A green barn with white trim, a wooden fence, and a large tree in the background.

Photo by Janet Sumner

Orange County holiday homes

We found 457 holiday rentals — enter your dates for availability

Select from 61 homes, 24 cottages and other holiday rentals in Orange County to find one that's perfect for your trip. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as Wi-Fi and a washer and dryer. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Popular Orange County destinations on Bookabach

A sunset over a calm lake with a silhouette of trees and a cloudy sky.

Gordonsville

A large brick building with a central portico and a surrounding lawn.

Orange

A rural landscape with a white fence, green fields, and a few buildings in the distance.

Barboursville

A historical reenactment with a cannon firing, surrounded by participants in period attire.

Locust Grove

A park with a lake, autumn trees, and a person walking.

Lake of the Woods

A white church with a tall tower and arched windows.

Rapidan

Holiday rentals with weekly discounts – Orange County

Showing deals for:8 Jan - 15 Jan

Exceptional

(149 reviews)

True tranquility at Lake Anna

Mineral

8% off

NZ$7,339

for 7 nights, 1 home

NZ$1,048 per night

includes taxes & fees

Peaceful forest retreat with glowing porch views at sunset

Cozy forest fire pit with rustic seating and a glowing retreat

Cozy modern living room with fireplace, TV, and bright outdoor views

Sunlit primary bedroom with forest views and stylish, cozy finishes

Wonderful

(5 reviews)

NEW 5BR Private Luxury Lake Anna Home

Spotsylvania Courthouse

15% off

NZ$7,105

for 7 nights, 1 home

NZ$1,015 per night

includes taxes & fees

Exceptional

(133 reviews)

Renovated lake front property on quiet cove with flat yard for outdoor fun

Mineral

7% off

NZ$6,101

for 7 nights, 1 home

NZ$872 per night

includes taxes & fees

Exceptional

(9 reviews)

River Rock Villa -Secluded Luxury Resort Retreat - 4,000 Acres & River Trails

Fredericksburg

8% off

NZ$17,271

for 7 nights, 1 home

NZ$2,467 per night

includes taxes & fees

Exceptional

(10 reviews)

The Farmhouse At Oak Creek Farm

Unionville

8% off

NZ$3,943

for 7 nights, 1 room

NZ$563 per night

includes taxes & fees

Exceptional

(8 reviews)

Welcome to your Blue water Escape! A cozy 3-bedroom home on Lake Anna waterfront

Mineral

8% off

NZ$6,910

for 7 nights, 1 home

NZ$987 per night

includes taxes & fees

Exceptional

(173 reviews)

The Natchez - quiet front porch & rockers.

Ruckersville

8% off

NZ$2,294

for 7 nights, 1 cabin

NZ$328 per night

includes taxes & fees

Exceptional

(64 reviews)

The Cabin at the Lake

Madison

8% off

NZ$2,748

for 7 nights, 1 cabin

NZ$393 per night

includes taxes & fees

Exceptional

(39 reviews)

Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.

Gordonsville

18% off

NZ$2,840

for 7 nights, 1 home

NZ$406 per night

includes taxes & fees

Exceptional

(10 reviews)

THE SERENE COTTAGE.

Fredericksburg

7% off

NZ$3,241

for 7 nights, 1 home

NZ$463 per night

includes taxes & fees

Exceptional

(9 reviews)

Country Retreat Near Shenandoah & Old Rag | Family Friendly Getaway

Madison

6% off

NZ$4,681

for 7 nights, 1 home

NZ$669 per night

includes taxes & fees

Exceptional

(10 reviews)

Tatum's Mtn View Retreat- SAUNA-Hiking- Unit A

Madison

8% off

NZ$2,449

for 7 nights, 1 home

NZ$350 per night

includes taxes & fees

Exceptional

(45 reviews)

Newly renovated entire guest suite in Orange County.

Orange

17% off

NZ$1,489

for 7 nights, 1 home

NZ$213 per night

includes taxes & fees

Exceptional

(8 reviews)

Mid-Century Modern Woodland Retreat with Hot Tub, Cold Water Plunge, & Fire Pit!

Culpeper

8% off

NZ$5,248

for 7 nights, 1 home

NZ$750 per night

includes taxes & fees

Dining Room (seats 10, Table in Kitchen seats 6)

Exceptional

(48 reviews)

1856 Manor House on 600-Acre Working Horse/Cattle Estate

Gordonsville

17% off

NZ$6,347

for 7 nights, 1 home

NZ$907 per night

includes taxes & fees

Exceptional

(11 reviews)

Relaxing cottage in the woods just minutes from wineries,hiking,restaurants.

Barboursville

12% off

NZ$2,994

for 7 nights, 1 cottage

NZ$428 per night

includes taxes & fees

Grand Room Couch - Converts to full bed - legs come out of the back, tilt down

Wonderful

(169 reviews)

6BR 225' Lakefront!!! Hot Tub, Dock, Private Boat Ramp, XFinity 400Mb wifi

Mineral

6% off

NZ$4,293

for 7 nights, 1 home

NZ$613 per night

includes taxes & fees

Mountain Views. The sun sets on the left side of this picture.

Exceptional

(143 reviews)

Servants' Cottage on 600 Acre Working Horse/Cattle Estate

Gordonsville

17% off

NZ$1,992

for 7 nights, 1 cottage

NZ$285 per night

includes taxes & fees

Exceptional

(106 reviews)

One of Central Virginia's most historic Private Guest Residences

Orange

6% off

NZ$4,011

for 7 nights, 1 home

NZ$573 per night

includes taxes & fees

Exceptional

(89 reviews)

'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.

