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

Holiday Rentals in Orange County

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Our top choices for Orange County holiday rentals

A garden pathway with various plants and a statue.

1. The Blenheim Suite in historic Holladay House

The Blenheim Suite in historic Holladay House
Orange
10.0 out of 10, Exceptional, (5 reviews)
"Had a weekend visit and location worked very well. Enjoyed my visit."
United States
Merrie Mac S.
The Blenheim Suite in historic Holladay House
A grassy field with a wooden fence, trees, and a distant building.

2. Servants' Cottage on 600 Acre Working Horse/Cattle Estate

Servants' Cottage on 600 Acre Working Horse/Cattle Estate
Gordonsville
9.8 out of 10, Exceptional, (143 reviews)
"The cottage had everything you need."
United States
William J.
The price is €185
includes taxes & fees
20 Oct - 21 Oct
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
Two people sitting at a wooden table outdoors, holding glasses of a beverage.

3. Elegant Cottage on 600 Acre Horse & Livestock Farm

Elegant Cottage on 600 Acre Horse & Livestock Farm
Gordonsville
9.8 out of 10, Exceptional, (158 reviews)
"Great secluded property on a beautiful setting. "
United States
Todd R.
Elegant Cottage on 600 Acre Horse & Livestock Farm
A house with a brick chimney, a small window, and a wooden deck.

4. Newly renovated entire guest suite in Orange County.

Newly renovated entire guest suite in Orange County.
Orange
9.8 out of 10, Exceptional, (45 reviews)
"The stay was great. Very close to all the nearby attractions and 30 minutes to skyline drive"
United States
vishal k.
Newly renovated entire guest suite in Orange County.
A living room with a fireplace, a chandelier, and a sofa.

5. The Pembroke Room in the historic Holladay House

The Pembroke Room in the historic Holladay House
Orange
9.4 out of 10, Exceptional, (3 reviews)
"The property is in the perfect location for a visit to Montpelier! Great restaurants and events are nearby. Very cozy! Great host! Expect what you would expect from a historic home. We will return."
United States
Robert
The Pembroke Room in the historic Holladay House
A modern kitchen with dark cabinets, stainless steel appliances, and a wooden dining table.

6. Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.

Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
Gordonsville
9.8 out of 10, Exceptional, (46 reviews)
"Beautiful property and family friendly."
United States
Tracy
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
A wooden cabin with a deck, surrounded by a grassy area and a flowering tree.

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

'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.
Gordonsville
9.8 out of 10, Exceptional, (89 reviews)
"Location stood out.4th time at the Pond House."
United States
Jeff C.
The price is €276
includes taxes & fees
20 Oct - 21 Oct
'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.
A living room with a stone fireplace, black leather sofa, and a flat-screen TV mounted on the wall.

8. Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm

Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
Gordonsville
9.6 out of 10, Exceptional, (35 reviews)
"The home was great, lots of space and sleeping areas. The farm itself was amazing. Would definitely stay again. Having a golf cart was a so fun."
United States
B S.
Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
A grassy field with three wooden Adirondack chairs and a wooden table.

9. Pre-Civil War Servants' Cottage on Huge Horse and Cattle Farm near Charlottesville, Virginia

Pre-Civil War Servants' Cottage on Huge Horse and Cattle Farm near Charlottesville, Virginia
Gordonsville
Pre-Civil War Servants' Cottage on Huge Horse and Cattle Farm near Charlottesville, Virginia
A living room with a stone fireplace, black leather sofa, and a flat-screen TV.

10. Spacious Modular Rental on Huge Horse and Cattle Farm near Charlottesville, Virginia

Spacious Modular Rental on Huge Horse and Cattle Farm near Charlottesville, Virginia
Gordonsville
10.0 out of 10, Exceptional, (1 review)
"Very homey spacious place. The horses loved to say hi!"
United States
Stephen M.
Spacious Modular Rental on Huge Horse and Cattle Farm near Charlottesville, Virginia
A living room with a dark-colored sofa, a glass coffee table, a floor lamp, and a TV mounted on the wall.

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

Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.
Gordonsville
9.4 out of 10, Exceptional, (39 reviews)
"Beautiful place"
United States
Berhan S.
Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.
An outdoor patio area with two wicker chairs and a small table, surrounded by a stone wall and a white fence.

12. “The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.

“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
Gordonsville
10.0 out of 10, Exceptional, (38 reviews)
"Absolutely lovely place to stay. Stunning views and conveniently located to so many of the local attractions. Will definitely come back someday."
United States
Kirby R.
The price is €292
includes taxes & fees
31 Oct - 1 Nov
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
A cabin with a wooden deck, a staircase leading to a door, and a forested background.

