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

Cottages in Orange County

Compare and save

  • 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

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Top Cities in Orange County

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

Barboursville

Barboursville

Our top choices for Orange County cottages

A bathroom with white subway tiles, a window with white curtains, a framed picture on the wall, and a showerhead.

1. Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Ivy
10.0 out of 10, Exceptional, (59 reviews)
"It was a couple very cozy place for us to stay in the perfect location."
United States
Linda W.
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
A deck with two chairs and a table overlooking a scenic landscape with mountains and a cloudy sky.

2. Relax at 3100 feet and enjoy the peace and tranquility

Relax at 3100 feet and enjoy the peace and tranquility
Free Union
10.0 out of 10, Exceptional, (98 reviews)
"My parents said they had the best weekend! Raving about the views and the trip, Thank you so much!"
United States
Morgan S.
Relax at 3100 feet and enjoy the peace and tranquility
A single-story house with a front porch, a small deck, and a well-maintained lawn.

3. Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries

Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
Troy
9.2 out of 10, Wonderful, (150 reviews)
The price is AED 551
AED 786 total
includes taxes & fees
19 Oct - 20 Oct
Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
A wooden deck with a table and chairs, a potted plant, and a view of the landscape.

4. Charming Cottage on beautiful Farm & Vineyard

Charming Cottage on beautiful Farm & Vineyard
Keswick
9.8 out of 10, Exceptional, (50 reviews)
"Loved staying here and look forward to another trip soon. Beautiful setting and unique property. Was clean and as advertised. Loved the winery. Definitely looking forward to next stay! Thank you! "
United States
Sheila S.
Charming Cottage on beautiful Farm & Vineyard
A rustic wooden cabin with a porch, surrounded by dense foliage and a stone pathway.

5. Unique Cypress cottage, close to Charlottesville with mountain views.

Unique Cypress cottage, close to Charlottesville with mountain views.
Charlottesville
10.0 out of 10, Exceptional, (67 reviews)
"Great stay, very friendly, responsive owners."
United States
David F.
The price is AED 551
AED 1,058 total
includes taxes & fees
12 Nov - 13 Nov
Unique Cypress cottage, close to Charlottesville with mountain views.
A hot tub with a view of a green landscape and a white fence.

6. Cowboy hide-a-way cottage with hot tub on historic farm close to everything

Cowboy hide-a-way cottage with hot tub on historic farm close to everything
Charlottesville
9.6 out of 10, Exceptional, (37 reviews)
Cowboy hide-a-way cottage with hot tub on historic farm close to everything
A hot tub and deck area with a view of a lake, surrounded by trees and a wooden fence.

7. Stonemont Farm Cottage with Hot Tub! in Keswick near Vineyards

Stonemont Farm Cottage with Hot Tub! in Keswick near Vineyards
Keswick
9.8 out of 10, Exceptional, (40 reviews)
"We had a wonderful stay at The Cottage! Everything was as described. We spent a lot of time outside by the hot tub or in the rocking chairs. The kids loved seeing all the deer in the evening and looking for fish in the pond. We can’t wait to stay here again in the future!"
United States
Amber W.
Stonemont Farm Cottage with Hot Tub! in Keswick near Vineyards
A residential property with a gravel driveway, a wooden fence, and a well-maintained lawn.

8. Peaceful Light-Filled Cottage Close to Charlottesville

Peaceful Light-Filled Cottage Close to Charlottesville
Charlottesville
10.0 out of 10, Exceptional, (55 reviews)
"Very peaceful and comfortable place to stay."
United States
Fiona
Peaceful Light-Filled Cottage Close to Charlottesville
A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

9. Charming Cottage Near Vineyards

Charming Cottage Near Vineyards
Charlottesville
10.0 out of 10, Exceptional, (11 reviews)
"Loved this place for a short getaway. Great location!"
United States
Nicole M.
The price is AED 1,447
AED 1,976 total
includes taxes & fees
30 Oct - 31 Oct
Charming Cottage Near Vineyards
A wooden deck with a round table and chairs, a bench, and an umbrella.

10. Robinson River Roost - Country cottage near Shenandoah NP

Robinson River Roost - Country cottage near Shenandoah NP
Madison
10.0 out of 10, Exceptional, (45 reviews)
Robinson River Roost - Country cottage near Shenandoah NP
A white building with a stone pathway leading to the entrance.

