotel Weyanoke is just steps from Longwood University and 4 minutes by foot from Longwood Center for the Visual Arts.
Hotel Weyanoke
Days Inn by Wyndham Farmville

Days Inn by Wyndham Farmville

2 out of 5
2015 South Main St., Farmville, VA
Fully refundableReserve now, pay when you stay
The price is AU$115 per night from 20 Apr to 21 Apr
AU$115
includes taxes & fees
20 Apr - 21 Apr
With a stay at Days Inn by Wyndham Farmville in Farmville, you'll be in the historical district, a 5-minute walk from Weyanoke Park and a 3-minute drive from ...
Days Inn by Wyndham Farmville
Tru by Hilton Farmville

Tru by Hilton Farmville

2.5 out of 5
1913 South Main Street, Farmville, VA
Fully refundableReserve now, pay when you stay
The price is AU$210 per night from 22 Apr to 23 Apr
AU$210
includes taxes & fees
22 Apr - 23 Apr
Located in Farmville, Tru by Hilton Farmville is in the historical district, within a 5-minute drive of Weyanoke Park and Robert Russa Moton Museum.
Tru by Hilton Farmville
Save an average of 15% on thousands of hotels when you're signed in
Holiday Inn Express & Suites Farmville by IHG

Holiday Inn Express & Suites Farmville by IHG

2.5 out of 5
404 Sunchase Blvd, Farmville, VA
Fully refundable
The price is AU$229 per night from 1 May to 2 May
AU$229
includes taxes & fees
1 May - 2 May
With a stay at Holiday Inn Express & Suites Farmville by IHG in Farmville, you'll be within a 5-minute drive of Longwood Golf Course and Longwood Center for ...
Holiday Inn Express & Suites Farmville by IHG
Don't see what you're looking for?
See all available properties in Cumberland
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.