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

Orange Vacation Rentals

Q: What's the top vacation rental that Orange has to offer?

Lakeside Comfort: 6BR w/ Game Room : This vacation home rental outside of Orange offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. You and your friends and family can relax into your vacation with amenities like a hot tub.

Dates

November 2026

December 2026

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Our top choices for Orange vacation rentals

A house with a brick chimney, a small window, and a wooden deck.

1. Newly renovated entire guest suite in Orange County.

Orange

vishal k.

AED 571 total

includes taxes & fees

9 Nov - 10 Nov

A living room with a fireplace, a chandelier, and a sofa.

2. The Pembroke Room in the historic Holladay House

Orange

Robert

AED 1,005 total

includes taxes & fees

8 Nov - 9 Nov

A hallway with wooden flooring, a staircase with a wooden handrail, a chair, a table with a lamp, and a wall-mounted painting.

3. The Blenheim Suite in historic Holladay House

Orange

Merrie Mac S.

AED 1,224 total

includes taxes & fees

8 Nov - 9 Nov

A grassy field with a wooden fence, trees, and a distant building.

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

Gordonsville

William J.

AED 638 total

includes taxes & fees

9 Nov - 10 Nov

A spacious living room with a large beige sectional sofa, two blue armchairs, a wooden coffee table, and a floor lamp.

5. Boardwalk Hotel on Lake Anna by Kasa

Louisa

Josh

AED 464 total

includes taxes & fees

11 Nov - 12 Nov

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.

Gordonsville

Tracy

AED 615 total

includes taxes & fees

8 Nov - 9 Nov

A grassy field with three wooden Adirondack chairs and a wooden table.

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

Gordonsville

AED 770 total

includes taxes & fees

8 Nov - 9 Nov

A glass enclosure with a view of a forest interior, including a bed and various plants.

8. Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Stanardsville

Rachel

AED 695 total

includes taxes & fees

7 Dec - 8 Dec

A grassy field with four wooden Adirondack chairs arranged in a semi-circle.

9. Elegant Cottage on 600 Acre Horse & Livestock Farm

Gordonsville

Todd R.

AED 926 total

includes taxes & fees

9 Nov - 10 Nov

A wooden cabin with a deck, surrounded by a grassy area and a flowering tree.

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

Gordonsville

Jeff C.

AED 991 total

includes taxes & fees

9 Nov - 10 Nov

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.

Gordonsville

Berhan S.

AED 843 total

includes taxes & fees

8 Nov - 9 Nov

A cabin with a wooden deck, a staircase leading to a door, and a forested background.

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

Unionville

AED 1,112 total

includes taxes & fees

9 Nov - 10 Nov

A hallway with a wooden bench, a red door, and a framed picture on the wall.

13. Historic Madison Eagle Inn

Madison

Tracy

AED 881 total

includes taxes & fees

1 Dec - 2 Dec

A modern kitchen with a microwave, bar stools, and a trash bin.

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

Gordonsville

Kirby R.

AED 1,124 total

includes taxes & fees

8 Nov - 9 Nov

A wicker basket with brochures on a glass table, a white vase with white flowers, and a white chair in a room with a window.

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

Gordonsville

Jeanna S.

AED 1,282 total

includes taxes & fees

9 Nov - 10 Nov

A forested area with a fire pit and Adirondack chairs.

16. Moonfire Farm Shenandoah region cozy getaway

Barboursville

Matt

AED 747 total

includes taxes & fees

8 Nov - 9 Nov

A living room with a stone fireplace, black leather sofa, and a flat-screen TV mounted on the wall.

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

Gordonsville

B S.

AED 1,541 total

includes taxes & fees

12 Nov - 13 Nov

A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a glass dining table with chairs.

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

Gordonsville

Stephen M.

AED 2,030 total

includes taxes & fees

8 Nov - 9 Nov

A two-story house with a stone facade, a front porch, and a well-maintained lawn.

19. Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+

Stanardsville

Jason

AED 678 total

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with wooden cabinets, a dining area with stools, a flat-screen TV mounted on the wall, and a cozy seating area with a patterned rug.

20. The Ranch at Wine Country - Complimentary Bottle!

Gordonsville

Marisa G.

AED 1,584 total

includes taxes & fees

9 Nov - 10 Nov

View all properties

Find vacation rentals that suit your style

Top Orange Hotel Reviews

A large, two-story building with a symmetrical facade, multiple windows, and a central entrance.

Inn at Willow Grove

Orange

10/10 Excellent

Anonymous traveler

Mayhurst Inn

Orange

10/10 Excellent

Casey is a remarkable host, delivering with her family, a very high quality experience! No amenity was overlooked. The property is in excellent condition; the grounds and setting, interesting and historical; the breakfast scrumptious and memorable; and the nearby downtown city of Orange afforded very good restaurant access. Simply, the best B & B experience we have had the pleasure to enjoy, thanks to Casey's and fam's effort!

Edward

A swimming pool with a blue and white color scheme, surrounded by a lounge area with seating and a staircase.