11. Loveshack, a charming tiny house on a 5 acre farm

Loveshack, a charming tiny house on a 5 acre farm
Charlottesville
8.8 out of 10, Excellent, (15 reviews)
"House was clean and organized. The host was very nice and attentive to our needs. "
United States
Ryan A.
Loveshack, a charming tiny house on a 5 acre farm
A wooden deck with a glass table and white chairs, surrounded by a forest.

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

Charming 2-bedroom cottage in lovely Madison with WiFi, AC
Madison
9.8 out of 10, Exceptional, (25 reviews)
"We enjoyed our stay, we loved the property and location, so beautiful!!"
United States
Kelly M.
Charming 2-bedroom cottage in lovely Madison with WiFi, AC
A small, single-story building with a blue roof and white walls, featuring a porch with steps and a flagpole with an American flag.

13. Bluebird Cottage A: Across from Lake Monticello, Near Charlottesville, 1 Dog Ok

Bluebird Cottage A: Across from Lake Monticello, Near Charlottesville, 1 Dog Ok
Palmyra
10.0 out of 10, Exceptional, (49 reviews)
"Wonderful place to stay! The cottage was beautiful and location was perfect! Highly recommend! "
United States
Chyenna R.
Bluebird Cottage A: Across from Lake Monticello, Near Charlottesville, 1 Dog Ok
Three Adirondack chairs on a grassy field with a mountain in the background.

14. 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 AED 551
AED 733 total
includes taxes & fees
14 Oct - 15 Oct
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
A modern house with a covered patio, outdoor seating, and a well-maintained lawn.

15. Charming Eastham Guesthouse

Charming Eastham Guesthouse
Charlottesville
10.0 out of 10, Exceptional, (12 reviews)
"Great place we loved it! "
United States
Al B.
The price is AED 533
AED 819 total
includes taxes & fees
21 Oct - 22 Oct
Charming Eastham Guesthouse
A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

16. Classic Virginia Cottage, 10 min to UVA and Vineyards

Classic Virginia Cottage, 10 min to UVA and Vineyards
Charlottesville
The price is AED 1,359
AED 1,855 total
includes taxes & fees
25 Oct - 26 Oct
Classic Virginia Cottage, 10 min to UVA and Vineyards
A cabin with a porch, surrounded by trees and a swing set.

17. Cozy Rixeyville Cottage w/ Deck, Grill, & Stabling

Cozy Rixeyville Cottage w/ Deck, Grill, & Stabling
3.0 star property
Rixeyville
Cozy Rixeyville Cottage w/ Deck, Grill, & Stabling
A single-story house with a front porch, a green door, and a small attached garage.

18. Fire Pits, Creek View: Historic Virginia Farmhouse

Fire Pits, Creek View: Historic Virginia Farmhouse
3.0 star property
Bealeton
2.0 out of 10, (1 review)
"The location was absolutely stunning — one of the most beautiful places I’ve stayed, and the house itself was just as lovely. Everything was clean, peaceful, and true to the photos. Unfortunately, the host experience wasn’t as positive. She lives next door and sent additional rules at the last minute, then seemed to scrutinize us throughout the stay. I’m 28, and she made a comment about my age that gave the impression she was uncomfortable with younger guests. It was disappointing because we...
United States
Madeline
The price is AED 430
AED 1,546 total
includes taxes & fees
23 Oct - 24 Oct
Fire Pits, Creek View: Historic Virginia Farmhouse
A brick building with a white staircase and an American flag.

19. 1802 cottage once part of Monticello and owned by Thomas Jefferson

1802 cottage once part of Monticello and owned by Thomas Jefferson
Charlottesville
9.4 out of 10, Exceptional, (118 reviews)
"Steve was a wonderful host! The property is beautiful and the cottage cozy. Thank you for sharing your farm oasis with us."
United States
Joy M.
1802 cottage once part of Monticello and owned by Thomas Jefferson
Exterior

20. An elegantly appointed house tucked in the Virginia Mountainside.

An elegantly appointed house tucked in the Virginia Mountainside.
Stanardsville
An elegantly appointed house tucked in the Virginia Mountainside.
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

Sonesta ES Suites Charlottesville University

Sonesta ES Suites Charlottesville University

10/10 Excellent
"Wonderful staff, excellent room, great breakfast, and an unbeatable location! We will stay here again the next time our travels bring us to Charlottesville."
Sarah 2-night trip
Posted 3 hours ago
Sonesta ES Suites Charlottesville University

Explore a world of travel with Expedia