13. Romantic A-Frame for 2 w/ Hot Tub + Fire Pit

Romantic A-Frame for 2 w/ Hot Tub + Fire Pit
Unionville
10.0 out of 10, Exceptional, (1 review)
The price is €280
includes taxes & fees
20 Oct - 21 Oct
Romantic A-Frame for 2 w/ Hot Tub + Fire Pit
A two-story house with a porch, a front door, and a small garden with a pumpkin.

14. Charming 3-Bed Cottage on Main Street in Historic Gordonsville

Charming 3-Bed Cottage on Main Street in Historic Gordonsville
Gordonsville
9.8 out of 10, Exceptional, (19 reviews)
"This was the cutest house! Our favorite of our weeklong roadtrip. Perfect for our 6 adults. Close to town, which was adorable also. Would love to come back and stay again!"
United States
Cheryl G.
The price is €328
includes taxes & fees
28 Oct - 29 Oct
Charming 3-Bed Cottage on Main Street in Historic Gordonsville
A geodesic dome structure with a wooden deck and two Adirondack chairs.

15. Private luxury dome with hot tub & fire pit.

Private luxury dome with hot tub & fire pit.
Unionville
The price is €370
includes taxes & fees
1 Nov - 2 Nov
Private luxury dome with hot tub & fire pit.
A bedroom with a bunk bed, a desk with a chair, and a window with blinds.

16. Classic Cottage Rental on Huge Horse and Cattle Farm near Charlottesville

Classic Cottage Rental on Huge Horse and Cattle Farm near Charlottesville
Gordonsville
The price is €265
includes taxes & fees
20 Oct - 21 Oct
Classic Cottage Rental on Huge Horse and Cattle Farm near Charlottesville
A bedroom with a bed, a chair, a table, and a cabinet.

17. 1856 Manor Vacation Rental on Huge Horse and Cattle Farm near Charlottesville, Virginia

1856 Manor Vacation Rental on Huge Horse and Cattle Farm near Charlottesville, Virginia
Gordonsville
The price is €577
includes taxes & fees
17 Nov - 18 Nov
1856 Manor Vacation Rental on Huge Horse and Cattle Farm near Charlottesville, Virginia
A rural landscape with barns and a green field.

18. Charming Cottage Overlooking Gorgeous Citation Bass and Bream Pond near Charlottesville

Charming Cottage Overlooking Gorgeous Citation Bass and Bream Pond near Charlottesville
Gordonsville
The price is €268
includes taxes & fees
20 Oct - 21 Oct
Charming Cottage Overlooking Gorgeous Citation Bass and Bream Pond near Charlottesville
A spacious living room with a large beige sectional sofa, two blue armchairs, a wooden coffee table, and a floor lamp.

19. Boardwalk Hotel on Lake Anna by Kasa

Boardwalk Hotel on Lake Anna by Kasa
4.0 star property
Louisa
9.0 out of 10, Wonderful, (149 reviews)
"A very nice place. Very clean and comfortable. Would definitely stay again."
United States
Stephanie
The price is €112
includes taxes & fees
3 Nov - 4 Nov
Boardwalk Hotel on Lake Anna by Kasa
A cabin with a dining table set for a meal, a bicycle, and a sign indicating the name 'Vangelis'.

20. Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
2.5 star property
Stanardsville
9.4 out of 10, Exceptional, (147 reviews)
"Loved everything about my stay, customer service was amazing and I’m definitely making this an animal visit!"
United States
Promise
The price is €176
includes taxes & fees
17 Nov - 18 Nov
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Orange County Hotel Reviews

Holiday Inn Charlottesville-Univ Area by IHG

Holiday Inn Charlottesville-Univ Area by IHG

8/10 Good
"The Fri t desk guy was excellent. He was there when we checked in late afternoon and also when we checked out late morning which made me wonder about staffing. He was friendly, knowledgeable and professional. The property and room were clean but dated. The site says it has a restaurant and bar but there is not. Breakfast was very mediocre. The usual hotel eggs, potato’s and waffles were fine but the rest was cold. The biscuits were literally cold. And no orange juice? Overall I’d stay again for location but temper my expectations for anything other than a clean safe room."
Sammi 1-night trip
Posted 1 hour ago
Holiday Inn Charlottesville-Univ Area by IHG

Find out more about Orange County

Holiday Homes in Orange County

Search for holiday homes in Orange County on Expedia.ie! You can easily find your home rentals, villas, holiday apartments in Orange County using one of the methods below: 

  • View our selection of featured holiday homes in Orange County
  • Use the map to find apartments and other holiday rentals in the Orange County neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday homes in Orange County while they last

Look no further and take a look at our great range of rental properties in Orange County!