
Orange Holiday Rentals
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
Our top choices for Orange holiday rentals

1. Newly renovated entire guest suite in Orange County.
Newly renovated entire guest suite in Orange County.
2. The Pembroke Room in the historic Holladay House
The Pembroke Room in the historic Holladay House
3. The Blenheim Suite in historic Holladay House
The Blenheim Suite in historic Holladay House
4. Lake access w/hot tub, game room,boat slip, kayaks & more
Lake access w/hot tub, game room,boat slip, kayaks & more
5. Boardwalk Hotel on Lake Anna by Kasa
Boardwalk Hotel on Lake Anna by Kasa
6. Servants' Cottage on 600 Acre Working Horse/Cattle Estate
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
7. Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
8. Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
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
10. Elegant Chalet on a 600-Acre Horse and Cattle Ranch
Elegant Chalet on a 600-Acre Horse and Cattle Ranch
11. '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.
12. A-Frame for 2 | Hot Tub | Detached Bath
A-Frame for 2 | Hot Tub | Detached Bath
13. Historic Madison Eagle Inn
Historic Madison Eagle Inn
14. 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.
15. Moonfire Farm Shenandoah region cozy getaway
Moonfire Farm Shenandoah region cozy getaway
16. “The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
17. Charming 3-Bed Cottage on Main Street in Historic Gordonsville
Charming 3-Bed Cottage on Main Street in Historic Gordonsville
18. Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
19. Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
20. The Ranch at Wine Country - Complimentary Bottle!
The Ranch at Wine Country - Complimentary Bottle!Find holiday rentals that suit your style
Top Orange Hotel Reviews

Courtyard by Marriott Charlottesville
Find out more about Orange
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Orange holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Orange. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Orange. Seeing all the best attractions is bound to make you fall in love with Orange. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Orange short-term rentals, that won’t be hard to do.
Explore a world of travel with Expedia
- B&B in Orange
- Cabin Rentals in Elkwood
- Holiday Homes in Madison
- Resort in Syria
- Apartments in Syria
- B&B in Unionville
- Cottages in Keswick
- Motels in Woodville
- Chalets in Stonewall-Hawthorne
- Villas in Stonewall-Hawthorne
- Reva Hotels
- Remington Hotels
- Hotels near Charlottesville-Albemarle
- Culpeper Hotels
- North Downtown Hotels
- Glenora Hotels
- Hotels near Warplay Paintball
- Syria Hotels
- Zion Crossroads Hotels
- Keswick Hotels
- Hotels near Belmont Farms Distillery
- Louisa Hotels
- Charlottesville Hotels
- Hotels near Birdwood Golf Course
- Barboursville Hotels
- Madison Hotels
- Woodville Hotels
- Banco Hotels
- Lignum Hotels
- Brandy Station Hotels
- Locust Grove Hotels
- Gordonsville Hotels
- Orange County Hotels
- Aroda Hotels
- Elkwood Hotels
- Hotels near Downtown Mall
- Mitchells Hotels
- Orange Hotels
- Lahore Hotels
- Mineral Hotels
- Troy Hotels
- Stanardsville Hotels
- Leon Hotels
- Rochelle Hotels
- Belmont Hotels
- Hotels near Swift Run Gap Entrance Shenandoah
- Hotels near James Madison's Montpelier
- Boston Hotels
- Trevilians Hotels
- Oyo Rooms Hotels in Charlottesville
- Wyndham Hotels in Syria
- Pet Friendly Hotels in Keswick
- Romantic Hotels in Syria
- Ski Hotels in Syria
- Pet Friendly Hotels in Charlottesville
- Luxury Hotels in Boston
- Flights to Charlottesville
- Flights to Culpeper
- Flights to Syria
- Flights from Wichita Falls (SPS) to Charlottesville (CHO)
- Flights from Houston (IAH) to Charlottesville (CHO)
- Flights from Leesburg (LEE) to Charlottesville (CHO)
- Flights from Kings Canyon (KBJ) to Charlottesville (CHO)
- Flights from Auckland (AKL) to Charlottesville (CHO)
- Flights from Charlotte (CLT) to Charlottesville (CHO)
- Flights from Gaya (GAY) to Charlottesville (CHO)
- Flights from Hanoi (HAN) to Charlottesville (CHO)
- Flights from Reva
- Flights from Keswick
- Flights from Zion Crossroads
- Flights from Brightwood
- Flights from Charlottesville
- Flights from Syria
- Flights from Louisa
- Flights from Gordonsville Municipal
- Lake Anna State Park
- Fashion Square Mall
- Downtown Mall
- Lake Anna Winery
- John Paul Jones Arena
- Aroda Holidays
- Charlottesville Holidays
- Orange Holidays
- Swift Run Gap Entrance Shenandoah
- Belmont Farms Distillery
- Syria Holidays
- Visit Lake Monticello
- Visit Glenora
- Visit Earlysville
- Visit Free Union
- Visit Banco
- Visit Aroda
- Visit Trevilians
- Visit Louisa
- Visit Ruckersville


































