Gordonsville

17% off

NZ$3,012

for 7 nights, 1 cottage

NZ$430 per night

includes taxes & fees

Exceptional

(24 reviews)

Charming 2-bedroom cottage in lovely Madison with WiFi, AC

Madison

8% off

NZ$2,685

for 7 nights, 1 cottage

NZ$384 per night

includes taxes & fees

Modern stainless appliances are surrounded by Taj Mahal countertops

You can count on homegrown, seasonal flower arrangements. We love our guests.

Exceptional

(34 reviews)

Classic Circa 1929 Estate by Montpelier, Wineries, Charlottesville, Pet Friendly

Somerset

8% off

NZ$5,466

for 7 nights, 1 home

NZ$781 per night

includes taxes & fees

Back view, covered deck and open air deck

Exceptional

(108 reviews)

Luxury Lakefront Living with the Comforts of Home

Locust Grove

8% off

NZ$7,837

for 7 nights, 1 home

NZ$1,120 per night

includes taxes & fees

Exceptional

(8 reviews)

Lake Anna • Lake Access • New Boat Dock • Fast WiFi • Small Dog Friendly

Mineral

6% off

NZ$2,616

for 7 nights, 1 home

NZ$374 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Chalet

Find the best place to stay - Orange County

Premier Host

Rustic Luxury Near Charlottesville/Montpelier/Wineries /A Historic Cabin Retreat

Sleeps 6 · 3 bedrooms · 2+ bathrooms

Premier Host

One of Central Virginia's most historic Private Guest Residences

Sleeps 6 · 2 bedrooms · 2 bathrooms

Stone Bridge Farm - 5BR Historic Riverfront Estate

Sleeps 12 · 5 bedrooms · 3+ bathrooms

Historic Manor House with Beautiful Pool and Mountain Views

Sleeps 12 · 4 bedrooms · 4 bathrooms

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Sleeps 2 · 1 bedroom

Premier Host

Lovers Lane FarmStay on a working family farm. Cows, sheep, bees, garden & more

Sleeps 4 · 1 bedroom · 1 bathroom

Find the perfect holiday rental for your Orange County getaway

Learn about the unique charm of Orange County with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Orange County

Are you hoping to discover attractions to see during your stay? Venture out of your cosy holiday rental and experience everything that Orange County has to offer. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

Barboursville Vineyards (10.8 mi / 17.4 km)
Early Mountain Vineyards (12.9 mi / 20.8 km)
Castle Hill Cider (14.6 mi / 23.5 km)
Keswick Vineyards and Winery (15 mi / 24.2 km)
Old House Vineyards (18.5 mi / 29.8 km)
Lake Anna Winery (20.7 mi / 33.3 km)

Exploring the natural features in Orange County

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Orange County is a great place to get out in nature. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

Shenandoah National Park (25.8 mi / 41.6 km)
Lake Anna State Park (17.6 mi / 28.3 km)
Lake Anna Marina (21.2 mi / 34.2 km)
Swift Run Gap Entrance Shenandoah (24.8 mi / 39.9 km)
Lake Anna (25.3 mi / 40.7 km)
Carter Mountain Orchard (26.4 mi / 42.4 km)

Frequently asked questions

What is the best area to stay in Orange County when booking a holiday home?

If you're thinking about a trip to Orange County, Locust Grove is one of the most desired places to stay. Whether you choose a cabin, condo or another property type, you'll always have the entire place to yourself.

What is the most popular type of holiday home accommodation in Orange County?

According to our research, houses are the most desirable type of holiday home in Orange County. But that goes without saying, everyone's idea of the perfect trip will differ. Bookabach has holiday homes with every size, shape and budget in mind, so you're bound to find the perfect match.

How much does it cost to rent a holiday home in Orange County?

A range of things influence the price of a holiday home in Orange County, such as the length of stay, type of property and season. However, all Bookabach homes have something in common — excellent value. Just add your travel dates to find your ideal match.

How much does it cost to rent a beach house in Orange County?

The average price for a holiday home by the beach in Orange County will depend on when you'll be there and the size and type of property you're looking for. You can find prices quickly and easily on Bookabach by entering your dates of travel. Then make use of the filter tool to choose the number of bedrooms and amenities important to you, like air conditioning, WiFi and a pool.

What are popular home amenities in Orange County?

When it comes to home amenities that people are on the lookout for in Orange County, a fridge, a microwave oven and off-street parking options are the most popular. With Bookabach holiday homes, there are options to fit your style and taste, whether you're going on a holiday with your partner, your family or even pets.

Are there large group holiday homes in Orange County?

You can pick from 12 properties in Orange County that can host a group of 10 or more guests. Whether you're organising a trip with the family or an event like a birthday party, there's ample room to get your loved ones together under the same roof.

What are the top attractions for families in Orange County?

There are lots of fun things to see and do with the family in Orange County, such as:

St. Thomas Episcopal Church
James Madisons Montpelier
Ellwood Manor

Can I find two-bedroom holiday homes in Orange County?

Orange County has 11 two-bedroom holiday homes to select from. Discover a holiday home with all the privacy and space you're looking for at an attractive price on Bookabach.

Are there holiday homes with WiFi in Orange County?

Whether you want to keep up with the latest news, look over emails or surf your social networks, there are 27 holiday homes with WiFi in Orange County. Check the "WiFi" box when searching on Bookabach and stay connected on your holiday.

How old do you have to be to rent a holiday home in Orange County?

You'll need to check with the Orange County holiday home you're considering on Bookabach as the age limit differs. However, normally it's 16, 18 or 21.

How long can I rent a holiday home in Orange County for?

The length of time you can book a holiday home in Orange County is up to the property. Simply enter your chosen dates to display a list of options offering extended stays. With plenty of creature comforts like washing machines and kitchens, as well as some offering weekly or monthly discounts, you're sure to get the perfect place to call your home away from home in Orange County.

More holiday ideas

Holiday Rentals