Hampton Inn By Hilton Gordonsville

Gordonsville

10/10 Excellent

The hotel is modern, clean, and convenient, and it's a great value. The staff, especially the General Manager Mr. Abdul Rab, is a gem. **pedia basically screwed up this booking due to website errors during payment ("Oops, something went wrong on our end, please try again"). They ended up booking the hotel five times, all on the wrong dates which had apparently re-loaded from the previous cached page for the booking I had just completed at a different hotel, for the day before this one. What a...

Norm

A modern hotel lobby with a central bar area, seating arrangements, and a coffee station.

Hampton Inn & Suites Culpeper

Culpeper

10/10 Excellent

Nicholas

A covered porch with a rocking chair and a table with a vase of flowers.

Prospect Hill Inn & Restaurant

Louisa

10/10 Excellent

This is a charming bed and breakfast. Anmenities are high end, so is the service. We stayed in a room circa 1752. The bedding however was more recent and very luxurious. The grounds are impeccable, with flowers and trimmed hedges everywhere. There are fields and even a little nature trail in the woods on the property. Its ideally located in Virginia wine country and in proximity to the homes of three past presidents, all of which you can visit. If you feel like shopping or eating out,...

Yves

A stone fireplace with a wooden mantel, a window above it, and a table in front with a vase of flowers and candles.

Stevenson Ridge

Spotsylvania

10/10 Excellent

We stayed here after attending a wedding on the grounds. The Post Office is the sweetest little cabin. We had a wonderful fire in the fire place, the bed was to die for, and in general, it was one of the most peaceful and cozy little places we have stayed. Stevenson Ridge didn't miss any of the little details, right down to delivering breakfast in a basket the next morning. We'll definitely come back!

Jen

A modern cafe with seating arrangements, a counter, and a large window providing a view.

Holiday Inn Express & Suites Charlottesville by IHG

Pantops

10/10 Excellent

James

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Stanardsville

10/10 Excellent

Kookju

A hallway with a wooden floor, a potted plant, and a door on the right.

Culpeper Center Suites

Culpeper

10/10 Excellent

Dan

A swimming pool with multiple lanes, lounge chairs, and a table with chairs.

Holiday Inn Express Hotel & Suites Culpeper by IHG

Culpeper

10/10 Excellent

Erin

A large, elegant building with multiple balconies, a well-lit lawn with tables, and a grand staircase.

Keswick Hall

Keswick

10/10 Excellent

Louis

A hotel room with two beds, a sofa, a coffee table, and framed pictures on the wall.

Comfort Inn & Suites Charlottesville Hollymead Town Center

Hollymead

10/10 Excellent

This is a brand new property and very clean. We had a larger suite with the small pull out sofa. Overall we are a family of five and I always notice the size of a room and this one was on the larger size. If you have younger children they would have room to play on the floor. The breakfast was typical but stocked, clean, and decent. My teens ate without complaints. The staff was friendly and accommodating. We left a piece of jewelry behind, realized it about an hour later and called and...

Billie

A building with a brick facade and white columns, a brick pathway, and a door with a wreath.

The Estate at Meander

Locust Dale

10/10 Excellent

Anonymous traveler

An outdoor patio area with a fire pit, seating, and a pergola structure.

Staybridge Suites Charlottesville Airport by IHG

Hollymead

10/10 Excellent

James

Frequently Asked Questions

Are there vacation rentals in Orange?

Yes, we give you a choice of vacation rentals in Orange near The Arts Center in Orange, or you can go with a secluded option if you want a relaxing stay. Orange is known for its wineries and museums. Make sure you have time to check out the cafes and art during your trip.

What's the top vacation rental that Orange has to offer?

Lakeside Comfort: 6BR w/ Game Room: This vacation home rental outside of Orange offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. You and your friends and family can relax into your vacation with amenities like a hot tub.

How many vacation rentals are there in Orange?

Expedia has 37 vacation rentals for your stay in Orange.

What can I see and do in Orange?

Rapidan River and Lake Anna are a couple of scenic spots to enjoy the outdoors, whereas James Madison Museum is one of the cultural attractions. Other places in town to visit include James Madison's Montpelier and The Arts Center in Orange.

What are vacation rentals like in Orange?

Vacation rentals are privately owned accommodations you can book for a few days or a quick weekend in Orange. Vacation rentals provide amenities like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for family gatherings.

Orange Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Orange vacation rentals

1. Newly renovated entire guest suite in Orange County.

2. The Pembroke Room in the historic Holladay House

3. The Blenheim Suite in historic Holladay House

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

5. Boardwalk Hotel on Lake Anna by Kasa

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

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

8. Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

9. Elegant Cottage on 600 Acre Horse & Livestock Farm

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

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

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

13. Historic Madison Eagle Inn

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

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

16. Moonfire Farm Shenandoah region cozy getaway

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

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

19. Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+

20. The Ranch at Wine Country - Complimentary Bottle!

Find vacation rentals that suit your style

Top Orange Hotel Reviews

Inn at Willow Grove

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Orange?

What's the top vacation rental that Orange has to offer?

How many vacation rentals are there in Orange?

What can I see and do in Orange?

What are vacation rentals like in Orange?